Episode 134: James Holt – Building Trust in Tech Sales

​​Seasoned sales experts can often come from uncertain starts and tough transitions. In fact, James Holt, now a successful Strategic Account Executive at Cockroach Labs, found the beginning of his sales journey to be entirely daunting and overwhelming.  

In this episode of Tech Sales is for Hustlers, James shares an overview of his career trajectory in sales thus far, recounts the ways in which building trust has been the foundation of his largest deals, and explains how he evaluates new tech sales opportunities when considering a career pivot.  

Guest-At-A-Glance

💡 Name: James Holt

💡What he does: Strategic Account Executive

💡Company: Cockroach Labs

💡Noteworthy: James transitioned from oil and gas to tech sales, becoming a top global rep at Grafana and landing the company’s first seven-figure deal.

💡 Where to find James: LinkedIn 

Key Insights

Overcoming Initial Panic in Tech Sales

James shares his initial experience in tech sales, where he felt overwhelmed by technical jargon and industry terms. He describes his first sales kickoff as a panic-inducing event where he felt out of his depth. However, he persevered and gradually built his confidence and expertise. This insight highlights the importance of resilience and continuous learning in tech sales, even when faced with daunting challenges.

Building Trust Leads to Larger Deals

James recounts his time at Grafana, where he landed the company’s first seven-figure deal. He emphasizes the importance of building trust with clients, sharing a story where he left a family dinner to resolve a client’s major issue. This incident led to larger deals down the line, demonstrating the value of commitment and customer service in tech sales.

Evaluating Opportunities in Tech Sales

James discusses his approach to evaluating new opportunities in the tech sales industry. He shares his thought process and the factors he considers when deciding where to go next in his career. This insight provides valuable advice for tech sales professionals on how to navigate their career paths and make strategic decisions.

Episode Highlights

Transitioning from Oil and Gas to Tech Sales 

James discusses his transition from the oil and gas industry to tech sales. He describes the initial panic he felt when he was exposed to technical jargon and industry terms. Despite feeling overwhelmed, James persevered and gradually built his confidence and expertise.

“I’m sitting in this room with no tech experience listening to these people throw out industry terms and jargon and technical stuff that I have no idea what they’re talking about. And I remember sitting in the keynote thinking, ‘I’ve made a terrible mistake.”‘

Building Confidence in Tech Sales 

James shares his journey of building confidence in tech sales. He talks about how he gradually settled into his role and how each conversation and objection he faced helped him improve and develop his confidence.

“And so the next call, you’re a little better, and then you hear another question. And every day, you inch forward and build your confidence up.”

Landing a Large Software Company 

James recounts his experience of landing a large software company as a client. He emphasizes the importance of commitment and execution in building trust with clients.

 “I landed a large software company in San Francisco. The guy, we’re in the meeting, and he says, ‘Everything you all are saying sounds great. I’ve seen this time and time again before I signed the deal, and then I can’t get you on the phone.’ And I told him, I was like, ‘Okay, listen, I understand that. I’m telling you that if I commit to something, I will execute.”‘

Evaluating the Next Opportunity 

James discusses his approach to evaluating new opportunities in the tech sales industry. He shares his thought process and the factors he considers when deciding where to go next in his career.

“In terms of what I look for, one, the tech has to be solid. I don’t care that you landed customers. How many times have they expanded with you? What’s your net dollar retention? That’s what the VCs are looking at. […] And so, look at your net dollar retention. If you’re evaluating a company, if you’re in it for the equity and earning potential, make sure that they’re landing customers, but then expanding within, call that whatever your sales cycle is, but realistically within the next 12 months. They’re doing bigger deals with you more frequently and in different divisions because that’s how you know if you can’t do that, you’re not gonna be successful.”

Transcript:

[00:00:00] James Holt: the best sales reps you’re ever going to meet, the ones I’ve ever met, are still excellent at the SDR function. Even though they’ve been an inside or they’ve been an enterprise rep for 5, 10, 20 years, they’re still hammering the phones themselves.

[00:00:12] They’re still sending their own emails, they’re still sending LinkedIn requests, they’re all doing that. And then just what the SDR brings them is just like icing on the cake, 

[00:00:20] Marc Gonyea: James Holt in the house. Christopher Country Roads, take 

[00:00:45] Chris Corcoran: me home. 

[00:00:46] James Holt: Good to see you guys. 

[00:00:47] Chris Corcoran: Great seeing you. The pride of West Virginia’s in the big Apple. Yeah. A far a far 

[00:00:53] Marc Gonyea: cry from Beckley, dude. Yeah. You’re good to see you, James. 

[00:00:56] James Holt: Yeah. Great seeing you. I think it’s been, what, five, six years? It’s been a while.

[00:01:01] I’m trying to look at it right now. Yeah, it was 20 16, I think. January, 2016. Yeah. 

[00:01:04] Chris Corcoran: Seven years. Okay. Time flies. It does, it does. I can’t wait to kind of hear your story and share it with our listeners. Happy 

[00:01:12] Marc Gonyea: to share. Before we get into that, well, let’s kick off the story. Okay. I always think of the business story, but we, there’s a personal story too.

[00:01:18] Yes. Tell us a little bit about where you’re from, where you grew up, what you like as a kid, just a little bit of that 

[00:01:24] Chris Corcoran: stuff. Oh God. Yeah. The 

[00:01:26] James Holt: good stuff, right? Yeah. Yeah. So I’m from, uh, Southern West Virginia town called Beckley. And, you know, grew up, went to school in West Virginia, had, uh, No idea, really.

[00:01:36] I was leaning towards law school, right. Did a semester of law school and decided, you know, that wasn’t really for me. and left and actually went well. Who were you like 

[00:01:44] Chris Corcoran: as a kid? What was that like as a kid? Yeah, that’s James. All the bad stuff. 

[00:01:48] James Holt: Yeah. Yeah. I don’t know. I got decent grades in school, was always pretty, at school, but I was always in trouble.

[00:01:53] Always like, oh really? I talked all the time. I never got recess. 

[00:01:57] Chris Corcoran: I just, yeah. I, I did 

[00:01:59] James Holt: not have a good run with it. Right. So siblings, siblings? Yeah. I have a younger sister who is two years younger than me, and then a younger brother who’s 10 years. Okay. Wow. So pretty, pretty big age gap. 

[00:02:09] Marc Gonyea: So you’re the oldest and you were chatty, chatter it in class all 

[00:02:13] Chris Corcoran: up talking all the time.

[00:02:14] James Holt: Okay. Right. couldn’t sit still. So all of that, that comes with it. So, yeah. Always in trouble a lot, but, you know, got good grades as best as I could. Right. Yep. And, don’t know what else you want to go. 

[00:02:24] Marc Gonyea: Any idea? Well, what you like in the high school, did your, did you work? You a kid who played sports, you know, some people have jobs, some people play sports, some people are really in the school.

[00:02:32] Like, and then what did you think you wanted to be when you 

[00:02:35] James Holt: grew up? Yeah, so my dad actually owns, plumbing and HVAC company. Okay. And so, I like sports. All right. Yeah. But I was always like really money driven, even from a young age. There you go. and so I actually went to work and I started working for him full-time when I was 12 in the summers.

[00:02:49] So I would do, 

[00:02:50] Chris Corcoran: okay, see this is, 

[00:02:50] Marc Gonyea: this is a good stuff. Trying 12 past 

[00:02:52] Chris Corcoran: this stuff. Yeah. Okay. 12. 

[00:02:54] James Holt: 12. What are you doing for him? Digging ditches. would you, would you know how to prom? very, I can’t. I can get by. Okay. I’m, I’m, I’m handier than most people. Yeah. Uh,but I’m nowhere near, I wouldn’t, I wouldn’t build a house for you.

[00:03:06] Okay. So could you do H V A C work too? Very little. I can run duct work. Okay. And stuff like that. But, uh, the electricals and components and stuff like that, again, I wouldn’t, I wouldn’t, 

[00:03:16] Chris Corcoran: let’s still run. You’re, you’re 12 years old running duct work. 

[00:03:18] James Holt: Yeah. Duct work, digging ditches, picking bags of concrete up all the jobs that no one else wanted to do.

[00:03:24] So you give to the kid right. To, to go over the less tenured guy. 

[00:03:27] Chris Corcoran: This, this portion of the episode is dedicated to my son Baron. Yeah. Who needs to be doing this stuff on this course? No, 

[00:03:34] James Holt: no. Stick with sports. My brother had it figured out. He was really good at sports. They never made him get a 

[00:03:40] Chris Corcoran: job. Right.

[00:03:40] So, 

[00:03:41] Marc Gonyea: but you said, you said you were money driven. Was that because you, did you get 

[00:03:44] Chris Corcoran: paid for these things? Oh yeah. Yeah. Okay. 

[00:03:46] James Holt: Because I mean, when you work construction, right. Especially back then, you know, you got paid Yeah. A lot more than minimum wage. Yeah. Even at that time, and especially if you’re doing contract work for the government and stuff like that, you can get.

[00:03:56] pretty decent salary, so I got my first real paycheck and especially at 12, I had no bills. Well, yeah. You 

[00:04:01] Chris Corcoran: know, so dude, 

[00:04:03] Marc Gonyea: somebody call Eddie 

[00:04:03] Chris Corcoran: Nye. Yeah. Yeah. Well, he’s money driven. We’re the labor department job yet. 

[00:04:07] Marc Gonyea: Yeah. Right. So, okay. Andy Barrett on this podcast. Wait, so well, what do you think the money, so having money at a young age, kind of like, did it give you?

[00:04:14] Like a sense of what Independence or like, well, 

[00:04:17] James Holt: accomplishments, you know, that, but also at the time Right. I was like, I’ve got so much money for video games. Right. And stuff like that. Yeah. Right, right. Um, they took all the money without really me knowing about it out of the bank and used it to start a college fund, which was probably better than Yeah.

[00:04:30] Blowing it on video games. Yeah. Yeah, it was cool. Okay. It was, uh, I started working. For him for a couple years, realized really didn’t want to go into manual labor. That was just not gonna be me. Yeah. and then just had a number of different jobs. I was a ski instructor in high school where during the winter it was a place called Winter Place.

[00:04:47] So you probably Yeah, yeah, yeah, yeah, yeah, yeah. winter Place I grew up 15 minutes from there. Oh wow. Kids back 

[00:04:52] Chris Corcoran: there. That’s right. Okay. Yeah. So I 

[00:04:54] James Holt: was ski instructor lifeguard during the summer, and you’re always making money. Yeah. Worked at a bowling alley. Love it. Full time. Just a bunch of odd jobs.

[00:05:01] Chris Corcoran: Right. 

[00:05:02] Marc Gonyea: Yeah, man. Piecing it together, man. So, what’d you think you wanted to be then? So your dad’s a business owner. Yeah. Right. I dunno if your mom worked or not, but mm-hmm. You know, what did you think you wanted when you grow up? 

[00:05:12] James Holt: I always from a young age wanted to be an attorney. Okay. That was always my goal was I was gonna law school when I went.

[00:05:18] And what, what, why? I was really, really still am into politics. Okay. Um, I interned at the House of Commons in London in undergrad. I did a number of like page duties, you know, you call it the state legislature. Yeah. I just had tons of internship experience and. Did my, you know, university research, all politics, right?

[00:05:35] So like I wanted to go, you know, get a law degree, then go, you know, I don’t know, work for a lobbying firm, go work on the hill. Something like that is what I envisioned. I see. 

[00:05:43] Chris Corcoran: okay. And then the recession happened. Oh, 

[00:05:45] Marc Gonyea: but no, sales. Sales didn’t even like Mm. Sales didn’t, nobody was in the family was in sales.

[00:05:51] I mean, dad’s a business owner, but like tech sales you are doing now. That wasn’t 

[00:05:54] Chris Corcoran: even, like, 

[00:05:55] James Holt: the funny thing is I, when I look back on it, I didn’t even know tech sales was a thing. Mm-hmm. Like I know there’s sales, like door to door sales or you know, you sell products, this or that. For some reason I just never put two and two together that like Yeah.

[00:06:07] Technology companies, when you sell to businesses actually also have to have sales reps. Right. It was not even a thing until, you know, until after the oil and gas thing. And then we got 

[00:06:16] Marc Gonyea: connected. We’ll get, we’ll gonna get to that. So, cuz people want to know about this. I’m always curious people who do something else before they come to Memory Blue.

[00:06:23] Mm-hmm. You can do some perspective and, and some take some things that other people don’t have. Yeah. And there’ll be people who might be listening to this podcast cause you look at your LinkedIn and say, oh, this guy did something else before memoryBlue wasn’t even tech sales. Yeah. Alright, so you, you went 

[00:06:35] Chris Corcoran: to law school for a semester.

[00:06:37] So you went to wvu, sorry, went WVU undergrad. And then did you go to WVU Law school? Correct. So you stay in Morgantown. Mm-hmm. Have one semester Yep. Of law school and said no. Yeah. What was it about it? 

[00:06:49] James Holt: So, you know, this was just a few years after the session. The job market overall was terrible. I actually really liked law school.

[00:06:56] the summer before I started law school, I interned, interned, at an oil and gas company. Okay. and was working there. And really this was a company that was out, you know, doing land contract negotiations for drilling rights, things like that. And then I was just kind of doing the intern thing, like getting copies was down in Texas.

[00:07:16] Chris Corcoran: This was in West Virginia? In West Oil and Gas in West Virginia. 

[00:07:18] James Holt: Oh yeah. Okay. Oh yeah. West Virginia, a big natural gas state. Oh, fracking. Fracking. Fracking. 

[00:07:23] Marc Gonyea: Yeah. The Pennsylvania too. 

[00:07:24] James Holt: Yeah. But yeah, so I, I interned there and just saw the money really, that people were making, you know, working for an oil company and was like, oh, okay.

[00:07:30] Especially during a time when people were, you were crushing it. Yeah. scrounging for jobs at the time. So went to law school and started going through, actually had a good run for the first semester at least I enjoyed it. but really started looking at the student loan debt. I was racking up. Okay.

[00:07:43] And then The, the starting salary for at that time, realistically that you could look at for an attorney was half of what they were paying people and oil and gas with just a college degree. Right. And so at the time, you know, I just looked at it and said, well, what am I doing here? I’m gonna be in a mountain of student loan debt.

[00:07:59] you know, whether or not it was the right decision, you know, we’ll see 

[00:08:02] Chris Corcoran: business. So it became a business decision at that point. Of course. Always 

[00:08:05] James Holt: right? Yeah. Yeah. Yeah. It’s always about 

[00:08:06] Chris Corcoran: the money. so you shut it down, you shut down law school and just go into oil and gas full-time. And what were you doing for the oil and gas company?

[00:08:14] James Holt: So for the oil and gas company, I started out doing just like what we, I you could call a tech project, but it was basically putting an onlines record database together for them so they could do land research. Okay. at a faster pace. Yeah, I know it wasn’t very technical, right?

[00:08:27] It was just kind of like, you were the most technical, you were the young people in the office, right? New computers better than this. Like put something together. Um, and so once we finished that up, it was pretty successful. I really liked talking to people and negotiating, like why I wanted to go be a lawyer.

[00:08:42] Yeah. And so they had a division where you are the representative of the company interacting with either, you know, Individuals that are mineral owners, you know, attorneys, banks, that own mineral rights, property, whatever it is, and you negotiate the contracts, right? Hey, we want to drill this specific area.

[00:08:59] you know, what’s it gonna take, what’s the dollar per bonus? What’s the royalties? Here’s the terms and conditions, you know, you have that kind of thing. So I went in and did that for two years for them. Okay. That sounded fun. Yeah, it was a lot of fun. I mean, it was interesting, right? You were, yeah, most of the time doing stuff over the phone, but you were like driving out, you know, into the middle of nowhere sometimes meeting with people and discussing contracts.

[00:09:21] had people give me that you could go negotiate contracts, you have dinner, they’ve got, you know, vegetables from the garden. I had one guy that had a vineyard that gave me bottles of the wine he was making. So you saw a lot of really, like, interesting things I thought I would never experience, you know?

[00:09:35] Marc Gonyea: so how did you end up a memoryBlue? 

[00:09:37] James Holt: So do you remember Christian Morrie? Yeah. Yeah. So Christian. Yeah. Yeah, 

[00:09:42] Marc Gonyea: I remember. I remember our interview. Yeah. 

[00:09:44] James Holt: So right around the end of 2015, the oil and gas market collapsed. Yep. The prices just plummeted and they started having layoffs across the board and it like spooked me, right?

[00:09:53] Because it was, you know, we went from a company, when I started, we were 70 employees pre I p o started working there, and then four years later, 600 employees post i p o, tremendous success. And then overnight they laid off 65% of the workforce. Very simple. Cyclical. Yeah, very cyclical, right? It was my first experience of that cyclical nature.

[00:10:13] When you see it firsthand, it’s like, wow. Like this is not something I really, I think, wanna do with the rest of my life, you know, my career. And so again, oil and gas was always a money driven decision. What else makes money? You know, tech and oil and gas at the time were the two main contenders. It was like, oh, how do I get into tech?

[00:10:31] And Christian and I actually did study abroad together and undergrad cuz he went to WVU. Yep. And you know, I was talking with him and, um, he’s actually married to a girl from my hometown. Okay. So we stuck together and kind of, you know, or, uh, 

[00:10:45] Marc Gonyea: who went to law school? huh Her, I’m sorry, Christian’s, Christian’s wife is from your, 

[00:10:49] Chris Corcoran: uh, yeah.

[00:10:49] James Holt: Yeah. And she went to law school. She went law school. Yep, yep, yep. She’s an attorney. and, uh, yeah, he said, well, what do you know about tech, tech sales? And I was like, I don’t know, you sell Facebook. Like, what are you talking about? Yeah. Yeah. I don’t know what he’s talking about. Yeah. Yeah. And he was like, well, if you’ve never heard of it, like this is a very, very lucrative career.

[00:11:05] Right. You should look into it. And so I started doing research, you know, back then, early days, I think it was like Glassdoor. Mm-hmm. And then just kind of web searching and looking and being like, how much money are these people making? Yeah. Without any kind of specialized degree. Like this can’t be real 

[00:11:17] Chris Corcoran: without any really skill.

[00:11:18] Any skill. Yes. Any skill persons doing this. Yeah. Yeah. Listening. Yeah, he’s listening. I’m joking. Put me in a headlock or 

[00:11:25] James Holt: something. I owe you big time. but yeah. Yeah. So we, we, you know, obviously start talking to me about it and you know, at that point it was the decision there. Christian Moore, did you hit the 

[00:11:34] Marc Gonyea: bell?

[00:11:34] Yeah, I’m just trying to keep up. Okay. Sorry, I’m taking two steps ahead. 

[00:11:38] James Holt: he, uh, you know, we started talking about it and looked at it and that’s where you start to make the decision. Right. As I started to understand the process better. Okay. What is an sdr? What is corporate inside sales? What is field enterprise sales?

[00:11:49] All that stuff. Like, and how do you get it? Obviously enterprise sales is where traditionally the money’s made, so Uhhuh, how do I get there as quickly as possible? Mm-hmm. and so Christian actually right. Worked at Memory Blue the year before. Mm-hmm. I joined, he was already out and working and making really good money.

[00:12:03] Mm-hmm. Um, at the company he was at. know, it was the pitch there. We were saying, Hey, listen, like. You know, your career, right? Is a marathon, not a sprint. And you really want to go somewhere where you can get the foundational skills that you need in order to be successful here, right? Because of you.

[00:12:19] I don’t, the best way to say it is if you jumpstart a couple of levels, right? Like maybe you get a higher base salary, but you’ve lost all that knowledge that you would’ve gained going from start to finish. And actually what would’ve made you a more well-rounded rep? Right? So we got introduced and uh, you know, that’s when, uh, we were doing the interviews and I was driving back and forth from West Virginia to DC Yeah.

[00:12:39] Then coming back and forth from Beth? No, from Morgantown? No, from, so it was about three and a half hours. It wasn’t bad, but I remember I would’ve the interview with you all then go to Bing, Nickowski and then back. And then when we decided, yeah, Nikowski, when I decided to take the job, I was doing that then.

[00:12:54] Plus having to drive like furniture and stuff and get an apartment in DC It was a, it was a crazy time. I 

[00:13:00] Marc Gonyea: remember being like, man, we’re land this guy. Yeah, right. But, but this time with that too, because, Your, like you said, your career’s not linear. It’s just not always going up, up, or you know, this way, whatever.

[00:13:12] Was it tough for you to kind of, because we got, it’s, you took from doing some interesting things to take an entry level sales job. Yep. So is that, is that something, you know, some cognitive dissonance you had to resolve? Or 

[00:13:23] Chris Corcoran: was it, 

[00:13:23] James Holt: the money was the big thing, right? Yes. Again, like, I, I didn’t particularly care.

[00:13:26] Like Texas is exciting. it was an exciting opportunity, like, again, just to get in the door somewhere, you know, like I, I was very excited about that. I wasn’t over, you know, that wasn’t my big concern. It was, okay, how do we, how do I readjust my life from the oil and gas days to the pool? Having to, yeah, knowing that the, the end goal or like as you get established is even more lucrative than oil and gas ever would’ve been, right?

[00:13:50] but yeah, how, how am I gonna survive these next couple of years while I get established in it? Yeah. That was my biggest kind of concern. So you just, live and lean for a few 

[00:13:57] Chris Corcoran: years? Yeah. 

[00:13:58] Marc Gonyea: What was that hard to do? Yes, 

[00:14:00] Chris Corcoran: yes. It was very hard to do. 

[00:14:02] James Holt: Very hard to do because I mean, when I was working at memoryBlue, I was getting my MBA too from Penn State.

[00:14:07] Yeah, right. So I was like, I was like taking calls during the day and at night I was going home and reading and doing all my assignments over the weekends, and then going right back to the phones on Monday. That was a, that was a tough year, you know? Busy time. Yeah. Yeah. It was good. But, wouldn’t wanna relive it.

[00:14:21] You Where the drive come from. man, I have no idea. I think realistically when I look back on it, when you see my, especially my father’s side of the family. Okay. You know, all coming over, all being business owners. I mean, my grandmother ran well, when are you coming over? 

[00:14:36] you 

[00:14:36] Marc Gonyea: just all coming over. 

[00:14:37] Chris Corcoran: Oh, I don’t, they they, they’ve been here for a long time.

[00:14:39] Oh, ok. 

[00:14:40] James Holt: Sure. Ok. I guess they were, you know, Irish immigrants typically, you know, and, uh, but when they came over, they all started their own businesses. Right, okay. Plumbing and all that stuff. Uhhuh. And so when I look back, you know, and you see kind of my dad’s side of the family in particular, my grandfather started his construction company and worked seven days a week.

[00:14:58] They also had a motel that they ran that my grandmother did all the financials, the books for, and then ran that. And then him and my aunt were working there after school and on the weekends to clean the rooms, do all that stuff. And, um, it’s a grinders, yeah, yeah. Just that, you know, whatever you wanna call Protestant, old school work ethic Yeah.

[00:15:16] Kind of thing. That’s what they were all about. Right? Yeah. You know, you work seven days a week. Yeah. 

[00:15:20] Chris Corcoran: that’s just what the holds do. Yeah. This is what we do. You gotta survive. You beat. 

[00:15:23] Marc Gonyea: Yeah. Right. Okay. Wow. What was it like transitioning into what we do? You know, what you, what memory Luke did? What you did when you started?

[00:15:31] Yeah. Because you had, that’s like, talk about the experience. 

[00:15:34] James Holt: so going through the interview process, right. Bendikowski really Hit him off. Cuz if you ever have a conversation with him, you know he is very quick talker. Yeah, right. Like very kind of, on the bond. I was like, okay. I think this guy, yeah, me, me and him are gonna work out, you know?

[00:15:47] Yeah. but I don’t know if you remember this, but my first day at Memory Blue actually was sales kickoff for Mark Logic. In DC at the, that’s the, that’s 

[00:15:55] Chris Corcoran: the type 

[00:15:56] Marc Gonyea: of stuff we did back then, Chris. Yeah, yeah, yeah. His 

[00:15:58] Chris Corcoran: first day. 

[00:15:59] James Holt: Yeah. USA Today building. Yeah. Remember you were there and Ben was there. Yeah.

[00:16:04] Marc Gonyea: and I remember we were both there for a reason, just to make sure that this guy from West Virginia didn’t mess anything up. Yeah. You 

[00:16:09] Chris Corcoran: know, and I 

[00:16:09] James Holt: panicked you. What? What? What’s that? I panicked. You did. So I came from oil and gas not knowing anything about the tech market really, other than what I could research.

[00:16:17] And you get to the first, my first sales kickoff, you’re sitting in a room with people from all over the world and not only, you know, when you know about MarkLogic, which was a NoSQL database, databases are tough in general, right. Very technical products. Yes. MarkLogic was a new age database that was even more technical.

[00:16:34] Yeah, yeah, yeah. Right. So I’m sitting in this room with no tech experience listening to these people throw out. Industry terms and jargon and technical stuff that I have no idea what they’re talking about. And I remember sitting in the keynote thinking, I’ve made a terrible mistake. No man, we knew you’d be 

[00:16:50] Marc Gonyea: good.

[00:16:51] We would’ve not have, I would’ve not brought you to that. Yeah. If I had not thought Ben and I had not thought you were, you were gonna go. Oh. But it is overwhelming. Oh, it was overwhelming, 

[00:17:00] Chris Corcoran: right? 

[00:17:00] James Holt: Yes, I knew. Uh, yes. And then, you know, you go and you meet all these people and it was a really great event. But I do remember the first couple of days being like, think I’m in over my head this time and I think I may just need to just disappear, you know, before they find out that I have no idea what I’m doing.

[00:17:14] Chris Corcoran: And 

[00:17:15] Marc Gonyea: the 

[00:17:15] Chris Corcoran: only way you got through that was like, man, if Christian Mor can do this, man, why you doing that? 

[00:17:23] Marc Gonyea: Enter the bus. Oh yeah, I’ll give you CORs address, but keep going in that transition was 

[00:17:31] Chris Corcoran: just you and the other guys on the campaign 

[00:17:33] Marc Gonyea: Then. 

[00:17:33] Chris Corcoran: No, cause you have No, cuz I 

[00:17:35] James Holt: mean, who was, it was Wes, junket.

[00:17:37] Was member there. Oh, animal. Yeah. Andrew. Uh, Lisar. Oh yeah, remember that was, yeah. 

[00:17:43] Chris Corcoran: Yeah. 

[00:17:43] Marc Gonyea: Oh yeah. He’s another cool. He’s good. 

[00:17:45] James Holt: Yeah. Good. Yeah. Yeah. Mike Kenny, and, uh, Connor Bebe came along afterwards. Him later. Okay. All right. but no. Right. We had the whole, whole kind of team there you know, I mean the, the training is actually what really, really helped and kind of calm me down a little bit because I so much always wanna go into something and just understand what I’m doing and just hit the ground running, whereas, Part of the training, not only for Memory Blue, but Mark Logic at the time, right? Was like, Hey, you’re gonna go through these training modules, you’re gonna break it off piece by piece by piece every day. You’re gonna learn a little bit more. I think it was, you know, several weeks before I made my first call, even for Mark Logic, cuz the first month almost was all just 

[00:18:21] Marc Gonyea: training on they had us, they were very just a, which is good on us putting our people through their, their, their, their process.

[00:18:27] Chris Corcoran: Yeah. 

[00:18:27] James Holt: Yep. Which is good. Yeah. Super helpful. And then, between the kind of training and reinforcement that you got every day, going through those training technical modules, but then also during those call blitzes, right? Sitting in the, the aisle and listening to the other reps that had been there.

[00:18:44] Yeah. Um, Annette Cole, right? Another one. Yeah. she was there. just listening to them kind of go through their pitch and hearing what customers were saying and learning and like saying, okay, here’s the technical module I just went through. These are what these terms mean. And then hearing them used.

[00:18:58] In a real world situation. Mm-hmm. Day by day. Right. Your confidence grows. and so I, you know, first week or two were pretty rough. And then I would say, as you know, time went on. I settled down a bit and it, things got a little bit easier. That’s so funny 

[00:19:11] Chris Corcoran: that you 

[00:19:11] Marc Gonyea: were there and Tony, what people remember and I was probably, I was there.

[00:19:14] Yeah. But you know, you didn’t tell me that if you did, it probably just blew, blew you off. Yeah. Oh, no, no. I definitely 

[00:19:20] Chris Corcoran: would’ve told you I was panic. 

[00:19:21] Marc Gonyea: I’m panicking. You made a terrible decision. Yeah. But, and that’s what people remember, right? Because it can be overwhelming, but you, you know, obviously settled in.

[00:19:29] When you got, when you started doing it, when did you kind of think, okay, I made the right decision? Was there a moment in time when you’re like, or it just happened gradually, or I think it happened 

[00:19:39] James Holt: gradually. I know, yeah. I don’t know what else we can. What we can really say. But I do remember, you know, settled in gradually and started, you know, you have one conversation and then an objection comes up and you’re not sure quite how to handle it or what, what the person’s even talking about from a technical nature.

[00:19:54] Cuz when you’re calling in for Mark Logic or any of those companies, those database companies, your, your audience you’re speaking to is very technical, right? Yeah. And so I think like, Hey, I got this objection. And then, you know, somebody sitting next to, you’d be like, when they say that, you know, this is what it means, this is what you should say, these are the questions you should ask.

[00:20:10] And so the next call, you’re a little bit better and then you hear another question, right? And every day you kind of inch forward and,you know, get, you know, build your confidence up. But I do remember, I think it was actually early in my tenure, I can’t say the company I think, but I actually.

[00:20:23] Created an opportunity for one of the reps that was seven figures that actually did end up closing once I joined the company. Oh, wow. Um, and I remember once, we had that conversation, I passed it to the rep and the guy was like, okay, this is actually real. Like that’s a, that’s a big get and that was with a Fortune 100 company.

[00:20:40] once I saw that and saw the progression of the deal and having the rep talk to me about it and seeing how it’s going, I was like, okay, I can do this. Right. Like, I can make it. 

[00:20:49] Marc Gonyea: I always drive by the office driving the airport in the bay right on the side of the road. Mm-hmm. You’re going, going Carlsbad.

[00:20:56] Mm-hmm. Yeah. And I think of you, I forgot about Wes. My bad. Wes and I think about, Mike and Connor and Ben and Frank. Was Frank Taylor the manager on it. When you. 

[00:21:08] James Holt: He was right. Frank? Yeah, Frank Taylor was, he was a rep when I first joined and I think very quickly cuz Ben moved over, right? Mm-hmm.

[00:21:15] Into a different mm-hmm. Team, I think. Right. Did he, I can’t remember. 

[00:21:19] Chris Corcoran: Yeah. Yeah. Was Frank also 

[00:21:20] James Holt: a manager? But Frank got promoted after Ben left, as I recall. Yes. Uh, but yeah, so that would’ve probably been the last six months, I think it 

[00:21:27] Chris Corcoran: was a split. 

[00:21:28] Marc Gonyea: When you’re doing this role, then, did you start to look at, okay, what, what happens next?

[00:21:32] Because you were friends with Christian, so Christian by the time had been doing other things, but did you start to envision yourself as an AE or something else? Or what was kind of going through your mind as you were learning it? 

[00:21:41] James Holt: Absolutely. As an ae. I remember I was. Like every ounce was consumed and getting hired out by MarkLogic.

[00:21:47] Mm-hmm. My client. Right. And like, going through and meeting folks that I did, I used to go actually with a couple of the engine, like I would have their calendars right? Because we were working closely with them. And I would see when like engineers or like executives and stuff from MarkLogic would be in the DC area, I would message them, ask if they wouldn’t mind getting coffee with me and stuff.

[00:22:05] I actually met a few of, their leadership before I ever joined the company just by saying, if you, where are you gonna be? Give me 15 minutes, I’ll come to you. Right? Yeah. And would go meet with them. And I actually had several of the, of the executives do that. They were super helpful. I was like, what does it take, what are you looking for?

[00:22:21] Kind of if you had career advice for somebody that’s just getting started, what would you do? That kind of stuff. And I think, you know, over time building that reputation up, like with, your client, right? Kind of. Mm-hmm. When, when we all got transferred, because they. Took my contract, Mike’s contract in Connors, right?

[00:22:36] Yep. At the same time. So I think, you know, it was just this kind of that, right? Like, just knowing I wanna be an ae. What’s it gonna take? You know, I’ll go the extra mile to make it happen. Who told you to do that? well, personally I would always just do that naturally. Right. but I do know, yeah. I mean, of course that was always stressed at memoryBlue, right?

[00:22:56] Like 

[00:22:56] Chris Corcoran: No, no, no, no. My point is, is 

[00:22:57] Marc Gonyea: no one told you to do that. No, you do that yourself. Yeah. You do that 

[00:22:59] Chris Corcoran: yourself. Oh, 

[00:23:00] James Holt: you always would reinforce that though. Yes. Like, you know, client relations helping, especially when you’re talking about your, maybe your first job outta college. Right. You know, you need some polish, you need, some guidance and things like that.

[00:23:09] I mean, it was always stressed. 

[00:23:10] Marc Gonyea: Right. You said I was trying to compliment you. Yeah. Yeah. So, thank you. Yeah. The, uh, but it’s, I think it’s for you cause you had this job before, you know, outta undergrad and you, your MBA and you were working for us, so you had a different perspective than other people Yeah.

[00:23:25] Who were coming up. Like, this is my first job, right? Outta school. 

[00:23:27] James Holt: Yeah. Well, I was older, right? Yeah. Most of the folks. And there were 23, 22 maybe. You know, when I was there I was 26. Right. Yeah. So, yeah, I. 

[00:23:35] Chris Corcoran: I felt like the old guy at the time. Right. 

[00:23:36] Marc Gonyea: I that much older, but Yes. But, but that’s like, that’s like 

[00:23:40] Chris Corcoran: 10 years.

[00:23:41] Yeah. It’s like 10 years, 

[00:23:42] Marc Gonyea: two, three years of work 

[00:23:43] Chris Corcoran: experience versus, versus two or three days work experience. Yeah. Yeah. Right. I mean he’s, he’s already been doing, he’s been oil and gas 

[00:23:51] Marc Gonyea: contact. How, how did that work? Experience help, help or shape what you were doing? Was it what you just said? Hey, I was focused on maybe MarkLogic will convert me.

[00:24:00] Yeah. So to speak. Was that, how did that work 

[00:24:02] James Holt: experience help you? I think, realistic cuz you’d already been in an office environment, right? Yeah. And you’d already seen like how you’re supposed to present yourself to executives, what you’re gonna do, frankly, corporate politics, that kind of stuff, right?

[00:24:12] Like kind of understanding how that works. but then also I think one of the things that was really helpful from that perspective was, it’s nerve wracking. Typically, you know, anytime you do it, but especially when you first get started picking up the phone and calling people that you’ve never met before.

[00:24:26] Right. And striking up conversations and building interests. Like it’s, it can be terrifying, right? Absolutely. Yeah. And so I think because I had come from an industry where I was already calling people, Hey, you don’t know me. I represent a company. I’d like to sit down with you and talk about X, Y, and Z for a contract, for drilling rights.

[00:24:45] You know, it wasn’t necessarily a one-to-one transition, but I was already kind of versed in striking up conversations and calling people who had never heard of me before. Right. So I think I may have had a little bit of an easier time with that transition, but it still didn’t mean it was easy because I do remember, okay, now I’m not calling people to talk about how I’m going to give you money and we’re going to do a contract.

[00:25:06] Now I’m trying to call you about you giving me money. Right. So that’s a completely different, it changed the way you do 

[00:25:12] Marc Gonyea: stuff. Yeah, exactly. Your day, it changed 

[00:25:14] Chris Corcoran: your lucky day. 

[00:25:17] Marc Gonyea: What did you get good at at, at that process, the outbound process? What did you kind of make, what was your superpower?

[00:25:24] Everybody’s good at certain things on the phone. Yeah. What was, what was the James Holt like, you know, signature. 

[00:25:30] James Holt: don’t know about so much signature. I, I agree cuz I, I’ve been through so many trainings where like, this is the way you have to do things. Right. And I just never like that because you listen to successful people.

[00:25:41] Right. And you think about all the people that I came up with through Memory Blue mm-hmm. That are successful, all have completely different styles. Yeah. Yeah. So there’s no one size fits all. I always, I didn’t like that. Yeah. I think, what I was really good at, and I still think what I’m really good at is that, you know, I’m pretty good at listening to customers.

[00:25:59] Right. Like when they’re talking to you. The main thing is, is like, one of the things you really have to learn, especially in sales, is like, You have to manage your relationships. You’re going to be, if you’re gonna be in this in the long haul, it’s a small world, right? Mm-hmm. You’re going to be selling, I still sell to the same customers that I’ve sold to now for three different companies.

[00:26:14] Right? Yeah. Because you’re in a focused, in a database market. I’m really good at listening. I, I feel like, at least to what customer problems actually are. And then kind of pivoting the conversation of like, okay, is this a good fit or not? I mean, you have to walk away sometimes, right? Of course. Yeah. but just really understanding what they’re trying to accomplish, whether or not you’re a good fit.

[00:26:34] And then honestly, just providing value. I mean, we all kind of know one thing that MongoDB was very good at stressing was that, you know, you come to a meeting prepared. Don’t just, you know, call it show up and throw up, right? You waste people’s time. It puts a bad taste in your mouth. Make sure you’ve done the research on who the people, like the people you’re meeting with are as much as you can, the companies you’re talking to, all that other stuff.

[00:26:54] And have an idea of the questions that you’re gonna ask prior to the call to make sure that People understand that you’re respectful of their time, right? You’re taking time out of your day to meet with me to discuss this. So I’m pretty good at that aspect of it, of getting people to open up and start talking about some of the problems they have, cuz that’s can be a struggle.

[00:27:09] Right? Yeah. Sometimes you don’t wanna share troubles you’re having with your systems or whatever it is with a, a sales rep on a phone that you’ve never met with, right? Correct. and then the other thing, this was actually going back again to the customer success side that I did for Mongo. Yeah. one of the things that I’ve gotten really good at, and it’s actually worked out very much in my favor, is that, I don’t cut and run.

[00:27:30] Right. I think historically there’s been kind of a way of like, Hey, the deal is closed, the sales rep’s done now customer success, you people, whoever it is, you come take it over. I’ll talk to you again when you wanna buy something or there’s a renewal, I. Try to stay on every customer success call. I attend every meetings with customers that buy.

[00:27:49] I see. I know exactly what’s going on, and I’m there every step of the way. And then when I do some, when I say I’m gonna do something, you execute on it. Right? Yeah. And so I think that’s, that’s been kind of, that, that’s been super helpful for me. I see. Yeah. 

[00:28:02] Marc Gonyea: We’ll get to that part. Yeah. Yeah. We’ll, so 

[00:28:05] Chris Corcoran: I think one of the reasons why, and tell me if you agree or disagree that you’re so good at, getting people to open up to you is because you have credibility.

[00:28:14] Yeah. I would hope. Right? Well, no. So you some in somehow, some way you are showcasing that you’re credible. Mm-hmm. Because people don’t just open up to anybody. Like if they don’t have any credibility, why am I gonna, why am I gonna waste my time? Exactly. But they know somehow that you’re credible. Mm-hmm.

[00:28:28] And that’s what really helps open, have them open up. Yeah, I would, I would 

[00:28:32] James Holt: hope so. I mean, but yeah, you’re exactly right. How do you build credibility? How do you build credibility? I mean, you come prepared, right? Yeah. I mean, we can all think probably back to, calls you’ve listened to or projects that have gone wrong where you see how many, even you pro, you guys probably get pitched all the time by products, right?

[00:28:50] Mm-hmm. From, from different sales rep. You can tell the difference from someone that’s just sent you a blind email without even looking anything about it, versus someone that says custom tailored, specific, you know, I know what you guys are doing. Congratulations on the growth this or that. You’ve got these new markets, X, Y, and Z.

[00:29:05] This is what other customers of mine are experiencing in your situation. Yeah. It comes off much more polish. Okay, now you’ve got my attention. You now you’re, you’re worthy of me at least giving you 

[00:29:15] Chris Corcoran: Yeah. I’ll, 

[00:29:15] Marc Gonyea: I’ll spend some time. Yeah, exactly. You’re cashing that check. Yeah. With the right, the right people will recognize that as yep, as instant credibility.

[00:29:22] They’ll give you, 

[00:29:23] Chris Corcoran: A moment. Credibility 

[00:29:25] James Holt: is key, especially early on. You can build credibility over time as you get deeper, but it’s imperative that you do it from the outset as soon as you possibly can, because otherwise you’re not gonna get to that next level or that next stage, that next meeting.

[00:29:37] Chris Corcoran: Exactly. 

[00:29:38] Marc Gonyea: Yeah, exactly. All right, so you’re, you’re at memory blue. You’re doing your, how long were you with us? One year. One year you’re executing with us and then the opportunity to go to work for MarkLogic came up. How did that happen? 

[00:29:49] James Holt: So, uh, it was January, 2016, right? Yeah. At the year mark, right? Yeah.

[00:29:54] And then Memory Blue decided to bring everything in house from an SDR perspective. Mark Logic. Yeah. Or Mark Logic. Yeah. I’m sorry. Yeah. Mark Logic decided to bring everything in the house from a SDR perspective. And, they took mine, Mike and Connor’s contracts meeting to work with them internally. And at that time, they didn’t really have an idea of what inside sales was gonna look like.

[00:30:14] It was. But you were like, I’m doing it. 

[00:30:16] Chris Corcoran: Oh, 

[00:30:16] Marc Gonyea: I’m doing it. Yeah, I’m 

[00:30:17] Chris Corcoran: in, of course. Yeah. That this is why I’m 

[00:30:18] James Holt: here. Yeah. So, okay. They, I, I entered in, it was like a, it was a hybrid role, right? I was still an SDR for AEs that were in the field. However, if there were smaller companies and smaller deals that weren’t necessarily worth an a’s time on the, in the field, I could take those over and run with them myself.

[00:30:36] and so I did that for, you know, about a year. Right? And Connor, Mike and I, we all worked together in that office at the USA Today building. Yep. You know, building out what the S D R function internally was gonna look like, for the team, trying to close deals where we could, you know, it was very difficult because they didn’t even have a go-to-market strategy really for that segment of the market at the time.

[00:30:57] but yeah, did that for about a year. Closed, at, towards the end of my tenure, one deal finally. you know, and that was about the time I realized, okay, I may have hit my ceiling here just cuz they had not built out Yeah. A credible path forward for people in my position. So I was like, I need to go somewhere a little more established that has this function already built out, career projection into the field.

[00:31:17] Chris Corcoran: And there’s a 

[00:31:18] Marc Gonyea: big leap, right? Yeah. You were still earlier in and the other reps are probably like 40 years old. Oh yeah, absolutely. Like classically trained 20 plus years of experience selling big, big, big deals, which Yeah, you gotta work to of course get to that role. Right? So an opportunity 

[00:31:33] James Holt: came along, opportunity came along.

[00:31:35] Uh, my old manager right, uh,reached out to me, for a role at Mongo that I was interested in. Yeah. Because it was a, no, another NoSQL database, but it was open source. A little bit different. Yeah. And funny enough, I had applied, I had just bought a house in the DC area. Yep. Was looking forward to.

[00:31:51] He, he, we had a great conversation and he was like, okay, send me your resume. And I said, okay, can I just come over to your offices? You’re just across the street. And he said, what are you talking about? Like, this role is in Texas. You, this is in Austin. And I was like, oh, okay. I just bought a house in DC I don’t know how much sense it makes to relocate halfway across the country.

[00:32:09] And so he and I spent some time talking over a couple of weeks. This is a 

[00:32:12] Chris Corcoran: guy 

[00:32:13] Marc Gonyea: you met at Mark 

[00:32:13] Chris Corcoran: Logic. 

[00:32:14] James Holt: This was, uh, my. Soon to be manager at MongoDB. 

[00:32:17] Chris Corcoran: Okay, got it. Got, this is completely different. alright. 

[00:32:19] Marc Gonyea: So they, they cold cold got you or whatever? Yeah, on 

[00:32:22] James Holt: LinkedIn, actually. LinkedIn. LinkedIn. And messaged me and I, I looked it up and I said, okay, this actually, I hear about MongoDB all the time.

[00:32:28] Yep. You know, he’s offering me a corporate account executive role. They have this whole thing built out, like this is gonna be a great opportunity. Right. but then he dropped the Austin, Texas piece and I was like, well that sounds great, but like, I’ve got a lot. That’s gonna be a logistical problem for me.

[00:32:41] Yeah. I just bought a place in Northern Virginia. Yeah, exactly. So, you know, he made me a good offer. It was a really great opportunity and so made it work. Right. I just packed, I lived in my house for 90 days. renovated it from renovated from the studs, renovated, completely moved in. 90 days later I was packing up, moving to Texas.

[00:32:58] Did you go, have you 

[00:32:58] Chris Corcoran: ever been to Austin 

[00:32:59] James Holt: before? my first time was for the interview. The, for the interview. 

[00:33:02] Marc Gonyea: And you’re like, okay, maybe 

[00:33:03] James Holt: I can move here. Yeah. Cuz I mean, at that point, The cat was outta the bag. Everybody’s already talking about Austin. Like yeah, there’s gotta be something to that, right?

[00:33:09] Yeah. and so I went down and did the interview and then got to go downtown and see the city and all this. And it was like, okay, this is a cool vibe. I could do this. what’d 

[00:34:20] Chris Corcoran: you do with your house in, you rent it out or sell it? Yeah, rented 

[00:34:22] James Holt: it out for several years. Rented it out and lived in Austin and, uh, you know, went to work for MongoDB and, that was, that was a grind.

[00:34:30] Tell us about it. So, MongoDB, I will say, like, notoriously known, like it is probably one of the best executed sales programs that I know of in the market. is pretty ruthless. it can be, you know, it’s, it’s a challenge, but I will say some of the best reps that I know now in the market, yeah, look at anywhere really, especially in the days, call it, you know, twenty fourteen, twenty fifteen up to.

[00:34:53] Call it 2019, something like that. 2020 around those areas before it is what it is today. If you look and see where those reps go, those companies become extremely successful. Right. Interesting. They have, they kind of wrote the book, in my opinion, in a lot of ways on the way you execute on a sales strategy.

[00:35:10] Yeah. And so that training that they provided there as well was just super intense. very thorough. But I really do think like everybody that came out of it was just, Much better than you went in. Right. And so, I worked for him. I covered a California territory from inside sales perspective out of Texas and did that for about a year and had pretty good success.

[00:35:31] The Southern California tier was very difficult cause you had a free product that people could use. Okay. that they didn’t gate at the time. Right. Okay. So they could just download the enterprise version for free and there was no gate around it and their cloud product hadn’t come along, enough yet to sell.

[00:35:45] So I was in this weird. Kind of limbo where I couldn’t sell them a cloud product just yet, but also the product that can sell to these startups in, in Southern California. Yep. They could get for free. Yeah. And you’d be on the phone with them and you’d, they’d say, oh yeah, we’re using the enterprise version.

[00:35:57] It’s like, well, contractually, you have to pay for that after 30 days. And then they would go quiet Right. And say, oh, no, no, no. Nevermind. We’re using the free version. So, I did make it work. I Yeah. Tooth and nail to my quota. Yeah. there for about a year. And then the manager I really liked, he actually took a field sales role in San Francisco, so he left.

[00:36:18] And, you know, the new manager that came in, I didn’t really jive with Yeah. You know, that was not, it wasn’t gonna be a good fit. Yeah. And so at that point I’d already moved to DC Yeah. For memory blue. Yeah. Now I’ve moved to Texas for another job trying to get to that Yeah. Goal of field sales and now the goal line or the, you know, goalpost is getting moved again.

[00:36:36] And so it’s like, okay, do I. Do I wanna keep doing this or is it, is it worth the stress or the headache? and I had a, a friend I had made that was in customer success, that ran the team there in Austin. And he was like, well, you know, the skills are really transferrable. You know, you could work with our largest customers, some Fortune 100 logos, you could get exposure to how to manage those, you know, fortune 100 accounts.

[00:36:58] And I said, okay, let me think about it. because my other option was I’m gonna have to leave MongoDB Yeah. And start over and inside sales build up the credibility again. Yeah. And at that time, I was halfway through my vest and MongoDB stock, you can look, was just Yeah. On a rip. You know, so it was like, I can’t walk away from this.

[00:37:14] Yeah. and so I guess I’m gonna be in customer success. Right. Like, that sounds exciting. I always wanted to work with the big customers. And you had try some stuff. Yeah, yeah, yeah. And customer success. I did that for about a year. and honestly really liked it. I mean, I, that is one thing I didn’t allude to earlier, but I do think that that’s one of the skill sets I’ve picked up that most AEs don’t have that has made me successful because as the customer success team, you know, you get to see the problems of an implementation or how to put out fires or how to calm customers down when things aren’t going right.

[00:37:43] Right. Yeah. And so I got to see with like a no quota perspective. Yeah. How is it done correctly from this side? Yeah. If you were to manage your relationship, build trust, and expand into account, how do you do that when you don’t have a quota attached to you? Right. Yeah. And so you can do everything, you know, 

[00:37:59] Marc Gonyea: I think it’s fascinating too since you it into sales.

[00:38:02] I wonder if that helped you, how you manage your sales cycles in net new sales too, because maybe you’re selling the people who are suspicious of the technology actually working mm-hmm. From being sold a bill of goods by a salesperson, but like you had the sales experience and the customer success experience.

[00:38:17] Yeah. Then you went back to. Classic sales. Yeah. I kinda think that’s helped that that impacts how you sell. Yeah. Right. Too. 

[00:38:24] James Holt: Absolutely. So for me, and, and I guess we can touch on that, but for me personally, how I choose companies is I make sure to do the research and make sure that the product works Yeah.

[00:38:33] Before I join, because there are tons of products out there that claim a lot of things, and then when you actually go to implement, it does not work. Right. Yeah. 

[00:38:41] Chris Corcoran: I think, I think the technical term for those are 

[00:38:43] James Holt: vaporware, vapor, pressure vapor. So there’s tons of that in the market actually. and so, but yeah, I, I think that’s, that’s a, that’s a good point.

[00:38:52] Like kind of seen from both sides, like mm-hmm. How you land and how do you expand in an account. Right. That’s the main thing. And what you really, I think, wanna look for, right, when you’re talking mm-hmm. About looking at a technology is not really concerned about the land deal. Like that’s gonna be great.

[00:39:05] Good. You get an account, you establish a relationship with a customer. But if you’re going to focus. On these large Fortune 100, fortune 500 companies, the L2, your second, your third, your fourth deal with them, that’s where you really start to see revenue, right? That’s where you see the money.

[00:39:19] Oh yeah. Land and expand. Yeah, land and expand. Everybody’s doing that now, right? Mm-hmm. Like every modern tech company, if you’re not doing land and expand, you know, I don’t know what you’re doing, right? Yeah. But so if you have a product that doesn’t do what it says it does, you land. Then what’s gonna happen is land and leave.

[00:39:34] Yeah, landed, land and leave. Yeah. Yeah, exactly. And then you are going to be fielding calls from angry customers all the time, right? Yeah. I never wanna be a part of a company that does that kind of stuff. Right. Yeah. So I’ve been fortunate so far in that I’ve picked some pretty good companies. but yeah, so I got the experience, you, at least from the customer success side, on really having to build relationships, be there when customers are having problems and helping kind of solve through it, whether it’s you get resources from engineering to come meet with them, or you’re answering, you know, in Slack messages with them, on problems they’re having.

[00:40:03] Right. And so I, I really enjoyed it and had no intentions on leaving. customer success until an old colleague of mine actually ambushed me at the bar in Austin. Which one? Which bar? garage Bar. No. Okay. Garage Bar. yeah, it’s literally in a garage. I 

[00:40:18] Chris Corcoran: don’t know where it is, but it sounds 

[00:40:19] James Holt: like it’s, it’s right by Lavaca.

[00:40:21] You’ve been to Lavaca Street Bar. Yeah. Yeah. Right across. There’s a parking garage that has a bar in it. Yeah. And it’s awesome if you ever get a chance to go. 

[00:40:28] Marc Gonyea: Okay. We’ll, I’ll be there also in two weeks and I’ll track you down. You’re gonna take 

[00:40:31] James Holt: me there? Yeah. Garage bar. All right. Okay. but yeah, so, he had, he had left and uh, was in New York for a while and said, I’m in town.

[00:40:38] Come meet me. I have a, Chris, did you see the 

[00:40:41] Marc Gonyea: theme with this guy? Mm-hmm. Like he built these relationships with people. Christian Mory in the memory blue Oh. Meet in greeting people going above and beyond the memory blue way. Yeah. To meet with the, the people, everyone at Mark Logic, the execs who, who, who, uh, to socialize the idea, Hey, James Holt’s coming over from memoryBlue.

[00:40:58] That’s great. I love that guy. Coffee with him. Right. The Mongo. They, they, they pulled you outta there. But then the Mongo thing into the enterprise sales, I mean into the customer success role. It’s like somebody you met. So tell us about that. Why, how does that happen with you? Is that like you do that on purpose or is it just who, James who James Holt is No.

[00:41:14] Or like, have you, you just do it naturally and you realize it’s important to kind of build your network within the companies you work in? Yeah. 

[00:41:20] James Holt: I mean, it’s probably all the above, right? I mean, think about your value as a sales rep. You, you are a relationship builder, right? Like you are the face of the company.

[00:41:27] Your job is to have a network, build relationships, know the people that you can reach out to, know where to go within the accounts, and also manage, you know, as a sales rep, again, your job is not done when you close the deal. Right now, you’ve got to go through implementations and really at a company, There’s no tech product out there that’s just a silver bullet that you implemented and it’s done right.

[00:41:48] Yeah, that’d be nice. That’s, yeah, it’d be great. It’d be great if it worked that way. I’ll go work for that company exists. but you know, so you need to have credibility. You need to have partnerships, and you need to have relationships internally, right? So you can pull resources because hey, you’re a tech company.

[00:42:03] You’ve got 10 engineers that are all working on another project, and you’ve got seven reps asking them for things, Who’s lever, who, who can you pull? Like can you manage your relationships to make sure your customer’s getting the resources right? Yeah. So there’s just a, I mean, it’s, good for your professional career, for your network, but actually, you know, as an ae your job is to maintain and build relationships internally, externally, it doesn’t matter, right?

[00:42:23] And, 

[00:42:24] Chris Corcoran: yeah. So I got a question. So, uh, at MongoDB. In Austin, you were an inside rep? Yes. Were you working from their o office with other inside reps? Yes. So you could kind of feed off one another? Oh 

[00:42:35] yeah. 

[00:42:35] James Holt: That was the day. Those were the days of when Bitcoin really started taking off too. So I remember the first day I walked into the Mongo sales work corporate office.

[00:42:44] Yeah. Tons of SDRs, tons of corporate sales reps there. And you could see it. They’d have headsets, you’d see people take calls, and then immediately, as soon as the customer call get up, you’d have, you know, buy and answer Coinbase charts up on screens, like amateur crypto traders on the floor. It was, it was a wild year.

[00:43:01] It was a lot of fun. but yeah. Yeah, we were all kind of sitting together so you could hear the feedback. And Mongo was very strict at that time about, you know, your managers were listening in, like, this is what happened. This is what you need to do. You had pre-call preps where you had a doc before you met with a customer.

[00:43:16] Yeah. That said, this is what I’m gonna say. These are the things we’re gonna cover. You had to fill it out like you went to every meeting. Super prepared. So like we talked about you in instill confidence that you know what you’re talking about. 

[00:43:26] Chris Corcoran: Yeah. And so you, it sounds like what a great sales culture.

[00:43:29] Share with us a little bit more, I, I’m sure the listeners wanna know of like what made it such a great sales culture specifically because it sounds like the people that kind of grew up in that sales culture mm-hmm. Are doing some amazing things. So help just describe the sales culture at Mongo. 

[00:43:42] James Holt: So sales culture, I mean, again, you know, it was, it was, it was difficult, right?

[00:43:46] Intense. I mean, you, you had to earn your seat every single day that you were there. Okay. it was a company that was growing rapidly, so they had great talent that was wanting to work there, right? Yeah. So you had to prove your value every single day you were in there. And then also one of the, this is where I actually learned it.

[00:44:00] One of the things that I think is just critical to the success of a business is Mongo’s, philosophy was always a, and this isn’t something I think they invented, but I had first heard it there, which is A players hire other A players, Bs hire. Cs, Cs hire Ds. Oh. Oh. And so the The interview process for Mongo was very intense.

[00:44:19] Okay. I mean, it, my challenge, you know, you have to give a mock presentation on their technology to their executives as your final round. Okay. it took me 24 hours, like not just 24 hours a day, like 24 hours at a desk work to just get that deck to where I thought it should be before I went to present.

[00:44:36] and so they just, they nailed, in my opinion, all aspects of what you really need. Right. You need make sure you’re bringing in the top talent because top talent will also recruit their top talent. Yeah. but then also, you know, you can come through and those people will perform and if you push them, they’ll continue to push and try to do better and, and, and went up.

[00:44:55] So it just was, it became a cycle at that time that really just fed on itself and it kind of just accelerated into, I mean, you can look at their stock performance before the market tanked in 2021, but, uh, it was, it’s just incredible. Yeah. Right. Wow. 

[00:45:08] Chris Corcoran: Sounds like a lot of fun. 

[00:45:10] James Holt: It was a lot of fun. It was very stressful too, though.

[00:45:12] I mean, it was, a very stressful period of life for sure. but yeah, from a, from a professional development standpoint, you know, I would not have changed anything. 

[00:45:20] Marc Gonyea: Does it sound like it? Do you keep 

[00:45:22] Chris Corcoran: it in touch with former colleagues from there? Oh, 

[00:45:24] James Holt: sure. One, uh, the reason I went to Grafana actually was a formal colleague from Mongo.

[00:45:28] Let’s get in this here at the garage bar. So, at Garage Bar? Yeah. Um, I think I’m just gonna see this old friend. Yeah. I walk in and there’s two other people from Mongo there, and I was like, oh, hey guys. People who used to work with, who left? I still worked with them. Oh. 

[00:45:42] Marc Gonyea: You know, at that time. Oh, through the people who, other coworkers.

[00:45:44] Yeah. 

[00:45:44] James Holt: Yeah. So I walked in and it was just like, oh, hey guys, like what are you doing here? I thought it was just catching up. And, the, my friend walked up and said, Hey, sorry to ambush you. my CEO is gonna be here in 10 minutes. We want you to come work for us. I said Okay, nice. I like it. I guess we’re doing this live cuz he had left and went to this very small company called Grafana.

[00:46:04] Yep. Which at the time was I think 35 employees. Mm-hmm. Pre-series A. And so my first impression I started looking them up cuz I’d never heard of them before at the bar on the phone before they got, uh, the CEO there. I was like, okay. So you want me to leave one of the hottest tech companies post i p o in the market to come work for a 32 person series, pre-series A company?

[00:46:24] Yeah. I’m not, I don’t think this is gonna go well, but I’ll have a drink. I’ll get to know you. 

[00:46:29] Chris Corcoran: It sounds like it failed your la your land and leave. 

[00:46:31] James Holt: Uh, yeah, yeah, yeah. I actually, so the CEO’s name’s Raj Dotcoms we really hit it off. I mean, just sat there for, I think I sat and we talked for like two hours.

[00:46:41] Wow. Just about everything. Saying like, you know, here’s what I’ve learned at Mongo, here, here’s the areas that I’m concerned about from a company as early as you are. What do you think the future of this product is? Where do you see you landing? What are your strengths? What are your weaknesses?

[00:46:56] All the things I could think of. Just hammering them questions. Yeah. CEO. The CEO. and one of the things that really, I mean, I loved all the things he had to say, and then when you looked at kind of the metrics around Grafana at that time, again, an open source product, the amount of downloads and the amount of contact requests that they had just to buy the product with no sales team whatsoever.

[00:47:17] I had never seen that before. Okay. And said, okay, there’s something to this. And you start looking at GitHub and you start looking at the stars and the ratings and all this stuff, and just everyone’s talking about Grafana. It’s like, okay. This, you’ve got my attention now. Yeah. and one of the things that really struck me that Raja said, one of the things I, I do get concerned about sometimes, especially with engineering founders.

[00:47:37] Yeah. The company. I think, you know, it’s their baby, right? Yeah. They developed it. and then from an engineering side, maybe they’ve never done sales, probably not. Right. they have some bad habits and some thoughts about how it should work, having never spent time in the seat. Yep. And I always get frustrated by that because I always look at it as saying, I would never tell you in engineering what to do.

[00:47:58] Right. I have requests from customers, but like, I don’t know what it’s like to be an engineer. Right. So I can’t tell you why, why would you ever listen to me when it comes to coding? I, I, I couldn’t do that at all. Yeah. But it seems like that doesn’t always go the obstacles. And I have seen so many times of like, this is how sales should do things and stuff.

[00:48:15] Yeah. And it’s like, well, if it’s so easy, pick up a bag. Yeah. Do it 

[00:48:18] Chris Corcoran: yourself. Right. 

[00:48:19] Marc Gonyea: Why wouldn’t you? We have technical founders tell us how we should execute these outbound sales development campaigns. Yeah, exactly. Like, dude, come on. 

[00:48:26] Chris Corcoran: Yeah. 

[00:48:27] James Holt: Trust us. Yeah. We’re telling you. I know it may seem counterintuitive, but just, you know, trust the process, right?

[00:48:32] Yeah. To pick up a bag. 

[00:48:33] Chris Corcoran: Yeah. Pick up bag. Pick a bag. Yeah. 

[00:48:35] James Holt: Lets prove it out. Pick up a bag. Yeah. You know, but what really sold it to me was, Raj told me, I asked him, and I said, okay, so you’re a technical founder. you know, no real sales experience technically. Right. you know, what do you think about that?

[00:48:46] And he said, well, listen, I, you know, I’ve never done sales before. Like, I don’t know what I know. He was like, we tried to do it ourselves because we’re just, we’re pre-series A. We are trying to bring everything in house. So yeah, we started going through and we could do little small cycles fine, but we started getting into these bigger ones, just organically.

[00:49:02] And we realized like, wow, sales is actually, a lot harder than we thought. You know, there’s a lot that goes into this. And I was like, ok, I can work with that. Yeah. Can work with that. Yeah. Yeah. And so, yeah, I, I met him for coffee the next morning. I threw out a number that I thought was absurd that he would never agree to.

[00:49:18] And he did. Front your top? Yeah. Yes, he did. And he did. And then I put my two weeks in. 

[00:49:22] Chris Corcoran: where were you on your, where were you in the vesting? 

[00:49:24] James Holt: Halfway. Oh, just over halfway through. Oh, so you had to leave? Oh, I left a lot on the table. Wow. 

[00:49:29] Chris Corcoran: Yeah. Yeah. Was it a hard decision to make? 

[00:49:32] James Holt: it, yeah, it was. Had have been.

[00:49:33] Chris Corcoran: It was, but. He crushed it. 

[00:49:35] James Holt: Grafana. Yeah. Yeah. But you have to look sometimes, you know, especially like if you’re, if you’re young enough, you know, you look like it’s the time to roll the dice. Yeah. Right? Yes. and so yeah, it was very hard. It was a very hard decision to leave that money on the table. But the upside on just the experience I would’ve gotten at Grafana, the, the pay structure, the comp, but also the pre-series A equity I got there was like, this is a no-brainer.

[00:49:58] It’s worth taking the risk of this, this equity, you know, risk taker Chris. 

[00:50:03] Marc Gonyea: Yeah. Risk, right? Yeah. Outta college, no law school. Let me go sell oil and gas stuff. Yeah. I remember, I still remember interview. I was like, wait, can you run that by me again? Yeah. And then to come take a sign certificate, pay cut to get in the memoryBlue move to Northern Virginia, right?

[00:50:18] Yeah. Then, move to Austin nine days after buying a place in Northern Virginia. Yeah. And then you just talked about how you were trying to. Trying to preserve your ground at Mongo. Yeah. To preserve the equity, the vesting, and then this is an opportunity. So you, and now you live in New York, which you haven’t gone to that point.

[00:50:34] Yeah. Now I’m in New York. So, so, so why, like, why do you have this view? Because a lot of people won’t live. Risky. Oh yeah. Not like, like how? 

[00:50:45] James Holt: Well, I mean, I, I don’t really have a good answer for that because I know when I told my parents that I was leaving my house in DC that I just bought to move to Texas, they were like, are you having a crisis?

[00:50:53] Yeah, yeah. Or 

[00:50:54] something. 

[00:50:55] Chris Corcoran: What are you doing? Like, you know? Yeah. Like, is it 

[00:50:57] James Holt: wrong with you hun? Yeah. Yeah. You like, can you stay in a city for longer than three years? Yeah. You know, or something. Yeah. So, I, I don’t know. I would just say naturally, even before sales, just in my personal life, I’ve always had a, a higher risk tolerance.

[00:51:11] Yep. I think than most. and so, cuz I do have friends that are in sales too. You gotta be some sort of a risk taker in sales to Absolutely. Cause everything you’re doing is a risk. I know lots of accountants. 

[00:51:21] Chris Corcoran: Yeah. 

[00:51:21] Marc Gonyea: Right. It’s 

[00:51:22] Chris Corcoran: different, 

[00:51:23] James Holt: different mindset. Yeah. And so, but you know, there’s a spectrum to that as well.

[00:51:27] but I, I’ve always been on the end of like, I always want, I was always dollar driven rights. Mm-hmm. That’s why I did oil dollar driven. That’s why I wanna do tech. And so, You know, we’re here to kill it. Right. In my opinion, and the only way to do that is just to go where the opportunity is. Now I know that doesn’t work for everyone, right.

[00:51:44] It’s not, you know, my path doesn’t necessarily mean it’s the right way. Like Right. Honestly, if you can have an easier time of doing it than I did, by all means, like, I encourage you, but, I’ve always just followed where I thought the next best opportunity was Right. For earning. Because at some point you’re gonna get to a point in age, time life where, you just, it’s not feasible to do that anymore.

[00:52:04] Yep. So I looked at that mind view of saying at this particular point of time, before kids, before marriage, any of this other stuff, if that’s what you’re into, that I’m going to go and try to make the best of it wherever I can. Right. Where are your followers? 

[00:52:17] Chris Corcoran: My followers? 

[00:52:18] James Holt: No. Like you don’t wanna follow 

[00:52:19] Chris Corcoran: me?

[00:52:20] Why? 

[00:52:21] Marc Gonyea: It sounds like I do. No, no. I wanna quit memoryblue. Go go to Cockroach or wherever he goes next. Yeah. Right. So you went to Grafana. Yep. Back into a sales gig. Back into a sales gig. And And that why? Just cuz. Cuz you’re like, cause the opportunity, 

[00:52:36] James Holt: the same, same sort thing. If I’m going to take the risk of leaving this equity on the table, I want to cover from a sales perspective, your largest accounts, the biggest banks on the planet.

[00:52:44] The biggest tech companies on the planet’s. The largest logos you’ve got. Yeah. and we just hit the ground running. I was sales rep number four. the second strategic account executive they brought over and, uh, can’t go too much into the logos. Sure. That, you know, is managing some of the largest banks in the world and some of the largest tech companies in the Bay.

[00:53:00] So that first year before Covid in 2019 was just a blast. It was 50 people at a company, hot tech product, and we were doing. You have a meeting in a bank in New York on a Monday, then you have a meeting in the major tech company on Wednesday in San Francisco. Then you’ve gotta be in Atlanta. Like, so we were just flying all over the country meetings, people buying some, I mean that when you look back on it now and you’re like, man, those were the good times.

[00:53:25] Right. I should’ve, yeah. I should’ve enjoyed it a little bit more. Where was the 

[00:53:28] Chris Corcoran: company headquarter? Austin? 

[00:53:28] James Holt: New York. New York. Okay. I don’t know what it is, but the last three companies are all New York open source companies. See, I keep working for New York companies. 

[00:53:35] okay. 

[00:53:36] Chris Corcoran: But unintentional in 

[00:53:36] Marc Gonyea: database space.

[00:53:37] Yeah. Yeah. 

[00:53:37] Chris Corcoran: In the database space. 

[00:53:39] James Holt: Database. Grafana is data visualization. Data visualization is the only one I’ve done that hasn’t been database related. Okay. you know, was individual contributor, there was the number one rep globally? I think it was two years. Mm-hmm. two years in a row. did their, as the company was growing YeahDid the firstst seven figure deal. Landed like six or seven Fortune 100 logos for them. Wow. it was just, it was, it was incredible. Honestly, I’m very, very thankful for that opportunity. 

[00:54:06] Chris Corcoran: and, and, and you got the land part. Did you get the expand part there too? Yeah. That’s 

[00:54:09] James Holt: great. Yeah. Good. Some of their top customers now are the ones that we landed and that goes back to one.

[00:54:14] This is what happened at Grafana. I actually, landed a very large, software company in San Francisco. The guy we’re in the meeting and he says, everything you all are saying is sounds great. I’ve seen this time and a time again before I signed the deal and then I can’t get you on the phone. And I told him, I was like, okay, listen, I understand that.

[00:54:33] I’m telling you that if I commit to something, I will execute Beckley West Virginia, right there. Yes. 

[00:54:39] Chris Corcoran: Yeah, sure. Yeah. 

[00:54:40] Marc Gonyea: This is an honor. I’m serious. West Coast, they’ll buy into that 

[00:54:42] Chris Corcoran: stuff. Yeah. 

[00:54:43] James Holt: So, okay. Signs the deal. Good little land deal. this is three or four months into the implementation. I had not seen my parents in a long time.

[00:54:52] It was like six, seven months, eight months a year or something. They’re in Austin. We’re at dinner. I get a call this Friday night, 7:00 PM and it’s the guy I told him, I’ll execute what I say I will. And he says, I’ve got a major issue and it’s affecting a ton of revenue for this company. It cannot wait.

[00:55:09] You, I need help right now. You, I need you to get your people. They’re not answering fast enough. And so I left the dinner to go outside for two hours. Yeah. To talk on a cell phone, resolved everything, got it over. And then, you know, now they’re one of, they’re one of their very strategic customers. Um, he did two or three deals with me after that.

[00:55:29] They were, of magnitude Yeah. Larger because you built that trust. Yes. Like I told you, I would execute on what we did. And so it worked out very well. My family was not very happy. Yeah. Your mom’s so upset. Yeah. Yeah, right. Very upset by that. But you know, that’s, that’s part of the gig, I guess.

[00:55:43] Chris Corcoran: Alright. Pros and cons of the job. Yeah. Yeah. Pros and cons. 

[00:55:48] Marc Gonyea: So, you were there for I know, three years. Yeah, just over three years. Just over three years. How are you evaluating like the marketing, because in you With a cockroach. Yeah. Right. That’s, 

[00:55:59] Chris Corcoran: I’m saying 

[00:55:59] James Holt: that name. Yeah. Well, it gets a visceral reaction from people.

[00:56:02] When you say 

[00:56:03] Chris Corcoran: cockroach, do 

[00:56:03] Marc Gonyea: it, does I keep thinking of the biggest cockroach you’ve ever seen. Yeah. Costa Rica was ginormous. how do you evaluate like the next opportunity? Yeah. Because you were there. Well, I’m sure you could have kept hung around there. Mm-hmm. As long as you wanted, wanted.

[00:56:17] You’re probably welcomed. Like how, how do you, someone like you who, and you’ve obviously earned your badge as like a legitimate enterprise, so strategic accounts, whatever you wanna say, rep. How do you evaluate where you go next? 

[00:56:31] James Holt: Yeah. Yes. Question and And 

[00:56:33] Chris Corcoran: when 

[00:56:33] James Holt: to leave. Yeah, when to leave. So I look at my besting schedule, right?

[00:56:38] Yeah. Because if you’re gonna do pre-series or pre i p o tech companies, I go for the equity. Right. You can, you make good money on your w2, you get rich off your equity. Yep. if you choose the right company, very hard to do. Yes, 

[00:56:49] Chris Corcoran: it 

[00:56:49] Marc Gonyea: is. Especially in the sales, 

[00:56:50] James Holt: sales role. Yeah, exactly. But you can, there are ways you can, you can sniff it out.

[00:56:54] Tell us. Yeah, yeah. So there’s still whole for us, Chris. So, so I moved to New York actually for personal life. This is the first time I’ve moved for personal reasons. Yes. My girlfriends from the New York area, I had no family ties to Texas. Mm-hmm. after two years, especially post pandemic of flying back and forth and living a relationship out of a suitcase.

[00:57:10] It was, yep. Are we gonna continue to do this or are you, since you sell to the banks, Gwen, to just moved to the city you should be working in anyway, so Yes. Here, I’m 

[00:57:17] Chris Corcoran: you’re, 

[00:57:18] James Holt: yeah. Very logical. Yeah. Right. So, fair enough. That’s a hard argument. Objection to overcome. Um, she’s good at her job. Yeah. Yeah, exactly.

[00:57:25] Yeah. so I’m up here. you know, looking around, I’d finished my vest at Grafana. and I’m looking through and I typically, I personally like to take the riskier bat and go with a pre-series a, series a, series B max startup. But as you mentioned, right, the market really started to take a hit and, uh mm-hmm.

[00:57:42] As I was looking for my next role, I said I could go somewhere. I was in management for a long time at Grafana the last two years of it. Yep, yep. two years, something like that. Year and a half. you know, I had a couple offers for VP role, at two companies. I didn’t like their tech as much, but my time at Grafana, actually, I won, I was the account executive.

[00:58:02] You know, when we were managing, I can say this publicly, JP Morgan, gave Grafana Labs what they call their innovation award. And every, every year they give it to one to three tech companies that they say strategically and fundamentally changed the way the bank does business. And so for Grafana, you know, we allowed them through the visualization tool, to keep their servers up and their trading systems up while the crash and panic of COVID was happening.

[00:58:28] Oh. And because we were able to help them identify before servers were crashing, get them back up and keep their trading systems flowing, they had record revenue that quarter, right? So we win their innovation award. I was the rep that covered the deal, so we win that. The reason I bring that up is they give you a trophy.

[00:58:43] They shipped the trophy to me and it’s a guy named Eric Goldstein, my trophy for Cockroach Labs. And I was like, what is this? And they sent mine to him. Oh, no way. Didn’t think anything about it, right? Two years we switched it back, didn’t think anything of it. I’m interviewing for these jobs and a guy I worked with at Grafana said, Hey, You know, there’s this guy that I used to work for, I tick a bullet for me.

[00:59:03] He’s great, dude, you should, you should really hear him out. And he’s only got an IC role if that’s something you’re open to. And I was like, well, I’ve got these two offers for VPs. I don’t know if I wanna go back into carrying a bag, but I’ll hear him out. And so I met with him and I was like, this name is so familiar.

[00:59:17] And he and I started talking and he said, well, you know, we won JP Morgan’s Innovation Award in 2020. And I was like, you, I remember you. You are the rep. He was the rep that was covering. That won it and our trades got shit. So I was like, okay, one, if you won JP Morgan’s innovation award, that means the tech’s real.

[00:59:32] It works. Yeah. Yeah. 

[00:59:33] Chris Corcoran: Right. Yeah, yeah, yeah. Checkbox number one, what I 

[00:59:36] James Holt: look for. Yeah. Yeah. and two, right. You and I just hit it off, so great. You’ve carried a bag for 30 years. You’re not some sales manager that doesn’t know Yeah. Hasn’t sold anything for 20 years. Right? Yeah. You know, like 

[00:59:47] Chris Corcoran: first 

[00:59:47] James Holt: I love those guys.

[00:59:48] Oh, yeah, yeah. This is how I did it in 2004. Right, right. You know, the stories I tell nothing wrong with that, but maybe not 

[00:59:55] Chris Corcoran: frontline management, you know, but, that’s hysterical. Yeah. Yeah. So not 

[01:00:00] Marc Gonyea: frontline manager. 

[01:00:03] James Holt: James’s hysterical. But yeah, so we hit it off and, you know, decided to, to make the move over to Cockroach.

[01:00:08] but yeah, in, in terms of what I really look for, looking at a company, one, the tech has to be solid. Yeah. I don’t care that you landed customers. How many times have they expanded with you? What’s your net dollar retention? I mean, that’s what the VCs are looking at, right? Yeah. I mean, you look at Snowflake the greatest of all time.

[01:00:24] Yeah. For net dollar retention, right? Yeah. Look at that stock price. If you don’t have that Net dollar net retention. Net dollar retention. Yeah. Right. So when you think of like, from what I understand, like really top four, top five of all time, VMware, snowflake, ADE b Grafana is up there now. Yeah. so like you’re talking about, there’s a difference you can feel Yeah.

[01:00:42] When you’re working at those kinds of companies. Yeah. And so look at your net dollar retention. Make sure that if you’re evaluating a company, if you’re in it for the equity and that earning potential, obviously make sure that they’re landing customers, but then expanding within, you know, call that whatever your sales cycle is, but realistically within the next 12 months, they’re doing big more and bigger deals with you and more frequent and in different divisions because that’s how you know, if you can’t do that, you’re not gonna be successful.

[01:01:09] The company’s not gonna be successful. That’s the one I really look for. Right. The second one I always evaluate on is, really how do you like your direct manager that it is very important. Now things change in sales, you move different teams, so it’s not always the best barometer cuz things can happen.

[01:01:25] But like, can you see yourself working for this person? Because I think we’ve probably all worked at companies, right? Where maybe it’s a great product, maybe, you know, it’s a good company, but your manager really kind of dictates how miserable your life is, right? Absolutely. and also your manager, if they’re competent right?

[01:01:40] You, they’re gonna get promoted, you’re gonna be able to have opportunities to grow all that other, that’s right. That’s right. So technology number one, who you’re reporting to, number two. And then realistically, yeah. Number three, like what are we talking about comp wise? And so the trade off that you make, right, that I made here is like, okay, I’m Le Grafana, let’s do another pre-series A, let’s get just a, a ton of equity again.

[01:02:02] But looking at the funding in the VC environment, you know, over the past 18 months. Right. I was like, maybe it’s time to be more conservative than I normally would be. Yeah. See how this plays out. Right? Yeah. And so Cockroach had been already Series F. Yeah. Right. Raised 700, 600 million. so hey, we’re funded.

[01:02:19] We’re gonna make it through this downturn. Right? Yeah. Good product. We’ll go there. you know, and that’s kind of how I evaluate 

[01:02:24] Marc Gonyea: stuff. Yeah. But, yeah, no, that’s incredibly insightful. made a lot of good picks. memoryBlue SDR are thinking about, is my base 10 K higher? I’m in. Yeah. No, you know.

[01:02:33] Like, yeah, no. Yeah. You have to ask question. They don’t even care about the tech. They don’t even care about 

[01:02:37] Chris Corcoran: the tech. 

[01:02:38] James Holt: You should care about the tech. Your life is gonna be much simpler if you work for a company that’s, tech is not vaporware, right? 

[01:02:43] Marc Gonyea: Yeah. Well, I mean, if you, what kind of company has not, what’s it called again?

[01:02:47] Net. Net dollar retention. Net dollar retention. Yeah. The culture. It permeates the culture. Oh yeah. If they have happy customers who are coming back, they can focus their energies and their creative juices on making it better. Yeah. Or making their customer experience better versus like having to retain implementations that are going south.

[01:03:03] Yeah. And things that doesn’t, don’t work. It’s just a, 

[01:03:07] Chris Corcoran: it’s yeah. 

[01:03:08] James Holt: It’s, it’s contagious, right? Yeah. Your customer’s happy, they’re buying more. That means the company’s making money, the reps are making money, people are excited. You know, it’s a whole kind of, that’s why I think Mongo just did so well is because they created that culture of just like where

[01:03:20] the product’s great. People are making tons of money. We’re reinvesting. We’re only bringing the best people in. We’re saying no to 80% of the candidates. Yeah. You know, that are coming. It’s so hard to get in here. It made you want to do that much better. Yeah. Cuz you’re looking to the left and right of you and you’re like, you know, my first day again, I walked in or that crypto trading for, I was like, that felt like the first day of memory blue.

[01:03:39] I was like, I’ve made a terrible decision. These people are much, much more capable than I am. Right. 

[01:03:44] Chris Corcoran: that’s why these CS so hard to compete with these companies. Yeah. Yeah. They got the best tech. They’ve got the best salespeople. Yeah. Right. Yeah. They 

[01:03:51] Marc Gonyea: can solve the, and 

[01:03:52] Chris Corcoran: and then a company that doesn’t have as good tech, they’re not having, the salespeople aren’t as good.

[01:03:57] How are you gonna compete? And 

[01:03:58] Marc Gonyea: the customers aren’t as happy. Right? Yeah. It’s all, it’s spirals. Yeah. And I think another good point for the SDRs is just you have to keep in mind who your boss is. You can have a, a bad boss at a good, great company and your life will be miserable. Yeah. And you might not produce, you might not get moved to that next role.

[01:04:15] You might not get the exposure at the right level that what you want. and it, it’s probably not worth working there. Yeah. But you gotta have a boss that is gonna hold you to a level of expectation, output, but also gonna support you and like someone you can envision yourself working with.

[01:04:29] James Holt: Well, I think really from an SDR perspective, which be super important, is. if you are wanting to go into enterprise field sales, whatever we call it, you know, you do have to have that kind of mindset of the marathon and not the sprint. And you really, it’s very critical when you make your move from an sdr, if you go to another sdr org or if you get a bump up and you can go to inside sales, is taking, like we said, not only the manager, but the growth potential there.

[01:04:56] Because what you will find is, is if your end goal is to be carrying a bag for enterprise sales, what you’re gonna find is maybe you get an offer to go be an inside sales rep, you finally get that closing position, but it’s bad tech, bad company, all that stuff. What’s gonna happen is you’re gonna get stuck in that cycle of, I just wasted a year here.

[01:05:12] building up my brand, my internal, you know, champions, my customers, this or that. And now there’s no path to the enterprise here. So your options are, you’re just gonna be stuck there and just hope that something finally breaks your way or you’re gonna have to go to another company and start that whole clock over again.

[01:05:29] Right. And not to say like, I’ve seen, there’s no right way to do it. Right? There’s some are luckier than others. but I would say from an SDRs perspective, make sure that if your end goal is to be an enterprise rep, really dive into how real that company is about promoting SDRs to inside sales, inside sales to enterprise.

[01:05:49] Because when you talk to recruiters, when you talk to companies, they’re gonna give you the same thing. We got great training. We’re totally promoting people after four quarters of hitting their number. Yeah, we definitely have a great pro career, pro progression. Then the next question you should always ask is, Okay.

[01:06:04] Give me the, how many people you’ve promoted in the past 12 months from SDR to inside sales and inside sales up. And if they can’t name them, that’s a huge red flag. Correct. You should know that right there. It’s marketing to get you in the door. They have no intention on promoting. They want 

[01:06:17] Marc Gonyea: you for your leads.

[01:06:18] Yeah, exactly. They really book the meetings. They’re gonna churn and burn you. Yes. Right. Or maybe they help and pray it’ll work out. But you might be the first person if you’re the hamster or the Guinea pig. Excuse me. Sorry. Hamsters. The Guinea pig. You need to like know that. Yeah. Going in. Yeah. The 

[01:06:33] Chris Corcoran: pioneer takes the arrows.

[01:06:34] Marc Gonyea: Yeah. Yeah. You don’t wanna do that earlier. Right. So James, as we wrap up, has been very insightful. Yeah. Amazing. Thank you. if you could go back to that first night before you started at memory Blue, knowing what you know now, what advice would you have for yourself? 

[01:06:50] James Holt: What advice, study the database that you’re about to go learn about tomorrow.

[01:06:54] If we have, yeah. Yeah. So, but really just. I was very impatient. I’m all, I’m just an impatient person in general. Yeah. And I had the eye on the money and so my goal when I came to memory blues, like, I’m gonna be an sdr. I’m gonna be an enterprise sales rep in 12 months. which was just looking back on it.

[01:07:14] Nonsense. Right. You know? But like, that was the goal I set out. And I was like, so that’s why I was taking the meetings in DC two and all that stuff. Like, I’m gonna make this happen. But as as difficult as it is and I I remember how impatient I was. Remember the marathon, not the sprint. Get your foundations.

[01:07:33] The thing to remember, especially if you’re going to be in startup world, You really never start, stop doing the SD R BDR function, right? You will always be generating your own leads. You will always be reaching out to folks. I have seen QBR where reps go in and say, well, I didn’t get any meanings on the books cuz my SDR didn’t provide anything.

[01:07:53] And I have never seen that go Well, you know, 

[01:07:57] Chris Corcoran: ever do that. You will you 

[01:07:58] Marc Gonyea: Yeah. Yeah. 

[01:07:59] James Holt: You should Is the wrong place. Yes. So the thing that you have to remember is the best sales reps you’re ever going to meet, the ones I’ve ever met, are still excellent at the SDR function. Even though they’ve been an inside or they’ve been an enterprise rep for 10, 5, 10, 20 years, they’re still hammering the phones themselves.

[01:08:15] They’re still sending their own emails, they’re still sending LinkedIn requests, they’re all doing that. And then just what the SDR brings them is just like icing on the cake, right? Accelerators. Yeah. Accelerators, right. You, you, you will always be feeding yourself. And so it’s not like, You are just doing this tenure is an sdr, and then all of a sudden, now you’re an insight sales rep or enterprise.

[01:08:33] You’re just gonna kick back, do demos, deals, stuff like that. That’s not how it works. Right. And so getting, honing your skills during this time when you don’t have your seven figure quotas attached to your head. Yeah. Right. Honing your skills, learning the best way to reach out and strike up conversations and build pipeline is critical to the longevity in your success in this industry.

[01:08:53] Chris Corcoran: Walk off. That’s a walk off. 

[01:08:57] Marc Gonyea: That’s a walk off man. Because they, they forget. Yeah, but no, they never know. Yeah. They forget. They, they think they’re never gonna be an SDR again. You’re, you’re gonna be doing other things, but you need to do that. So I don’t wanna say anything else. Yeah. James, man, thank you very much.

[01:09:10] This is amazing. 

[01:09:11] Chris Corcoran: Proud me, man. What, what? It’s a what? A what? A what a career thus far. I can’t wait to see 

[01:09:16] Marc Gonyea: it’s been that 

[01:09:17] Chris Corcoran: long. memoryBlue. Yeah, but it What a just rising star man. Amazing. Yeah. 

[01:09:23] James Holt: Well, I have a lot to thank for you guys, man. That was a great, I mean, the people I met at Memory Blue and some of that context I still have, man.

[01:09:29] Yeah. We still talk, I still talk to Wes. Yeah. With Scott. All 

[01:09:31] Chris Corcoran: of you know. It was a great time. Those two are doing well. Yeah, both of ’em are doing well. 

[01:09:35] James Holt: Wes over at Data Doc, man. They’re crushing it. Joey’s over there now 

[01:09:37] Chris Corcoran: too. Joey called me. Okay. Joey works. Joey Cohen. Yeah. He 

[01:09:40] James Holt: called. Yeah, Joey called three or four months ago.

[01:09:42] We chatted about Datadog. yep. They’re direct competitor Grafana. I took a lot of their, I took a lot of their deals, 

[01:09:50] Chris Corcoran: but it’s cool that you guys stay, stay, in contact. Oh, 

[01:09:53] James Holt: yeah. I mean, it’s, it is honestly incredible when I think about, like, I’ve, I’ve met a ton of great people at Mongo crushing it all across, but you know, when I look back on our cohort now, yeah.

[01:10:03] when you look, there’s some serious, honestly, serious players now that came from Memory Blue and the class, the group that I was in. 

[01:10:09] Chris Corcoran: Right. Yeah. Those doubt. Well, I appreciate you being a part of it. All right. Leading the way. Yeah. Very good. Thanks James. Yeah.