Episode 88: Reuben Hagen – The First Impression
Consider making prospecting a team sport. Asking for help, input, and ideas from seasoned colleagues throughout his outreach cadence upped Reuben Hagen’s confidence.
Now a Commercial Account Executive at Datadog, Reuben recommends learning from experienced pros and peers alike. Trial and error make up a large percentage of a sales education and you can’t be afraid to fail, seek advice, and modify your approach.
In this episode of Tech Sales is for Hustlers, Reuben talks about what makes someone a good closer, working in a small company vs. a large company, and best practices when engaging in a cybersecurity campaign.
Guest-At-A-Glance
💡 Name: Reuben Hagen
💡 What he does: Reuben is a commercial account executive at Datadog.
💡 Company: Datadog
💡 Noteworthy: Reuben worked as a camp counselor and a lifeguard for many years. In high school, he took many business classes, including accounting law, and later, he studied accounting as a major at UMass Amherst. However, he quickly realized that that was not what he wanted to do, and right out of college, Ruben started working at memoryBlue as an SDR. Today, he’s a commercial account executive at Datadog.
💡 Where to find Reuben: LinkedIn | Website
Key Insights
⚡ Soak up the knowledge of successful SDRs. Reuben took a job at memoryBlue as an SDR at the suggestion of his friend. Although it was unfamiliar terrain for him, he observed the successful SDRs around him and absorbed their knowledge. “People do different things as an SDR that make them successful. There are multiple paths you can take. And so, I just found one that seemed to work really well for me; I found someone who’s really good at emailing and pulled some emails from them; I found someone who’s really good at calling people on the phone and discovered what made them successful. And then I just chose what worked well for me.”
⚡ Having a beginner and someone more experienced by your side is very useful. Reuben came to memoryBlue in February 2020, shortly before the start of the pandemic and the shift to remote work. But, as he points out, it meant a lot to him that, at the very beginning, he was surrounded by people who started with him as well as SDRs who’ve pushed through that beginning. “I think it’s really useful to have both of those. You have someone at the same time as you, who’s learning the same way, and who’s also starting with very little knowledge. And you two can just talk and figure out what’s going on and be like, ‘I don’t know this. Have you been able to learn this from someone?’ And also people who went through it, so they know what it’s like to start with that.”
⚡ The first impression on the phone is very important for an SDR. Working with clients as an SDR, Reuben first communicated with them by email and later switched to telephone communication. Based on his experience, he notes that the critical thing is to prepare well for the interview, learn all about the client, and get their attention right at the beginning of the interview. “The first impression was huge. If I called them, the first 10-15 seconds would often tell if we were going to get a meeting out of that or not and just how receptive they were to that. How I opened was really, really important; it was key. […] Your intention comes off so easily on the phone, even if they can’t see you and don’t know you. People pick up on that really quickly — your tone of voice and what questions you’re asking them.”
Episode Highlights
Small or Big Company?
“It’s great to have both experiences — being at a very small company where you have that big impact and a large one where you have a lot of people in the same role as you. The main challenge for me in the smaller companies was finding someone who was doing something similar to me, even if that meant talking to people outside of that company to see how it was going for them.
Then I went to AssuriCare. I was the first and the only SDR there. I’d check in with other SDRs all the time and talk with them on FaceTime and see what was going on. And that was really key for me because I was trying to figure stuff out and I wanted people to bounce that off of.”
Failing Is Not Bad
“You’re going to fail a ton of times as an SDR; you just have to be able to move on from it. And it’s not the end of the world. And it definitely felt like the end of the world at times, when I had a bad month or something, and I’d feel very horrible. But just being able to move on from that and take things slowly.
The job’s very important, and you end up generating a lot of revenue for these companies. But you can’t win every single one, and you’re not going to, and just not being hard on yourself after the ones that don’t work out, and finding those just relaxed with the job. It can be stressful at times, for sure. Just finding ways after you just got yelled at by someone, or you had a deal go sideways that you thought for sure was going to close — finding ways to lighten the mood is so key.”
What Makes a Good Manager?
“There are a lot of things and a lot of different ways you can go about it, but the best leaders that I’ve had are people that are able to personalize it for everyone they work with and not just one-size-fits-all: ‘Here’s my management structure, you’re all going to come in and work in that framework.’ Instead, they are able to adapt it to each person and see what they do well.
Just being able to identify what people are good at and what motivates them. Because I am motivated very differently from someone next to me — I might be less money-oriented or more time-oriented.
What Makes Someone a Good Closer?
“I think what makes a good closer is being able to relate to each person you work with really well and not trying to fit them into your selling structure, and instead, adapting to their buying structure and relating to them as a person. Yes, they’re an employee, and their role might be an engineering manager, but what’s actually important to them and figuring that out. And then being able to have a conversation with them rather than just saying, ‘What are you going to do for me?'”
Transcript:
[00:00:00] Rueben Hagen: I think there’s a lot of things and a lot of different ways you can go about it, but where I’ve seen the best leaders that I’ve had are people that are able to personalize it for everyone they work with and not just have, like, one-size-fits-all.
[00:00:36] Marc Gonyea: Reuben Hagen in the house. Hey man. Thanks for joining us.
[00:00:39] Rueben Hagen: Absolutely. Nice to be here.
[00:00:41] Chris Corcoran: Reuben, good seeing you again.
[00:00:44] Looking forward to catching up with you.
[00:00:46] Reuben Hagen: Yeah. You as well. Sounds good.
[00:00:47] Marc Gonyea: All right. Reuben, where are you today? So, we’re doing this remote. Chris and I are in, and you’re downtown?
[00:00:55] Rueben Hagen: Yeah, I’m in the Financial
[00:00:56] District in Boston, at the Datadog office, but I
[00:00:59] actually, I live in Walthamstow. I’ll be going back there later tonight.
[00:01:03] Marc Gonyea: Oh, are we going to have the pleasure of seeing you tomorrow at the open house?
[00:01:06] Rueben Hagen: Maybe. It’s my
[00:01:06] mom’s birthday tomorrow,
[00:01:08] so I might be going back to Western Mass
[00:01:10] Marc Gonyea: She’ll understand.
[00:01:16] Chris Corcoran: Reuben, let’s do this for myself, maybe less so for Chris, but for the audience, take us back, back, tell us a little bit about where you grew up, what were you like as a kid. We’ll kind of, it’s good for us to kind of get a feel for you and learn a little bit about your background.
[00:01:31] Rueben Hagen: Yeah, definitely. I grew up in Amherst in Western Massachusetts, was there for most of my life and went to UMass Amherst, so actually went to college closer to my parents’ house and where I went to high school.
[00:01:46] Marc Gonyea: Oh, no.
[00:01:47] Rueben Hagen: Still, yeah, pretty unusual experience there, but still lived in the dorms at UMass. I don’t think my parents wanted me to live at home or me wanting to go over there.
[00:01:58] So, went to master for years and then after that didn’t really know what I was going to be doing out of college and I had a good friend of mine that worked at memoryBlue, so talked to him about it and he was like, “Yeah, it’s a fun place to work. I like everyone I work with.” And so I started working at memoryBlue from right out of college at UMass.
[00:02:18] Marc Gonyea: Perfect. Let’s go back just a little bit though. Just that Western Mass like, a lot of people don’t even know that’s a place. So, like, it’s a college town, Amherst or what?
[00:02:28] Rueben Hagen: Amherst itself is a very much a college town. There’s five colleges, right in Amherst, in the area around there, but outside of that it’s mainly farmland. I think the town I grew up in had about 1200 people total just in elementary school, then there’s a regional high school in Amherst. So, very much out in the woods in Western Mass, I loved growing up.
[00:02:52] But very different experience now being in, like, downtown Boston, it’s kind of two different worlds.
[00:02:59] Marc Gonyea: Just to frame things up, how far of a drive is that from Boston to Western Mass, you know, Amherst or your town?
[00:03:05] Rueben Hagen: It’s just standard two hours,
[00:03:07] if
[00:03:07] you do it pretty quickly and don’t get pulled over along the way.
[00:03:11] Marc Gonyea: Okay. When you were growing up and what’d you do as a kid? Some people worked and we got jobs and we played sports. What was your thing?
[00:03:18] Rueben Hagen: Yeah, it was a mix of sports. I’m kind of just also playing around with my friends. And then I worked as a camp counselor and a lifeguard for many years. So, summers were spent lifeguarding. I could ride my bike from my parents’ house to the pool there and a lot of my good friends work there as well. So, life growing up was pretty,
[00:03:40] it was pretty nice. Can’t complain about
[00:03:42] it.
[00:03:43] Marc Gonyea: You earn to keep now as a tech sales professional. Did that, the promise of that grandiose career living in Boston, like, did that or wall of fame got working at Boston? Did that, like, come up as a kid? The idea of being in sales?
[00:03:58] Rueben Hagen: Not really, to be honest. I mean, still I, sometimes the city very much overwhelms
[00:04:03] me.
[00:04:05] I like kind of being out a little bit away from the city as much as I can, so I live in Wall Fan, which is a mix of city life land a little bit more suburban out of that. And so, growing up, I mean, I liked being out in Western Mass.
[00:04:21] I really liked it there. I liked having so much free space to kind of do what I
[00:04:25] want.
[00:04:26] And so I don’t think living in the city was near, like, a big attraction for me. It was just kind of where I thought I could develop most career-wise and learn the most. And then also just after finishing UMass, most of my friends lived around here,
[00:04:41] so I wanted to stay near the people I knew, kind of my network of, network of people to both hang out with outside of work and to work with, was what brought me to
[00:04:51] Boston.
[00:04:52] Chris Corcoran: When you were in high school, what did you want to be when you grew up, when you were in high school?
[00:04:57] Rueben Hagen: Honestly, I have no idea what I wanted to be in high school. I kind of was all over the place. I took a ton of business classes in high school, we had a great business teacher, and so I kind of took all of those. I took a bunch of, the main one they taught was accounting law and so I did Accounting as my major for at UMass, then
[00:05:18] from doing accounting for four years, realized that’s absolutely not what I wanted to do, was kind of what I learned through that, but I didn’t really have a direct thing I really wanted to
[00:05:28] do
[00:05:28] growing up.
[00:05:29] Chris Corcoran: So, you studied accounting at edu, at, at UMass?
[00:05:31] Rueben Hagen: Yeah. I studied accounting there and.
[00:05:34] Chris Corcoran: And what you learned was, “I don’t want to be in accounting?”
[00:05:36] Rueben Hagen: Yep, absolutely that. That was the main thing I learned, which is a great thing to learn, but I both, like I saw a lot of my friends from those classes get internships in accounting and then ones that were older started the careers in it. I was just like, “I don’t want to work 70 hours a week doing this. Like I want to have a work-life balance.”
[00:05:55] I very much enjoy having a life outside of work to do things. And that’s what drew me, I think, to tech as well, tech sales, is that I saw a lot of people who had a good work-life balance and were able to have a fun time. Like, maybe it was older coworkers hanging outside of work, but they weren’t always working.
[00:06:15] They were having a fun time
[00:06:16] with it too and that’s
[00:06:18] what drew me here along.
[00:06:19] Chris Corcoran: So, you must have had quite a conundrum on your hands, right? You just spent four years of your life and paid a lot of money to the Commonwealth of Massachusetts to earn a degree and a very sought-after skill, accounting, and I’m sure you had plenty of suitors who wanted to hire you to be an accountant, but that’s the last thing in the world you wanted to do.
[00:06:41] So, you had to turn down these opportunities for anything but being an accountant. And so how did you navigate that and what mom and dad say about this whole thing?
[00:06:51] Rueben Hagen: Yeah, definitely. My parents were very, are very supportive, luckily, of whatever I want to do. They weren’t, like, pushing me or being like, “Hey, you did this for four years. You don’t have to do it.” Both of them are actually, they work in biology at UMass. My dad’s a professor and works in labs, and so they didn’t push me to be in science, biology.
[00:07:12] Once I was done with accounting, they didn’t really push me to do that. And so it was kind of just talking to people I knew seeing what their life was like. I still have a bunch of a friends from UMass who are still in the accounting and so I’m able to talk with them, see what they liked, didn’t like about it and then talk with other friends and see what they kind of like, what they like, how it’s going and made my decision from there.
[00:07:34] Chris Corcoran: And so then, how did you find tech sales? ‘Cause the, the one, the nice thing about, uh, I would say about a technical degree, an accounting degree, is that transmits a signal that you’re smart and that you also could pay attention to details, which those are critical skills in lots of different professions, critically tech sale, or especially tech sale,
[00:07:55] so how did you find your way into this profession?
[00:07:58] Rueben Hagen: Yeah, it was through one of my good friends growing up in Amherst, worked at memoryBlue and so it was very much a just kind of network of we were hanging out during the summer and he mentioned it to me and I was like, “Yeah, I don’t want to do accounting. I’m open to exploring options” and went from there.
[00:08:16] And that’s how even after memoryBlue most of my jobs have came about, is people I know who are like, “I really like working here. I think it’s a good opportunity.” And I’m like, “Yeah, that sounds interesting. I’d be open
[00:08:28] to
[00:08:28] exploring it.”
[00:08:29] Chris Corcoran: So, that conversation, that happened the summer after you graduated?
[00:08:33] Rueben Hagen: Yeah, I graduated a semester late, so I graduated in the fall and then it happened, I graduated in December and by the middle of January, I talked to, interviewed with my blow a few times and decided to come here. It was pretty bang, bang, and I feel very lucky because that was a right before COVID started
[00:08:54] and if I had waited a month later,
[00:08:57] I
[00:08:57] would maybe still be stuck
[00:08:59] in
[00:08:59] Amherst.
[00:09:00] Chris Corcoran: Wow. Timing’s everything. So, you started, when did you start? February?
[00:09:04] Rueben Hagen: Yeah. I started, like, February
[00:09:05] 4th,
[00:09:06] I
[00:09:06] think.
[00:09:06] Chris Corcoran: Of 2020?
[00:09:08] Rueben Hagen: Yeah. So, I graduated in December, lived at my parents’ in January and was like, “I want to get out of here as quick as I can,” to be able to sign a lease February, it was perfect time and worked out
[00:09:19] really well.
[00:09:20] Chris Corcoran: That’s great. Very good. So, very rarely in life are your experiences exactly what your expectations are. So, talk to us a little bit about just the, the SDR job in terms of what you expected and how it actually was different than what you expected, even though you had an insider, right? You had a friend who had worked here
[00:09:41] did he kind of give you the inside scoop, but how was it different than what you thought it was going to be?
[00:09:46] Rueben Hagen: Yeah. I really went into it with very little expectations of what it would be like, other than my friend talking to me. I
[00:09:53] think
[00:09:54] one big thing was it wasn’t as much, like, very detailed research as I thought. I thought would be a lot
[00:10:00] more
[00:10:01] like research, maybe more inbound stuff, but I, to be honest with you, it didn’t have much expectations at all going into it.
[00:10:08] And a lot of it was just learning on the fly, learning from other people who had been successful as an SDR there and seeing what, like, made them successful and then
[00:10:17] trying
[00:10:18] my best to replicate it. Because
[00:10:20] I
[00:10:20] think
[00:10:21] as
[00:10:21] people do so many different things as an SDR that makes them successful and there’s multiple kinds of paths you can take.
[00:10:28] And so I kind of just found one that seemed to work really well for me. I found, like, someone who’s really good at e-mailing, pulled some emails from them and found someone who’s really good at calling people on the phone and what made them successful and then just kind of chose what worked well
[00:10:43] for me.
[00:10:44] Chris Corcoran: Very good. So, you would just find a, kind of the best player at each position and then try to model your game after his or hers?
[00:10:50] Rueben Hagen: Yeah, exactly. That’s what I’ve done since then. I think that’s, especially, like, for my learning style, that’s how it works best. Just find someone
[00:10:57] who’s good at it, who’s proven to be successful and copy what they’re doing
[00:11:02] Chris Corcoran: Yeah. So, essentially, what you can get expelled from college to do is copying everything, right?
[00:11:07] Rueben Hagen: Exactly. Just
[00:11:08] caught
[00:11:09] in
[00:11:09] college,
[00:11:09] in there.
[00:11:10] So, who, whose game did you model? Like, when you were here, who was, “Oh, man, this person’s an unbelievable emailer” or, “This person on the phone is smooth as silk.”
[00:11:20] Rueben Hagen: Yeah, there was someone named Sean when I started really good emails, kind of copied him and then for calls, really,
she was after, like, a week, my manager, Ellie, took everything she did. It
[00:11:32] was awesome.
[00:11:33] Chris Corcoran: So, you copied Ellie?
[00:11:35]
[00:11:35] Rueben Hagen: Yeah.
[00:11:35] I, most of my tips came right from her.
[00:11:38] Talk about how it was learning ’cause you started in, in February of 2020 and then a month and a half later it was work from home. Although it sounds to me like you had a little memoryBlue office going a two man, {…} to memoryBlue office in Waltham.
[00:11:53] Rueben Hagen: Yeah, I think I was very fortunate to be able to be in person to start. I’ve found it way easier to learn
[00:12:00] when
[00:12:00] you
[00:12:00] have
[00:12:01] someone next to you who’s starting at the same time as you and then people next to you who have been through it. Whether those a few months earlier, a year earlier, I think it’s really useful that both of those. You have someone at the same time as you,
[00:12:13] who’s learning the same way, who, like,
[00:12:15] also
[00:12:17] starting with very little knowledge and you two can just like talk and figure out what’s going on and be like, “I don’t know this. Have you been able to learn this from
[00:12:24] someone?”
[00:12:25] and then also if people
[00:12:26] have went
[00:12:27] through it
[00:12:27] and recently, so they kind of know what it’s like to start with that.
[00:12:32] And then once we went remote, I was still, because I developed those relationships already with them, was really easy to FaceTime them and be like, “Hey, I don’t know what’s going on here. Like, I got this question on the phone. I have no idea how to answer it. Like, how do you come
[00:12:44] across
[00:12:44] Reuben Hagen: that?”
[00:12:45] Marc Gonyea: What did you get good at, Reuben, specifically? Like, what was your, your move?
[00:12:49] Rueben Hagen: My move to s, I think it’s kind of evolved over time. It started off very much being e-mail-driven. My first client was in Europe and so it was really hard to get phone numbers for them and it was very, very
[00:13:00] much
[00:13:01] email-oriented. And then when it moved to my next client, I kind of started off, I was like, “That’s my bread and butter.
[00:13:07] I know how to do that well.” But then it was like a home care client and so I had to adapt because
[00:13:13] most
[00:13:13] of them
[00:13:14] are older, retired nurses, don’t check their emails, there’s like one email for the entire company. That’s not a good way to get in touch and so it had to evolve very quickly to being over the phone
[00:13:26] and that was all about, like, the first impression was huge. If I called them, that first impression, the first 10, 15
[00:13:34] seconds,
[00:13:35] I often would know if we were going to get a meeting out of that or not and just how they’re receptive to that.
[00:13:39] And
[00:13:39] so I think
[00:13:40] how I opened was really, really important and just how
[00:13:44] I
[00:13:44] said, like,
[00:13:45] I
[00:13:46] was
[00:13:46] key.
[00:13:47] Marc Gonyea: How’d you get good at that? Did you, like, how did that awareness grow? From doing it or for something else?
[00:13:54] Rueben Hagen: Yeah, I think the main way is just doing it over and over getting those repetitions and, I mean, I could do role-plays all I wanted, practices all I wanted,
[00:14:03] but
[00:14:04] until you’re on the phones and actually talking to people, it’s hard to really get that experience and to really
[00:14:09] be, like,
[00:14:10] panic when someone asks you a question, you don’t know how to answer and then you’re definitely going to go figure that out after that
[00:14:16] when you have someone
[00:14:17] on the phone
[00:14:18] and I think just doing it over and over
[00:14:20] Rueben Hagen: was
[00:14:20] how
[00:14:20] I
[00:14:20] learned.
[00:14:21] Chris Corcoran: Well, so, Reuben, I know you’ll find this hard to believe, but not everybody goes effort, they are asked a question that they don’t, don’t know the answer, not everybody goes and finds out the answer to the question. So, kudos to you for having that curiosity so that the next time you’re asked the question, you have an answer and that’s how you grow.
[00:14:38] That was up to you.
[00:14:40] Rueben Hagen: Yeah. And I think, I owe also a lot of credit to, like, the team I had around me. I mean, that was very much the culture on the team I had, was everyone asked those questions and if I hadn’t been on a team like that, I
[00:14:54] don’t know if I
[00:14:55] would. And so, I think a lot of credit goes to people who had been there before me and got that culture going of
[00:15:02] ask as many questions you can, when something comes up you don’t know.
[00:15:06] Because we were all doing it and even the people who had been there for a long time still ask questions and sometimes someone who’s brand new might know that answer. And so I think a lot of credit just goes to the culture of the people
[00:15:20] Reuben Hagen: around me?
[00:15:20] Marc Gonyea: When you were at memoryBlue, so, you know, you’re new to sales, you’ve put, in the county background, you had friends in sales. How did your perspective on the profession evolve when you were doing the SDR job?
[00:15:34] Rueben Hagen: Yeah,
[00:15:34] I think it evolves in that I got more personalized in talking to people. I think
[00:15:44] as I would get more comfortable with the client and each persona was reaching out to, I was able to kind of know what pain they might have before going into that and be much more targeted rather than starting
[00:15:57] out, you have to be pretty general.
[00:15:59] Like, I think it also helps too, because you’re so curious, so you don’t
[00:16:03] know
[00:16:04] what you don’t know and you would ask so many questions because you were just trying to figure
[00:16:08] it
[00:16:08] out yourself.
[00:16:09] Over time I think I was able to get more personalized ’cause I’d
[00:16:13] be
[00:16:13] like,
[00:16:13] “All right,
[00:16:14] I’ve worked with someone in a pretty sit, similar situation as this person.
[00:16:19] How can I kind of relate it to them?” And having those proof points of being like, “I’ve worked with someone like this before. I know what the process is like,”
[00:16:27] because they might buy software once every few years, like, at most, all the time and I’m selling people every day and so just getting familiar with that process has definitely
[00:16:38] evolved how I go about conversations.
[00:16:41] Marc Gonyea: And you know what? We’ll get to this, but, you know, you’ve had, you’ve been a leader since leaving memoryBlue and now you’re closer. Has that stuck with you in terms of how you bring that to these other positions?
[00:16:52] Rueben Hagen: Yeah, definitely. I think most of the skills I had as
[00:16:56] an SDR
[00:16:57] has stuck with me. I still, like, in a closing role, spend most
[00:17:01] of my day prospecting, I mean, that building up pipeline is key.
[00:17:06] And so none of those skills in any way go away, you just have to learn how to become really efficient with them. Because where you might have 8 hours as an SDR to spend prospecting, you
[00:17:17] now, all of a sudden, we’ll have
[00:17:18] to fit that in 2 hours. And so, learning to
[00:17:21] become really efficient with that plan really well, so that when you are, like, out there executing, you know what you’re doing
[00:17:29] and you don’t have to try to come up
[00:17:30] Reuben Hagen: with it on point.
[00:17:31] Marc Gonyea: Yeah. What about the profession uh, where you want to take your career path? Did you get in and say, “Okay, this SDR job, I kind of knew what I was but wasn’t sure.” Did you say, “Oh shoot. I want to be a then be a closer. I want to to do something else,” you know, ’cause it’s only natural the
[00:17:49] way we operate the model here, is you can go for, for your client, we’ll get to with you in a sec, but I’m super curious about someone with accounting background, how you looked at, where you wanted take your journey after the SDR role. Once you got into the SDR role sort doing it and working with clients and seeing people leave, you know, give them more exposed to alumni in the office, people are going to promote it
[00:18:08] Marc Gonyea: internal.
[00:18:09] Rueben Hagen: Yeah, I think my thinking about it was just to keep as many doors as possible open. I never want to draw any of those, whether it’s moving up market to becoming an enterprise rep
[00:18:22] or being
[00:18:22] in, like, a team lead manager role, I want to keep
[00:18:26] all those doors open and explore them as much as possible, so just talking to people who are in
[00:18:31] those
[00:18:31] roles,
[00:18:32] seeing what they like, pros and cons of why they chose to go that way.
[00:18:38]
[00:18:38] Rueben Hagen: And I, at this point, I’m still very open to any role, like, moving forward. I don’t have a concrete path of like, “I want to be an enterprise rep with,
[00:18:47] uh,
[00:18:48] closing million-dollar deals, or I want
[00:18:50] to
[00:18:51] be a VP of sales.” I’m keeping, like, just as many doors as possible open
[00:18:57] and
[00:18:57] see what’s out there.
[00:18:59] Marc Gonyea: So, when you’re working with your client, I mean, they came to you in fairly short order. I mean, you had, as the model allows, you worked with us for I would say all too long of a time.
[00:19:09] So, talk, talk about some of the experience, you getting converted and what your thought process going into that and so on.
[00:19:15] Rueben Hagen: Yeah. So, the client I ended up getting hired out by
[00:19:17] was
[00:19:17] my second
[00:19:18] client. I had the first one
[00:19:19] for roughly
[00:19:20] two or three months
[00:19:21] and then the second client AssuriCare, was hired out by them after, like, five months
[00:19:27] working with them.
[00:19:28] And I think why that
[00:19:30] came about
[00:19:30] was, I mean, they just, their sales organization was the VP
[00:19:34] of
[00:19:34] sales
[00:19:35] and then me. Like,
[00:19:36] it was the two of us.
[00:19:37] And
[00:19:37] so
[00:19:37] we got to know each other really, really well and that’s definitely what facilitated, being hired out so quickly, is that I, we just had a really close relationship. We worked really
[00:19:47] well
[00:19:48] together. We were in pretty much constant communication every day
[00:19:53] about what I was hearing, what he was hearing. He was doing cold calls too, like, he was doing the same things I was as well, but then also closing. So, he knew what it
[00:20:04] was like
[00:20:05] cold calling into the companies
[00:20:07] we were
[00:20:08] and we were able to kind of figure things out together. And so that’s
[00:20:12] definitely
[00:20:13] what made that move forward as quickly as it did, is just constant communication and
[00:20:18] building
[00:20:18] that
[00:20:19] relationship up.
[00:20:20] Marc Gonyea: So, you’re saying to the relationship you have with the client was pivotal and you decided to exit memoryBlue and go work for the client directly?
[00:20:28] Rueben Hagen: Yeah. Definitely. I went back and forth. I was right on the fence of whether to go there or stay in memoryBlue. And I had multiple conversations with Jeremy, with Ellie about pros and cons of each. And definitely the reason I ended up deciding to do that was because of my relationship with the VP of sales there.
[00:20:47] And I knew I wasn’t going to go there and any get screwed over, like, I very much trusted him and liked working
[00:20:54] with him and
[00:20:55] saw
[00:20:56] a
[00:20:57] path
[00:20:57] forward there. I was like their first sales hire other than the
[00:21:00] VP of sales to bring in, like, tools like ZoomInfo.
[00:21:06] They used HubSpot at the time and got Salesforce as well to start building that sales team
[00:21:12] Reuben Hagen: there.
[00:21:13] Chris Corcoran: What was that transition like? Like, what was it like working for the client directly and go order from memoryBlue?
[00:21:18] It was finding ways to keep myself accountable because
[00:21:22] Rueben Hagen: there’s
[00:21:23] all of a sudden, no kind of restraints on
[00:21:26] that and I had
[00:21:27] full independence to do what I want every day. And so setting up ways of being like, “Hey Scott, like, checkup
[00:21:34] with me
[00:21:35] on these days. Here’s what I wanted to get done, make sure I got this done.” Because if I don’t set those up, I don’t
[00:21:44] think I’d have gotten them done and so just finding ways to, like, get someone else other than you to keep you accountable to your goals.
[00:21:52] Chris Corcoran: The accountability partner.
[00:21:54] Rueben Hagen: Yeah.
[00:21:55] That was key.
[00:21:56] Like,
[00:21:57] I
[00:21:57] think in college too, like, if someone gave me homework to do, there’s a decent chance that homework wasn’t getting done, but if I was on a group project with
[00:22:04] four
[00:22:04] other
[00:22:05] people,
[00:22:06] I’d get it done because I’d want to be, get my part done for those other people.
[00:22:09] But if it’s just for myself, that’s much
[00:22:11] harder,
[00:22:12] I think, to keep yourself in check. So, and I’ve applied that to a lot of areas, like, find friends and people to be like, “All right, I want to be here. Like, how can I get there? And then, like, what points along the way do I want to crack on with someone
[00:22:27] else to make sure I got there?”
[00:22:28] Marc Gonyea: What was it, like, working at a company where, you know, you’re working at a large company now, I think what I, you know, checking on your background, what you’ve done and we’ll talk about the next thing, you went from memoryBlue, which is not a super small company, but not that large and then working for your client, small business,
[00:22:46] right? And then now you work at a company with thousands of people. I mean, low thousands, but much larger in size. What was that like? In terms of, Chris likes to say you can have a huge impact on a business that way when you’re, like, the only person really dedicated, exclusively to building the funnel.
[00:23:04] Rueben Hagen: Yeah, I, it’s very different and I think it’s great to have both experiences while being at a very small company where you do have that big impact and a large one where you have a lot
[00:23:14] of people
[00:23:16] in the same role as you. And I think the main challenge for me of the smaller companies was finding someone who is doing something similar as me, even if that meant, like, talking to people outside of that company,
[00:23:29] to see how it was going for them. And, like,
[00:23:32] I still want to and went to AssuriCare,
[00:23:34] I
[00:23:34] was the
[00:23:35] first, only SDR there. I check in with other SDRs all the time and talk with them
[00:23:40] or FaceTime
[00:23:40] them, see what was going on and that was really key for me
[00:23:44] kind
[00:23:44] of,
[00:23:45] because I didn’t know what, I was trying to figure stuff out as I went, I wanted people to bounce that off
[00:23:50] Reuben Hagen: of.
[00:23:51] Chris Corcoran: Of course. Eventually you made a decision to move on. What was the thought process in the moving into the next thing, to go to ReversingLabs?
[00:25:01] Rueben Hagen: Yeah, that was mainly, I was really excited to go into cybersecurity.
[00:25:05] I, that was something that really
[00:25:08] interests me.
[00:25:09] And then same with joining memoryBlue. I, there were three other people that
[00:25:13] I
[00:25:13] knew
[00:25:13] there from
[00:25:14] memoryBlue
[00:25:14] who really liked it. They really liked their boss. And so I, I mean, I
[00:25:19] talked to them all the, I still talk to them all the time
[00:25:22]
[00:25:22] Rueben Hagen: and
[00:25:23] just
[00:25:24] getting into cybersecurity and then working with a team again, I really liked having 18 to work with and not just being, like, an individual contributor, was a big motivating factor and then cybersecurity is just very
[00:25:36] interesting to me.
[00:25:37] Marc Gonyea: Why is that? Because, I mean, I’m going to speak {…}, I have my opinion, I agree with you, but we have folks who are working at memoryBlue and who, there’s a taste off the cyber. Cyber is really difficult, it’s really hard, but, I mean, you were coming from complete non-cyber in the cyber and you were excited about it.
[00:25:56] So, why were you excited about it and what, what would you tell an SDR who’s elected to engage in a cyber campaign?
[00:26:02] Rueben Hagen: I kinda just, I wanted the challenge
[00:26:05] of working with
[00:26:06] people who are quote-unquote, like, harder to get in touch with and I don’t think
[00:26:11] that’s really true that they’re often, like, harder clients to work with. I think it’s just different in how you
[00:26:17] get with them, how you get to talk to them. I mean, most
[00:26:20] cybersecurity engineers and
[00:26:21] architects are very direct and to the point and so you
[00:26:25] just need to communicate in that style with them. There’s no, like, fluff needed. They’re just like, “Why are you going to be useful to me? Why am I going to take time to talk with you?” And then once you’ve proven that they open up a lot more.
[00:26:37] And then I think the other thing I really liked about cyber security is I was always someone who didn’t mind like taking test
[00:26:44] as a kid growing up. I didn’t like essays, I didn’t like homework, behind
[00:26:48] mind tasks.
[00:26:49] And so, cybersecurity, there’s a ton of certifications in the field that you can go and get as, like, anyone and that was very exciting to me, to being able to like, I can level up my career by
[00:26:59] going to, getting these certifications and they carry a lot of weight, like,
[00:27:05] they’re difficult, yeah, but then people see them on your LinkedIn and they’ll have a conversation with you much quicker
[00:27:10] ’cause it’s just
[00:27:10] instant credibility there.
[00:27:12] Marc Gonyea: And you seem to have some patience, which is good, because I think you put some thought into these things, going to work for your client, going to ReversingLabs, talking with people who are already in the role. Sometimes folks will, “I want to be a closer. I want to be a closer. I want to be a closer” and it’ll take a job closing at a company that they, you know,
[00:27:35] really, really risky. You were an SDR, then you were a team lead or senior SDR, then a team lead, walk us through that kind of process where you at this point, “Hey, I want to be a closer, but I’m kind of slow playing it” or were you, “I’m more interested in cyber and the other stuff will come.”
[00:27:49] I was never really in a rush to be in a closing role. I kind of just saw it as it will
[00:27:55] Rueben Hagen: come, like,
[00:27:56] when it
[00:27:56] comes, but I was just kind of
[00:27:59] there
[00:27:59] to
[00:28:01] learn as much as I could in that
[00:28:03] position
[00:28:04] and be very well set up for whatever was next,
[00:28:08] whether
[00:28:08] it was
[00:28:09] like
[00:28:09] fully just
[00:28:10] managing
[00:28:10] an
[00:28:10] SDR
[00:28:11] team and not going into closing role or being in a closing role.
[00:28:15] I just wanted to keep the doors
[00:28:17] open.
[00:28:18] There never really was a rush
[00:28:20] Rueben Hagen: to
[00:28:20] move into that
[00:28:21] closing role because I knew there were a ton of options out there
[00:28:25] for
[00:28:26] paths to go and I wasn’t set on any one thing and so I was never trying
[00:28:31] to, like,
[00:28:32] get
[00:28:32] there as
[00:28:32] quickly
[00:28:32] as I
[00:28:33] could.
[00:28:34] Where do you think that comes from? ‘Cause not a lot of people have that perspective.
[00:28:37] Rueben Hagen: I’m
[00:28:38] not
[00:28:38] really that sure.
[00:28:40] I
[00:28:41] think
[00:28:42] I
[00:28:42] would,
[00:28:42] I don’t know, there was there’s challenges in any position you’re in, no matter what and
[00:28:47] so
[00:28:48] they’re going to be different in a closing role than they are as an
[00:28:51] SDR,
[00:28:52] but
[00:28:52] you, like, you have to be a good SDR,
[00:28:55] I
[00:28:55] think, to be
[00:28:55] a
[00:28:55] good
[00:28:56] AE.
[00:28:56] Like,
[00:28:57]
[00:28:57] Rueben Hagen: maybe there’s some
rules out there and you’re not doing any prospect, but I find like I’m doing prospecting myself. I have an SDR
[00:29:04] that supports me, but I’m still doing a ton of prospecting myself and I learned how
[00:29:10] to
[00:29:11] be very, very efficient with that. And I could get comparable activity than someone who worked eight hours a day in, like, an hour and a half and two hours. And so, I
[00:29:19] would
[00:29:19] just, as
[00:29:20] an
[00:29:21] SDR, got, like, pretty ruthlessly efficient with how I prospected and being able to go into a day and get a lot of activity done in a very short amount of time and get results from it.
[00:29:35] Marc Gonyea: You got to let us sit on the secret, like, what’s going on there? Can we bottle that?
[00:29:40] Rueben Hagen: I think that also just comes from finding who’s good
[00:29:43] at it. And,
[00:29:44] like,
[00:29:45] they are going to be very efficient at it and replicating that. I mean, I didn’t come up with anything I do myself, it’s all came from other people. And so I think a lot of that just comes
[00:29:55] from, like,
[00:29:56] being able to, I mean, having the metrics to see who’s good at it is first very important and see who’s
[00:30:01] good at
[00:30:01] what
[00:30:02] and
[00:30:03] then just going and talk to them. Most people are very happy to share what makes them successful and so go in and figure that out why and then practicing it until it becomes your own, because you’re going to have a slightly different style than the other people.
[00:30:17] Marc Gonyea: And what made you effective? Was it just identifying the right people, your experience, having to build these kind of persona approaches or is it something else?
[00:30:26] Rueben Hagen: I
[00:30:26] think
[00:30:27] it
[00:30:27] was just
[00:30:27] whenever
[00:30:28] I
[00:30:28] had someone that I thought, like, would be a good person to talk to, I’d bounce
[00:30:33] it off
[00:30:33] three or four other people first and figure out how to go about that with other people. I would very rarely, like,
[00:30:41] game
[00:30:42] plan and account
[00:30:42] alone.
[00:30:43] Like,
[00:30:43] even when I was at very small companies,
[00:30:46] I’d work with
[00:30:47] the VP of sales, or at ReversingLabs I’d work with the account executive all the time of being like, “Here’s someone who seems a little bit interested.
[00:30:54] I had a call today with them that was, like, five minutes. Couldn’t quite book a meeting with them, but I think I can get them next time and
[00:31:01] Rueben Hagen: go and
[00:31:01] game
[00:31:01] plan” and that helped
[00:31:02] also give
[00:31:02] me confidence. Going and talk to them. Most people are very happy to share what makes them successful and so go in and figure that out why
[00:31:10] and then
[00:31:11] practicing it until
[00:31:12] it becomes
[00:31:13] your
[00:31:13] own,
[00:31:13] because you’re going to have a slightly different
[00:31:15] style than
[00:31:15] the
[00:31:15] other people.
[00:31:16] ‘Cause it has, like, a new SDR. I think something very important
[00:31:20] and hard
[00:31:20] is having the confidence going to talk to people.
[00:31:23] But if you go and make a game plan with someone who’s done that before and been successful, it helped me get confidence so much ’cause they were just like, “Yeah. Here’s how you do it. I’ve done it this way before and it worked.” And I’m like, “All right, I’m gonna just go do what you did. I’m gonna go do what you told me to do and see if it works.”
[00:31:41] Chris Corcoran: Yeah, and that, then you get competent because you learn stuff, right?
[00:31:45] Rueben Hagen: Yeah, like, well prepared.
[00:31:47] Like, I often, like, I’ll still go on
[00:31:48] Rueben Hagen: to calls.
[00:31:49] Like, I have maybe a few questions if the conversation’s going nowhere to ask them, but I’m not going in with, like, a detailed rigid list, but I like, I feel prepared enough
[00:32:00] to
[00:32:00] kind of
[00:32:01] talk
[00:32:02] wherever
[00:32:02] they want
[00:32:02] to
[00:32:02] take
[00:32:03] the
[00:32:03] conversation and
[00:32:03] go
[00:32:03] with that flow.
[00:32:05] Marc Gonyea: And then it also lets people know who you work with and how hard the job is. Like, when you start talking to people, “Well, here’s what I’m doing. Here’s a call I had.” I think what it does is educate people on the difficulty of the SDR role and the right people really appreciate the effort and energy that
[00:32:19] goes into it
[00:32:19] versus they never hear from you. You’re not getting as many meetings as they would like, or maybe the meetings are, I don’t know, quality, those sorts of things, but people are like, “Oh, this guy Reuben in there” or there’s somebody on your team is shaking and bacon and we got to, we got to help them.
[00:32:31] Rueben Hagen: Yeah, I mean, it’s a very difficult job and unless someone’s been an SDR before, they often
[00:32:37] don’t,
[00:32:38] it’s hard
[00:32:38] to recognize
[00:32:39] that. And so, until you’re kind of walking them through of like, “Here’s what I experienced on
[00:32:43] a day-to-day,
[00:32:43] here’s how the challenge,” they don’t know that, they don’t know how to help you get through that
[00:32:49] and
[00:32:49] they’re
[00:32:49] like,
[00:32:50] not
[00:32:51] going to know why you’re either not doing well or doing really well.
[00:32:56] And
[00:32:56] so
[00:32:56] I think just
[00:32:57] having that constant communication with people you work with helps in so many
[00:33:01] different
[00:33:02] ways.
[00:33:02] Chris Corcoran: So, Reuben, what advice would you give yourself knowing what you know now, back in February of 2000, about being an SDR? I think
[00:33:13] Rueben Hagen: just even more, like, every place you work at has their own style of doing things and what makes them
[00:33:20] good at
[00:33:21] that
[00:33:21] and
[00:33:22] take those in, like, while you’re there, because
[00:33:26] life’s
[00:33:26] gonna move on.
[00:33:27] Failing isn’t bad. You’re going to fail a ton of times
[00:33:30] and as an SDR, you just got to be able to move on from it. And it’s not the end of the world and it definitely felt like the end of the world at times, like, when I had a bad month or something and
[00:33:40] I’d
[00:33:40] be
[00:33:40] very
[00:33:41] hard on
[00:33:41] myself, but just being able to, like, move on through that
[00:33:46] and
[00:33:46] just
[00:33:47] taking things, like, slowly, like,
[00:33:48] not,
[00:33:50] obviously, the job’s very important then you end up generating a lot of revenue for these companies, but you can’t
[00:33:55] win
[00:33:55] every
[00:33:56] single
[00:33:56] one and you’re
[00:33:56] not
[00:33:57] going
[00:33:57] to.
[00:33:58] And
[00:33:58] just
[00:33:59] not being hard on yourself after the ones that don’t work out and finding those, just relax
[00:34:03] with
[00:34:04] the
[00:34:04] job.
[00:34:04] Like,
[00:34:04] it
[00:34:04] can
[00:34:04] be
[00:34:05] stressful
[00:34:05] at
[00:34:05] times,
[00:34:06] for
[00:34:06] sure
[00:34:07] and
[00:34:07] just
[00:34:07] finding
[00:34:07] ways after you just got absolutely yelled at by someone, or you
[00:34:12] had
[00:34:12] a
[00:34:12] deal
[00:34:13] go
[00:34:13] sideways
[00:34:13] that you thought for sure was going
[00:34:15] to
[00:34:15] close, finding ways to lighten the mood is so key and just
[00:34:19] having,
[00:34:20] I think it comes a lot down to the team you have around you and the people you can just talk with after something
[00:34:25] goes bad
[00:34:26] and
[00:34:26] just
[00:34:27] figure out why and then take your mind on it and move on.
[00:34:30] Like, there’s no point
[00:34:32] in wallowing
[00:34:32] not
[00:34:33] just
[00:34:33] move on.
[00:34:35] Chris Corcoran: So, what would you tell someone who had two options? They were going to be an SDR for 12 months, a year, and one would be it’s all inbound. The other, it’s no inbound.
[00:34:48] Rueben Hagen: I
[00:34:49] think,
[00:34:50] for me, what I’ve always thought about the most and prioritize when choosing
[00:34:54] new
[00:34:55] jobs
[00:34:56] or
[00:34:56] many things is what’s going
[00:34:58] to set
[00:34:58] me
[00:34:58] up best down the road. Because
[00:35:00] I’m pretty young, I don’t really care. I mean, I’d like to make as much money as I can this year and do as well as I can, but I’m more care
[00:35:08] what’s going to set
[00:35:09] me up
[00:35:09] 10 years down the road, where I’m going to learn the most where I can, like, get better later in life. So, I think that’s an easy answer of “Do the outbound for 12 months”
[00:35:21] because
[00:35:23] that’s
[00:35:23] where you’re going to find success, I think,
[00:35:25] later
[00:35:26] in sales,
[00:35:27] is being able, it’s way
[00:35:28] harder, like, it’s way, way harder to do outbound for 12 months than inbound the entire time, but you’re going to learn a lot more from itand those skills are way more unique and irreplaceable. Have you seen that, that use the outbound muscle since your time as an SDR?
[00:35:48] Rueben Hagen: Yeah, I’ve used it every
[00:35:49] single day. Like, I mainly do outbound here. I did, mainly did outbound at ReversingLabs is a mix, but, like,
[00:35:58] inbound’s way easier to learn and way less of a challenge. You can more or less
[00:36:03] read office
[00:36:03] office print of it. Outbound, you have to be able to be audible-ready and change it off.
[00:36:09] It’s a way more valuable skill. That’s going to make you more irreplaceable at the jobs you work at. They can find someone quickly to replace someone who does inbound all the time to pick up the phone after they get a trial or a demo
[00:36:24] request,
[00:36:25] but it’s way
[00:36:26] harder
[00:36:27] of a skill to be able to call someone who’s never heard of you
[00:36:30] and
[00:36:30] convince,
[00:36:31] convince
[00:36:31] them
[00:36:31] to
[00:36:31] take a meeting.
[00:36:32] Marc Gonyea: Me, I’d be so upset if I was, I got an SDR job for 12 months, I had nothing but inbound versus somebody who didn’t do nothing but outbound. I mean, yeah, you’re right. your life would be easier, business-work life would be easier, but you, I would, you would almost have wasted a year.
[00:36:47] Rueben Hagen: Yeah, you’re
[00:36:48] going
[00:36:48] to
[00:36:48] get
[00:36:49] bored
[00:36:49] real
[00:36:49] quick. It’s not a challenge.
[00:36:51] Marc Gonyea: Yeah. And you’re not gonna build any skills. I mean, what you’d probably do is put a lot of bad habits unless you’re really, really managed tightly, but even then, on inbound, you’re probably not.
[00:37:00] Rueben Hagen: It
[00:37:00] might
[00:37:01] make
[00:37:01] it
[00:37:01] easier
[00:37:02] for that day. Like, if you told me today I was getting, I was going to get 20 inbound leads of it, so happy. That’s all I got for a year that would get old really quick.
[00:37:14] Marc Gonyea: Yeah.
[00:37:15] Chris Corcoran: And so, you’ve served some time as an, as an SDR leader. Talk about, and now you’re individual contributor as an AE closer, talk about decision to kind of enter the leadership role
[00:37:27] Rueben Hagen:
[00:37:27] Chris Corcoran: and then to move back into an individual contributor. Walk us through your thinking there.
[00:37:32] Rueben Hagen: Yeah, I think a lot of it was what’s going to give me experiences that may be best up later. I know at some point in my life,
[00:37:39] I
[00:37:39] love
[00:37:40] coaching, I love, like, seeing people are new to
[00:37:43] it and
[00:37:44] showing them what made me successful, pointing them out to other people who do other things successful, maybe in a similar
[00:37:51] way
[00:37:51] to
[00:37:51] them,
[00:37:51] but
[00:37:53] I helped lead the SDR team at
[00:37:55] Rueben Hagen: ReversingLabs,
[00:37:56] mainly ’cause I thought it would be great experience to set me up well later and then moved into an account exec role because I
[00:38:04] was like,
[00:38:04] I
[00:38:05] can’t
[00:38:05] really
[00:38:05] see
[00:38:05] a
[00:38:06] path
[00:38:06] to
[00:38:06] being
[00:38:07] a director, VP of sales without being an AE and so I thought, “I’m going to close some doors if I don’t take a closing
[00:38:15] role at some point.” And I think this often, like, you just need to get into that as soon as you’re ready. Like, once you’re able to take the SDR job and make it easy, which is very hard thing to do, then you should go get AE experience because that’s almost always a prerequisite to being, like, a leader in the sales world, is having closing experience. And so I think they go very hand in hand well together, having management experience and being in a closing role, but at the end of the day, I think they’re both pretty critical to have.
[00:38:51] Marc Gonyea: Manager. A Good leader, how to be one.
[00:38:54] Rueben Hagen: I think
[00:38:54] there’s a lot of things and a lot of different ways
[00:38:57] you can go
[00:38:58] about it, but where I’ve seen
[00:39:00] the best
[00:39:02] leaders that I’ve had are people that are able to personalize it for everyone they work with and not just have, like, one-size-fits-all, like, “Here’s my management structure. You’re all going to come in and work in that framework
[00:39:15] and instead be able to adapt it to each person and seeing what they do well.” Like, on my team, we all have different things
[00:39:24] that
[00:39:24] make
[00:39:24] us
[00:39:25] good
[00:39:25] sales reps
[00:39:26] and
[00:39:27] as a leader, being able to find what those are and then have you, like, show someone else on your team how to do
[00:39:34] what you do well, and then them do the opposite,
[00:39:37] Rueben Hagen: I think is really
[00:39:38] key and just being able to identify what people are good at and what motivates them. Because I am motivated very differently than someone next to me. Like, I might
[00:39:49] be,
[00:39:50] I don’t know, less money-oriented or more time-oriented, like, if you tell me I can get two hours back in my day, that’s going to be
[00:40:00] very motivating for me and becoming more efficient at doing something. So, I think it’s
[00:40:05] just being able to identify differences in people and what makes them tick.
[00:40:12] Chris Corcoran: And now, as a closer, what makes you a good closer?
[00:40:15] Rueben Hagen: I
[00:40:15] think what makes a good closer is being able to
[00:40:20] relate to each person you work with really
[00:40:22] well and not trying to fit them into your selling structure and instead adapting to their buying structure and
[00:40:30] just
[00:40:32] relating with them as a person. Like, yeah, they’re an employee and their role might be an engineering manager, but, like, what’s actually important to them and figuring that out and then just being able to have,
[00:40:46] uh, very conversational talk with them rather than just purely, like, “What are you going to do for me?”
[00:40:54] Rueben Hagen: And I think it just
[00:40:55] taking
[00:40:56] those
[00:40:56] meetings
[00:40:56] that are very structured kind of going into people, have
[00:41:01] some, like,
[00:41:02] nervousness going into a sales call of, “Oh, am I just going to get, like, a PowerPoint presentation the entire time and turning it into, like, what’s going to be beneficial
[00:41:12] for
[00:41:13] them?”
[00:41:14] and just, like, at the end of the call, whether it’s a fit or not, going away on friendly terms and being like, “All right,” like, “That’s someone I talk with again, even if, like, it
[00:41:22] might not be a fit for us, I had a good time talking with them for half an hour.”
[00:41:26] Marc Gonyea: In addition to that, what’s a skill? So, you’re new in the chair as a closer and every SDR in memoryBlue who’s dying to learn about that. I don’t throw a dime to do it, a lot of them are, but they want to learn about it. What are some other skills you’re like, “Okay, I’ve been doing this for a month or so? These are the skills that I know
[00:41:42] I think I got, I have to work on develop.”
[00:41:45] Rueben Hagen: Yeah,
[00:41:45] I
[00:41:45] think
[00:41:47] it’s about,
[00:41:48] like,
[00:41:49] continuing that relationship because in S, as an SDR, you set up the first meeting, you
[00:41:53] might not talk to them again. And so, it doesn’t matter as much whether you leave on good terms or not as long as that meeting happens, but
[00:42:03] when you’re in a closing role, you’re going to have a 5, 6, 7, 15 meetings with them, you need to be able
[00:42:09] to continue that relationship and have it go for a while and then really be an expert in their business. Like, as an
[00:42:16] SDR, you need to be able to move quickly through calls and accounts and get a high volume, but once you have an
[00:42:24] initial meeting with them, you need to be an expert in what’s important to them, what their business is about, how they’re making money. Like, you need to have
[00:42:34] much more research skills into their company. And so, I think that’s something I’m still learning, is all those skills because they come into play much more. You need to be
[00:42:44] well more prepared for a 30-minute discovery meeting and then demo than you do for a 2 to 5 minute, like, cold call with them.
[00:42:54] Marc Gonyea: Interesting. That does definitely good, good take, good perspective. So, you’re a Datadog, which it’s not cyber, right?
[00:43:02] Rueben Hagen: Nope.
[00:43:02] It’s,
[00:43:02] like,
[00:43:03] monitoring
[00:43:03] and
[00:43:03] observability.
[00:43:04] Marc Gonyea: So, as you know, you’re definitely a well thought-out individual, how have you evaluated these companies? So, you told us a little bit about cyber, how did you evaluate, uh, Datadog as a place? Different tech? You know, I don’t want to put words in your mouth because you may say the things I said, or you may say different things,
[00:43:23] why did you decide that this is where I’m going to put an anchor and learn how to close here? What made you choose them?
[00:43:29] Rueben Hagen: Yeah.
[00:43:30] I think
[00:43:31] some of those very important to me is just who I’m going
[00:43:34] to be working
[00:43:35] on
[00:43:35] a
[00:43:35] day-to-day
[00:43:35] level with and if I want to work with them on a day-to-day level. And so, I was reached out to by a manager here, talk to them a bunch of times
[00:43:45] and decided, like, that him and the team that was going to be working with is someone I liked to be around, just very smart people I met here,
[00:43:56] where there’s a lot of opportunity to grow in many different ways. I think coming to Datadog opened a lot of doors for me, rather than closing them, maybe at a smaller company with something, there’s
[00:44:08] so many paths to take forward here and I think coming to Datadog, just, like, it just allowed that branch to open a lot. And just after doing research, Datadog seemed like a good place to be with a lot of right people and so I pulled the trigger.
[00:44:26] Marc Gonyea: That’s great. What’s your target? What’s your territory?
[00:44:29] Rueben Hagen: So, we get XXXXXX
[00:44:31] accounts. It’s not really broken up by a certain territory
[00:44:35] or
[00:44:35] anything. It’s commercial, so it’s under a thousand employees. I talk to a lot of startups, which I really like. It’s really cool ’cause they’re very passionate about what
[00:44:45] they
[00:44:45] do.
[00:44:46] Like,
[00:44:46] they do that 24/7 and so just doing that research in their business is really important to me. Like, “Hey, this is really cool what you’re doing.” And I get to talk to a lot of really cool startups who have great ideas and seeing what they’re doing.
[00:45:01] Marc Gonyea: That’s exciting. And you’re putting these SDR skills to good use, it sounds like, obviously.
[00:45:05] Rueben Hagen: Oh yeah. I’m still making lots of
[00:45:06] calls
[00:45:08] and
[00:45:09] that’s
[00:45:10] the fun of it, is being able to do that research into them and then go talk with them and, like, they’re very passionate about it and so they’re excited about tools that I can help them out as well and so they’re very excited about the opportunity and yeah, it’s pretty cool.
[00:45:25] But you’re booking meetings for yourself?
[00:45:27] Rueben Hagen: Yep.
[00:45:28] Marc Gonyea: Like, that’s great. You use no one to get mad at.
[00:45:30] Rueben Hagen: Yeah.
[00:45:31] Yeah.
[00:45:32] Look in meetings from itself. Yeah, it’s um, and then having that
[00:45:36] initial
[00:45:36] call
[00:45:36] with
[00:45:36] them
[00:45:36] is, yeah.
[00:45:37] Chris Corcoran: So, having been an SDR, now you have the good fortune of having SDR support. Is that, that you share that SDR resource with some teammates or is it a round-robin? What exactly is the setup?
[00:45:51] Rueben Hagen: Yeah. So, we have kind of, both of we’ll get the SDR we work with.
[00:45:56] The SDR supports four different AEs. We each give a certain number of target accounts to go after and then there’s ones
[00:46:07] that will also be passed around or on a round-robin basis. If something comes
[00:46:10] in to him and she follows up maybe on the inbound lead he got and it’s not assigned to anyone
[00:46:15] that I get passed around, but we
[00:46:17] give them certain target accounts to go after, which are often, like, bigger ones and they’ll maybe go after the engineers while we go after the engineering directors and the VP.
[00:46:27] Chris Corcoran: I see. And so, what are you doing or aspiring to do as an AE to really have a strong relationship for that SDR who supporting you?
[00:46:38] Rueben Hagen: Yeah,
[00:46:38] I think
[00:46:40] myself and the other
[00:46:41] three AEs
[00:46:43] that the SDR supports all have very different styles and so just bring them in on as many things we do and why we, explaining
[00:46:51] why I think it’s so important behind it.
[00:46:54] Being, like,
[00:46:56] on discovery calls that they sit in why we asked a certain question, what actually opened up the conversation, because maybe you have someone who, like, is pretty shut down and then all of
[00:47:07] a sudden, they open up out of nowhere
[00:47:08] and just figuring out why and what works, um, I think was very important.
[00:47:14] Chris Corcoran: Very good. And so, what do you see for your future, Reuben?
[00:47:18] Rueben Hagen: I’m not really sure. I think just figuring out how to be successful as an AE is first on the plate. I have a lot of great examples of people around me and I’m not too worried about being successful as an AE, but that’s the first step. I think you need to master what you’re doing at
[00:47:36] before
[00:47:37] being able to move on to something else because it’s still
[00:47:40] going to be needed in the next role. Like, if I was going to manage a team of AEs, I’d want to be comfortable saying like, “Yeah, I was a very good AE
[00:47:48] myself. This is what made me good. Here’s something you might be able to copy if you want.” And so, I think that’s just getting experienced in the role is first on my plate and see what happens from there.
[00:48:02] Chris Corcoran: As we kind of wind down, you had, you’ve had an opportunity to get a lot of exposure as an SDR, what would you say is the biggest mistake SDRs make?
[00:48:13] Rueben Hagen: I think trying to overanalyze every single account in person before you talk to them. Like, you
[00:48:23] Rueben Hagen: might be able to guess
[00:48:24] what their needs are, but, like, until you actually walk with them and ask them, “Hey, like, what’s annoying you?” Like, “What’s frustrating about your job?” You don’t really know that because it’s going
[00:48:34] to be different person to person. So, I think just picking up the phone and talk to them. I think I’ve, as someone
[00:48:41] who likes to plan things out and research, I spent way too much time trying to learn everything about them before going to talk to them and then as soon as I talked to them that all get thrown out the window. And so, just picking up
[00:48:55] Rueben Hagen: the phone and talking to people.
[00:48:57] Rueben Hagen: And I think
[00:48:58] approaching calls as being like, “This is a way to research them” rather than, like, approaching every single call is, like, “I have to book a meeting with this person,” like, and get
[00:49:08] super hyper-focused on that. It’s just like, this is a research call to learn if they’re a fit or not and I’m just researching about them, then putting them in the bucket of like, “All right. They are a really good fit for us. It’s a good time for them.”
[00:49:22] Or they might be a good fit, but it’s not the right time or just, they’re not someone or a company we need to talk to anymore. And just a mentality.
[00:49:33] Marc Gonyea: Reuben. That’s good, that’s a good take right there. Hot. That’s a good take, because that’s, folks who don’t organize and plan their approach, usually because of call avoidance, don’t roll that way and they get a little desperate and then try and book everybody versus being strategic with it
[00:49:49] and you can still do your job and be a good SDR, that you’re much more effective and there’s a lot of less cognitive dissonance going on in your mind. You’re not putting this pressure on yourself to plug everybody.
[00:49:59] Rueben Hagen: Yeah. Definitely. Like, it’ll come to you if,
[00:50:01] like, if you’re just calling, trying to learn more about them,
[00:50:04] Rueben Hagen: it’s going to come. Like, you don’t need to try to force everyone you talk to to be that right person. Like, pick up the phone, talk to them and that will, it will come.
[00:50:15] Chris Corcoran: Reuben, your AE is showing. But what I mean by that is, is when you, when you’re prospecting for yourself as an AE, it’s not all about just setting up the meeting, it’s qualifying this person in or out and it’s, that was my second favorite answer, right? Because you don’t waste time on something that is not going to go anywhere, but when you’re just an SDR and all of your mentality is on, is a book and occur and that’s all you care about, then you’re going to try to talk your way into some opportunities or some meetings that aren’t going to go anywhere, just because that’s the outcome that you’re fixated on,
[00:50:50] but it sounds to me like, it sounds, I, if I was to bet, you’ve always had that mentality of “Listen. I want to make sure that I have high quality and want to do it the right way and if I do it the right way, that’s the fastest way to get to where I want to go, is by doing it the right way”
[00:51:04] and the shortcut is actually doing it the right way.
[00:51:07] Rueben Hagen: Yeah. And I think something that I learned over time is how easy it is for people to tell your intentions over the phone. Like, you don’t if it gets that easy.
[00:51:15] but someone can tell really quickly based off your tone, if you’re just going to force them into a meeting no matter what and don’t care what they
[00:51:23] say, or if you’re listening and actually, like, just trying to talk with them, figure out if it would be a good fit. That comes
[00:51:31] of way more than I realize when I started. Like, your intention comes off so easily on the phone, even if they can’t see you and don’t know you, like, people pick up on that really quickly, on just your tone of voice and, like, what questions you’re asking them.
[00:51:49] How did you come to that realization?
[00:51:51] Rueben Hagen: By failing a lot. And I think just doing it over, over, I definitely quite often would push to just get that meeting no matter what and I ended up probably losing out more meetings than I would’ve gotten if I hadn’t
[00:52:03] pushed
[00:52:04] as hard. Because, like, maybe they’re having a bad day and no matter what, you’re not getting a meeting that day,
[00:52:12] but if you accept it that day and call them back a week later, all of a sudden you’re going to get them. And so, I think it was just practice and experience
[00:52:21] Rueben Hagen: and seeing it happen over and over.
[00:52:23] Marc Gonyea: It’s like being okay with the ‘no’, but in a different way. You’re not looking for ‘yes.’ That’s a hundred percent. So, yeah. Reuben, that’s some good stuff there, man.
[00:52:34] Rueben Hagen: Thanks.
[00:52:35] Marc Gonyea: Well, we appreciate you joining us.
[00:52:37] Chris Corcoran: Yeah, Reuben, I look forward to seeing you tomorrow and I, you know, the, thank your mom for her understanding on her birthday.
[00:52:43] Rueben Hagen: We’ll see. I’ll get
[00:52:44] her on the phone with you.
[00:52:46] Chris Corcoran: Yeah. Well, we, we don’t see you this time. We’d certainly want to see you next time we’re in town.
[00:52:50] Rueben Hagen: Absolutely.
[00:52:51] Chris Corcoran: So, we appreciate all the wisdom today and, uh, we’ll be watching you and rooting for ya over at Datadog and hopefully you can, now you’ve got two other memoryBlue alumni working over there that if you can keep up with those two, you’re going to be having some real success.
[00:53:06] Rueben Hagen: Yeah, I got a strong group of peers around here from everyone and so, just, yeah.
[00:53:11]
[00:53:11] Rueben Hagen: I mean, that’s what I like, being able to have those people around you to compare yourself to and figuring out what they’re doing.
[00:53:17] I mean,
[00:53:17] it’s kind of a competition, but not really at the end of the day. Like, we want everyone to succeed and I want like us all to do well,
[00:53:26] so yeah. It’s great having the
[00:53:28] memoryBlue to Datadog pipeline flowing.
[00:53:31] Chris Corcoran: Yeah. let’s keep it rolling. All right, Reuben. Thank you, Reuben.
[00:53:33] Rueben Hagen: Yeah. Thank
[00:53:35] you. It was
[00:53:36] a blast.