Episode 81: Jesse Matthews – Picking Your Best Opportunities
Choose the battles you know you can win. Focus your time and energy to grow your career, your pipeline, and your team in the most impactful ways.
Now an Account Executive at Thycotic, Jesse Matthews debunks the belief that a successful career must be linear. After a year in the DM role at memoryBlue, Jesse decided to pursue the AE role he’d always wanted. The diverse exposure to various clients and technologies as a DM allowed him to build a network that would help him grow in the right direction.
In this episode of Tech Sales is for Hustlers, Jesse discusses ways to weed out dead-end prospects, prioritize opportunities for growth, and build professional relationships as your career evolves.
Guest-At-A-Glance
Name: Jesse Matthews
What he does: He’s an Account Executive at Thycotic.
Company: Thycotic
Where to find Jesse: LinkedIn
Key Insights
⚡ Always pick your opportunities. As a salesperson, you need to learn to identify, nurture, and finally pursue the most qualified leads. Accept that you can’t close every deal and learn to embrace the objections. Jesse says that one of the biggest lessons he learned in sales is to pick his opportunities. “The biggest thing that he taught me was probably picking your opportunities because, as a salesperson, you want to think that you can close every deal, but that’s just not realistic. So it’s picking the ones that you know are good from the get-go and working on those, and devoting time to them. Because if you’re taking meetings that are BS (for lack of a better term), you’re just going to be wasting your time, and then you’re not going to close as much.”
⚡ Build relationships. Relationship building is essential in every career, but it’s crucial in sales. Not only does it help you connect with your prospects and close more deals, but it also allows you to explore more career options. Jesse is a people’s person, and he thinks it’s one of his strongest assets. “I think I’ve just tried to be advantageous about where I’m going, where I already know people. That’s a lot of that. With Thycotic and ThreatConnect, I already had relationships there, so I knew I could come in and grow. And in a lot of the big companies, I don’t, to be honest with you. Plus, I think that it is a little bit scary, I’ll admit, to go to a big company where you are, sometimes, just a number, as opposed to [a place where] even the CEO can know your name, sometimes even at Thycotic, which has 500 plus employees.”
⚡ Roll with the punches. You can’t win every deal in sales, but you can learn from every experience. If you want to thrive as a salesperson and advance in your career, you’ve got to make the most out of every experience and always find a learning opportunity. Jesse says, “Get the most out of each experience you have. So being a DM, taking the step back, moving to the ISR role, just roll with the punches, have your goals in place, but don’t get so focused on one thing that you don’t see the other opportunities around you.”
Episode Highlights
Everybody Has Their Own Path
“Everybody has their own path. I had a couple of guys, one that we talked about a little bit earlier, Matt Bernfeld. […] He was awesome. He hit the phones immediately. He was just a killer. But he did the whole Capitol Hill thing, didn’t love it, and ended up saying, ‘I want to get into something else.’ He came through the interview process, and I remember, I forget who interviewed him with me, but they really grilled him — way more than anybody else — to make sure he was a good fit. And he ended up getting hired and crushing it. But I think during the DM process, it was really figuring out how to manage a lot of different personalities that aren’t the same as you. I guess it’s the easiest way to put it.”
Some Career Moves Are Not a Step-Down. They Are a Fresh Start
“For me, it wasn’t that hard a decision because I got to the management level. I learned a lot, took that step up, but it wasn’t like I was typically taking a step down in that path. I was just going back to another path and kind of starting over. So I never really looked at it as a negative. Actually, one thing Christine pitched was being a team lead or a team lead/player, to which I told her, ‘I just want to go back to being an individual contributor.’”
Go Where There’s a Path
“I finally made the decision, ‘Hey, I don’t want to be a DM. What can I do here?’ When I was going back into the interview process — I don’t think I actually really interviewed — you guys made it very clear, go where there is a path. And a couple of people that had already paved the way were Cat Doulic and Ben Yonic. […] They had gone through the path. They were BDRs there. Christine took them in, and at that point, they were already up to what we call the ISR role. So I knew what I was getting into. I knew it could be fast, and it was four months before I was sitting in a different seat within ThreatConnect, which is cool.”
Transcript:
[00:00:28] Marc Gonyea: Chris, I’m so excited. Captain America, Jesse Matthews is back in the house.
[00:00:56] Chris Corcoran: Captain America.
[00:00:58] Jesse Matthews: Captain America.
[00:01:00] Chris Corcoran: That’s a girl’s best nickname.
[00:01:01] Jesse Matthews: It is. I still remember when Chris gave it to me. Yeah. You brought up a picture of when I was playing Ultimate Frisbee and it was a picture of me about the throw,
[00:01:12] and you were like, “Captain America,” I think he was announcing when I was leaving, getting promoted.
[00:01:19] Marc Gonyea: Promoted. Yeah, it’s been
[00:01:21] awhile.
[00:01:21] Jesse Matthews: It has. Good to be here in the office.
[00:01:25] Marc Gonyea: Welcome back. All right, Jesse, we were just catching up on some of that with the listeners, but let’s, let’s let them get to know you a little bit.
[00:01:32] So tell us a little bit, before it happened to this, where you’re from, where you grew up, what you were like as a kid and we’ll kind of go from there.
[00:01:39] Jesse Matthews: Yeah, sure. So, I am kind of a hometown kid. Lived out in Fauquier which is only an hour away, Go Fauquier your county, grew up playing sports, hanging out on the farm,
[00:01:50] no, not really, but yeah, I went to Fauquier high school, played football, basketball, lacrosse, was always playing sports year round. Loved it, lacrosse. I think I was probably the best at football, arguably, not so much basketball, just being a larger individual, but, yeah, lax was my favorite. I could have gotten to college and played,
[00:02:11] I probably would have at, like, a D1 program. Wasn’t that good.
[00:02:14] Marc Gonyea: Right. Would have been nice. So, let’s go back. What were you like as a kid? Sorry, siblings?
[00:02:18] Jesse Matthews: Siblings. I am one of four. I was the third one, so I was the first boy, but then my little brother came along, which was both a blessing and a curse
[00:02:29] ’cause then he became the baby.
[00:02:31] Marc Gonyea: So, two girls and two
[00:02:32] boys and you’re a third of the four of them.
[00:02:35] Jesse Matthews: So, I got terrorized by two older sisters and then I got terrorized by a little brother.
[00:02:41] Marc Gonyea: What was that like with that many kids? Just curious.
[00:02:44] Jesse Matthews: I loved it. My wife now, she’s an only child and she talks about how she always wanted to have siblings,
[00:02:50] so for me it was like, you always have a couple of best friends, growing up, you know, I had trouble making friends at school, but it’s kind of nice going home and doing whatever when you’re little.
[00:03:00] Marc Gonyea: That’s great. Just give your wife a shout-out real quick ’cause she’s always been, you know, whenever we had memoryBlue events, she was almost always there, so supportive, supportive
[00:03:08] spouse.
[00:03:09] Jesse Matthews: Yeah. Yeah. Shout out, Alexis Massey, soon to be, at some point, Alexis Matthews whenever she gets around to it, but priorities.
[00:03:17] Marc Gonyea: When did you get married?
[00:03:18] Jesse Matthews: We got married 10/10/2020.
[00:03:22] Marc Gonyea: All right. So, we’ll go back. All right. So, you’re in high school, you’re playing sports, what’d you think you wanted to be when you grew up?
[00:03:28] Jesse Matthews: That’s
[00:03:28] a great question. I think, probably graphic designer. So, I knew I wanted to go into something kind of marketing-related. So, ideally I was thinking, like, get a job at an ad agency, maybe go into something graphic design, so I’m creating stuff for companies for ads, because I took a graphic design class, like, my freshman year of high school.
[00:03:48] So, that was kind of the goal, maybe, junior year and then senior year I really wasn’t sure. I just knew I wanted to go into something marketing.
[00:03:56] Marc Gonyea: And then you end up going to Virginia Tech?
[00:03:58] And what was that like?
[00:03:59] Jesse Matthews: That was amazing. So, my sister went there the four years before I did, older sister. So, she was there, fell in love with the, obviously being a football player, fell in love with the football program, which has hit a bit of a rough patch,
[00:04:16] that’s okay, as of late, I know, Chris, you understand, Mike little bit, but, that was awesome. That was always my top choice, when I got it, and there was no question I was going there.
[00:04:25] Marc Gonyea: Did sales kind of rear its head at some point, like, in high school or when you were in college or?
[00:04:33] Jesse Matthews: Yep. So, we were just talking about him,
[00:04:35] Brian Collins actually came in to one of my marketing classes to sub, so it wasn’t even like I started into the sales immediately, so he sobbed and right at the end he gave his, like, 32nd elevator pitch about, “Hey, this is the sales program. It looks great on a resume. If you’re looking for something to add or just, you know, some extra classes to take, just do it.”
[00:04:56] And I was like, I don’t have anything extra that I’m taking. I was just a marketing major, so I said, “Why not?” And also I worked at a winery where I was basically just behind the counter and was selling wine, kind of given the spiel of, “Hey, this is a fruity blend,” whatever the case may be. So, I thought, “Sales, that doesn’t sound so bad.”
[00:05:16] You know, I’ve kind of done that in the summers. Barrel Oak.
[00:05:20] Marc Gonyea: Barrel Oak.
[00:05:21] You know, when you have a good person, a good employee, a person, you’ve worked there three summers in a row, right, so if you’re not good, then I ask you to come back.
[00:05:29] Jesse Matthews: It was fun.
[00:05:30] Marc Gonyea: It was. What year was that
[00:05:32] marketing class with?
[00:05:33] Jesse Matthews: It was junior year, the fall semester and then added it in between and had to take, I think, like, six courses to get the concentration, add it to the resume or add it to the diploma. It was good to go, but I loved that.
[00:05:49] Marc Gonyea: What happened with marketing major? And you had to take what, how many glasses?
[00:05:56] And then what’d you like about it?
[00:05:58] Jesse Matthews: So, one thing compared to some classes, as we all know, sometimes the professor just pulls up PowerPoints and kind of walks you through things, and Collins was all about getting you ready for the real world and real-world sales experience. He had a book that I think he might’ve said was optional to buy, but, like, every lesson that he tie, he would tell us these real-world examples,
[00:06:21] and I still remember, he talks about this guy who closed or sold his company for, like, $800 million, and he got whatever the valuation was from I think Goldman Sachs, and he, like, sat outside for a little bit, he walked upstairs, he walked in the room and he took off his sunglasses and he just shoved them across the table with, like, the entire Goldman Sachs board there and then just walked out of the room and just sat outside until somebody ran up to him and was like, “We’ll give you a hundred million more.”
[00:06:48] So, that story definitely stuck, that was, like, that sounds awesome.
[00:06:53] Marc Gonyea: That’s what I want to do. I still wanna do that when I grow up. Okay. So, what happened when you graduated?
[00:07:01] Jesse Matthews: I graduated. I was in line to start here. Yeah. How did all that go down? So, actually LinkedIn. Kristen Wisdorf. I believe it was Kristen reached out on LinkedIn and said, “Hey, why don’t you stop by the booth?”
[00:07:13] This was the spring semester, fall semester. I think I stopped by and just said hi, because either one of you or Kristen had come in just to speak, so you were already on my radar. I talked to Kristen again. I remember she immediately came up and said, “Hi, Jesse,” and I was like, “I don’t know how you remember my name, but what’s going on?”
[00:07:31] And, we chatted for a while, and I talked with a couple people that were SDRs at the time and I was pretty sold at that point. I got the interview the next day, came in and the rest is history.
[00:07:41] Marc Gonyea: So, you think you got an email first? I’m most curious ’cause we always like the recruiters that reach out to people proactively and say, “Come by our booth.”
[00:07:49] So, do you remember getting the email first or was it the class? I mean, I’m asking a lot of you, but I don’t know.
[00:07:53] Jesse Matthews: I think it might’ve been the class first, actually. It was already on my radar and I got the LinkedIn, “Hey, why don’t you come swing by the booth?” And then went from there, yeah.
[00:08:02] Marc Gonyea: This summer
[00:08:02] that’ll be seven years ago, right? I think four or five or six years ago, because you got out of Tech in 2016. Yep. Okay. All right.
[00:08:09] Jesse Matthews: I’m an old man now.
[00:08:11] Marc Gonyea: So, then you started, so, you graduated in May in 2016, you started in August, 2016. What was that like? Did you kind of know what you’re getting yourself into or did you not know?
[00:08:21] Or, if people have varying degrees of a familiarity with what it’s going to be like?
[00:08:26] Jesse Matthews: I would say the expectations were set what metrics I was going to be doing and kind of what the process was for making calls, getting meetings, all of that, but the actual doing of it was not expected, just a little bit different than what I thought walking in on day one, not a bad way just, I would say different.
[00:08:50] Marc Gonyea: Enlighten us,
[00:08:50] what does that mean?
[00:08:51] Jesse Matthews: Yeah. So, like, I guess, from an SDR perspective, you think, okay, you’re making a hundred calls a day, you’re booking meetings with folks, like, that doesn’t sound, it doesn’t sound that difficult, and then you get into it and you’re like, this is a craft that you have to hone, and it’s not as simple as picking up the phone and being a nice person.
[00:09:08] Yeah, exactly.
[00:09:10] Barrel Oak winery. So yeah, that was basically walking on the first day and going, “Wow, this is, you have to know a lot more than I thought you were going to at first.” I can’t just charm the pants off people.
[00:09:23] Marc Gonyea: It’s Captain America.
[00:09:26] Chris Corcoran: Captain Linger, man.
[00:09:28] Marc Gonyea: Who was around you? Like, who was your, what was your kind of cohort
[00:09:32] group?
[00:09:33] Jesse Matthews: So, around me was Sean Joyce, was originally my mentor. Sean Joyce, and then Jeremy Wood was there, Frank Taylor was, he wasn’t my manager, but he was, I guess, just down the row monitoring.
[00:09:52] Chris Corcoran: That’s a pretty good row.
[00:09:54] Jesse Matthews: Yeah, it was. Yeah. And then Emma, I can’t remember her last name. She was an intern. I forgot what she went on to do.
[00:10:01] Marc Gonyea: Okay.
[00:10:02] Chris Corcoran: Oh yeah, yeah, yeah.
[00:10:05] Yup. Yeah. Way back in the day. Yup.
[00:10:08] She was just interning. She got into iFoundy’s in New York City.
[00:10:11] Jesse Matthews: There you go.
[00:10:12] Marc Gonyea: That’s what I mean.
[00:10:18] Anyways. All right. Do you remember your client?
[00:10:21] Jesse Matthews: The first one that I was put on was Tiger Analytics.
[00:10:24] Chris Corcoran: Oh, wow. Still a client.
[00:10:26] Jesse Matthews: Still a client. PPM, went to manage it at one point. No, again, the head there, but Tiger was first, and then.
[00:10:33] Marc Gonyea: I can’t, can’t believe you were on Tiger. Sorry, I just wanted to take a deep breath. That was a long time ago.
[00:10:39] We’re still cranking it out.
[00:10:42] You’re paving the way, man. All
[00:10:45] right, so you are a tiger, and what would you say? Something else before I cut you off?
[00:10:49] Jesse Matthews: I was going to say, the second I think was Neustar. Neustar. Okay.
[00:10:53] Marc Gonyea: I’m trying to get them to call us back. Linda, call us back. Like, okay. They’ve been the client a couple of times too.
[00:10:59] They’re a great company.
[00:11:00] Jesse Matthews: Yeah, they are. They’re growing massively too.
[00:11:03] Marc Gonyea: What was it like to learn the phone, the phone game?
[00:11:06] Jesse Matthews: Tough, but I still do remember Sean Joyce, actually, he did my first mock cold call and he calls me up or I call him, I’m like, “Hey, it’s Jesse Matthews. How’s it going? Yada, yada,” and then he just hangs up on me and I didn’t realize it at first, like, brand new
[00:11:27] I didn’t hear the noise, he goes walking around and he’s like, “Yeah, I hung up on you.” And I was like, “Oh, okay, look, what I do wrong?” He goes, “No, I’m just showing you. That’s the worst thing that’s going to happen,” which I thought was a great lesson, personally. So, but yeah, learning, it was tough. I think, learning the elevator pitch, learning enough to be dangerous as you guys love to say was tough, but at the same time, after a good, like, three months or so you just get comfortable for the most part.
[00:11:50] Marc Gonyea: What did you
[00:11:51] well, what became speaking of superpowers to Captain America, the whole podcast, what wasyour superpower? Like, what, what did you kind of kind of make your album part of it?
[00:12:01] Jesse Matthews: I did a presentation. I, at one point, it was the followup calls. Being able to get something on the phone, it might be a bad time getting enough in place that they do want you to call back at some point,
[00:12:12] and then when you get them on the phone, the next time, it’s just a super short, “Hey, this is what we talked about. You said this might be important. Why don’t we just schedule a call?” And it just made the whole conversation a lot simpler. And there were stats. I think at some point, somebody said, like, they booked, like, 40% of their meetings and I was somewhere around there just off of that.
[00:12:32] Marc Gonyea: All right. That’s, you gotta know your shot, know your offense. Who else was good? So, we mentioned people, but who else besides yourself? Who else was really good at the time you were there?
[00:12:45] Jesse Matthews: The time I was there, I think the best person just out of the box for what lack of a better term was
[00:12:51] Chelsea Kothman. She came in and booked, like, her first call ever. And I was like, “Okay, great.” She was pretty, pretty incredible there.
[00:13:01] Marc Gonyea: She moved on.
[00:13:02] That’s right. Okay. Anyone else?
[00:13:04] Jesse Matthews: What I would call the “process” was definitely Joey Plesce. He was very nice. Yeah, very, everything was detailed. He followed the same script basically every time and it worked.
[00:13:15] I can even see that right next to me.
[00:13:18] Chris Corcoran: Who’s your initial manager?
[00:13:20] Jesse Matthews: Originally, it was Catherine Fan. So, that was only a week though. She left, she let me know that Thursday, I started on that Monday. I didn’t really know what to think and Sean Joyce, I think, I don’t know if he got hired out or he went on somewhere else, but he left on that Thursday,
[00:13:39] so then my mentor and my manager left and I was like, week one, week one. I was like, “I don’t know what I got into,” but Frank Taylor. Yeah.
[00:13:49] Chris Corcoran: You lose
[00:13:49] your mentor and your manager in the first week?
[00:13:52] Marc Gonyea: But did we tell you before, did your manager say that before you started, is how you said? Okay. No. Okay.
[00:13:58] Jesse Matthews: So, it was interesting.
[00:14:01] I didn’t really know what to think. I mean, I’m kind of a person where things happen. You just go with the flow. So, there wasn’t a point where I was thinking about jumping ship or anything, but you know what, this happens, it’s bad timing when I started, but I’m sure things will be figured out.
[00:14:16] And so, I just kind of waited.
[00:14:19] Chris Corcoran: So, and then what happened? So, who took over for Catherine’s?
[00:14:22] Jesse Matthews: Frank Taylor. He assured me, he sat down the road from me and he’s like, “Don’t worry. Like, we’ll figure it out.” I think he came by at one point, and you were like, “I haven’t forgot about you. We’re going to get, get you on a team,” and Frank was like, “You’re going to be on my team.”
[00:14:39] Marc Gonyea: Yeah, you know what? I mean, it’s a scary job, and there’s some ups and downs to it, and it’s really fast-moving with clients and the people, so it can be a little overwhelming at first, because of all the shit we’re trying to teach you how to open the call, how to build a list, how to run your weekly calls, how to sell the meeting, how to talk about the meeting on the weekly call, how to follow up with AE, there’s all these little things you have to learn.
[00:15:04] And then, then you got to call people like parents age and get them on the phone and get them to talk to you. It’s, there’s a lot going on. Right now it kind of seems like old hat, right? Like, when you’re first doing this, and it’s your first professional career, you and your internship, I think when you were doing that hospitality thing, you had a tough gig before, but, like, it’s a lot.
[00:15:23] So, you’re in the role and doing your things, you, Frank gets you promoted, things are that you’re working with the process. Is that what you call it? Plus the process”
[00:15:31] Jesse Matthews: That’s how I would define him.
[00:15:35] Marc Gonyea: He just did a presentation, is probably the best one, including the four or five that we saw. He’s good at his job. He is. So, what’d you think you wanted to do, like, ‘ cause you need your first job to kind of, your eyes are just getting open to the thing, what’d you think you wanted to kind of take things?
[00:15:50] Jesse Matthews: Originally,
[00:15:51] it was getting hired out and getting to that AE role. I wanted to be the guy that took the meeting, that hopped on, asked the questions, set up the next steps and then eventually closed the deal at the end.
[00:16:02] Chris Corcoran: You wanted to be the guy who threw his sunglasses?
[00:16:05] Jesse Matthews: Yes, exactly. That was the goal originally.
[00:16:09] Marc Gonyea: And then, how did that go?
[00:16:10] Because you must’ve been good at your job. I don’t have the numbers in front of me, but, you know, seven, eight months in, he said, “Hey Jesse, you want to be the manager?”
[00:16:18] Jesse Matthews: Yeah, I worked for another company or it was contracted out by Clare Bridge, yeah, which was an OG, I remember doing the role-play with the Clare Bridge pitch that you guys send out.
[00:16:28] Marc Gonyea: We still use that.
[00:16:29] Chris Corcoran: Tiger Analytics, New Star and Clare
[00:16:32] Bridge.
[00:16:34] Jesse Matthews: Yeah It was great. Clare Bridge went really well, got them a couple of really great meetings, and then it got to the point where Frank was leaving, and he mentioned that before he left, he said, “You need to ask about becoming a delivery manager,” said, “You’re great with clients.
[00:16:51] You know what you’re doing,” so on and so forth, and Frank was kind of the first one, like, watching him kind of made me think, “Maybe I want to do this,” so then Clare Bridge ended up making an offer, you guys, I started talking to you and then it was a tough decision from there, but yeah.
[00:17:08] Marc Gonyea: Was it Jason Snyder, at Clare Bridge?
[00:17:11] Jesse Matthews: Sounds familiar.
[00:17:11] Marc Gonyea: Not
[00:17:11] somebody else. Okay. Interesting. Okay. Yeah. So, you did a good job that a client wants to make a move on you earlier. So, you just had to stay with us, which was great, and let’s talk about that. So, you went to the delivery manager role, but so, that’s a lot, that’s, like, another version of the SDR role, but worse because you don’t really, you got to worry about other people and their shenanigans.
[00:17:30] That’s the T leagues, right? That’s the big league out there. It’s also, yeah, it’s kind of headaches, job two and a bit challenging, yeah.
[00:17:38] Jesse Matthews: Definitely is.
[00:17:40] Chris Corcoran: Got it. So, you were, you were an SDR, that job, we talked all about how challenging that is, but you were able to kind of figure it out really quickly, prove that you were really strong,
[00:17:48] so much of the clients wanted to hire you, ultimately you saw leadership from Frank and you decided, “Hey, you know what? I want to explore being an SDR leader.” So, talk about what that was like and how it was different than what you thought it was going to be.
[00:18:02] Jesse Matthews: Yeah, I wanted to do it because growing up playing sports, I always loved kind of mentoring,
[00:18:08] I’ve got the little brother who has played sports and I always thought, you know, “Okay, this is something that I want to devote time to, bettering other SDRs and kind of maturing and growing that process,” right? So, starting, it definitely is different because not every SDR at memoryBlue was straight out of college,
[00:18:25] so at one point, my team so lovely pointed out to me that I was the youngest person on my own team.
[00:18:34] It was great. They were, they’re a handful.
[00:18:37] Marc Gonyea: So, you’re a manager in this role, this very difficult job, and your team said, “Hey, Jesse, by the way, you’re the youngest guy in this room right now, and you’re in charge.”
[00:18:47] Jesse Matthews: We got back from, like, the management meetings and they were patiently waiting, of course, to hit the phones and they go, “Hey, we figured something out.
[00:18:55] Like, how old are you again? When’s your birthday?” And I think I missed it by, like, a month. One of the guys goes, “We’re all older than you.” “Okay, great. That should be motivation to you, one, but also,” uh, yeah, it’s definitely, it was an interesting experience, but I loved it.
[00:19:13] Marc Gonyea: But, what’s your take on that? Like, what did that teach you?
[00:19:15] What’d you learn from that as your perspective shifted?
[00:19:18] Jesse Matthews: I guess kind of everybody has their own path that they’re going through. I had a couple of guys, one that we talked about a little bit earlier, Mapper and Felt, He was awesome. He was one that hit the phones immediately.
[00:19:29] It was just a killer, but he did the whole Capitol Hill thing, didn’t love, and ended up saying, “I want to get into something else.” He came through the interview process and I remember, I forget who interviewed him with me, but they really grilled him way more than anybody else to make sure he was a good fit,
[00:19:47] and he ended up getting hired, crushing it. But yeah, I think during the DM process it was really figuring out how to manage a lot of different personalities that aren’t the same as you, I guess, the easiest way to put it, right?
[00:20:01] Marc Gonyea: Yeah, for sure, and manage the clients, right? Like, that’s another thing,
[00:20:06] so you got to work with the, your colleagues or former colleagues. That’s another weird thing, too. You go from being a peer to being the manager in a job that has a high degree of accountability. It’s not like a job where you’re just kind of a team lead. Like, you’re responsible for their production, at least that’s how the client and I looked at it back then.
[00:20:25] So, what happened? ‘Cause then you had, was ThreatConnect your client? While you were managing them.? Yeah. So, like, what, so what kind of evolve? How did that evolve?
[00:20:35] Jesse Matthews: So, I guess walking through the process there, I was managing ThreatConnect. I had been a DM for about a year at that point, and I remembered thinking, I got to the point about eight or nine months in,
[00:20:50] I remember both of you guys telling me it’s going to take nine months at least until you feel comfortable in the job, so I felt comfortable on the client calls, I felt comfortable with everything else, but I kind of thought, “I don’t know if this is what I want to be doing right now,” kind of really just felt like I wanted to go back and be an individual contributor, do my own thing,
[00:21:10] worry about my own quota, whatever it is that I have to do. So, I ended up making the decision, “Hey, I want to go back to being maybe an SDR or an AE, whatever I could do,” and Threat Connect was one that they were looking for somebody. I’d talked to Kristen, talked to you guys and said, “Hey, how can I leave?
[00:21:28] Potentially leave memoryBlue. Went on a good note.
[00:21:31] Marc Gonyea: Gracefully. Yeah. You put your time in and then how did, so ThreatConnect at the time, that’s Christine Schaefer, right? God bless her.
[00:21:39] She’s amazing.
[00:21:40] Marc Gonyea: She’s amazing. She’s a great memoryBlue supporter and fan, she’s the first person that ever said Captain America to, try to make that stick with you for your entire career.
[00:21:51] Yeah, definitely did. So, let’s talk about that, so then, everyone thinks their career should be, like, a linear, but you had gone from SDR to delivery manager, then get a ThreatConnect, you said, “Okay. I’m going to go back to being an SDR for a little bit.” Talk about that ’cause lot of people don’t have that self-awareness and maturity.
[00:22:12] Jesse Matthews: Yeah, for me it wasn’t that hard of a decision because for me, I got to the management level, I learned a lot, kind of took that step up, but it wasn’t like I was typically taking a step down in that path, I was just going back to another path and kind of starting over. So, I never really looked at it as a negative.
[00:22:30] Actually, one thing Christine kind of pitched was being a team lead or a team lead slash player, which I told her, “I just want to go back to individual conversation.”
[00:22:40] Marc Gonyea: You and I talked about that. And then, how did that go? So you shook her off.
[00:22:45] Jesse Matthews: I just want to be AE. That’s another branch where I’m potentially going back into the management.
[00:22:53] And like, I said I’m 20, I think I was 23. I want to do my own thing for a little bit.
[00:23:00] Marc Gonyea: And not in a bad way. By myself, and you have to go singularity of focus and how, like, if you really want to get to that path of being a closer, make that, put the word on the street. Yep. “I’m here to be a closer and I’ll do what the company needs to be to do, what’s right,
[00:23:20] but if you can find someone else for that position or for that role, I’ll support them as in my own role.” I remember we talked about that ’cause that was a bit unique of an approach, right? Because most people kind of fall in that team lead trap. Not that it’s a trap, but just, you said not to, you shook that off, but still use back in the SDR role.
[00:23:41] Jesse Matthews: It was fine. The one thing also, when I finally made the decision, “Hey, I don’t want to be a DM. What can I do here?” One thing, when I was going back into the interview process, I don’t think I actually really interviewed, but you guys made it very clear, “Go somewhere where there is a path.” Yeah, and the couple people that had already paved the way there was Cat Doulis and Ben Yonak. They’ll be really pleased I gave them shout-out, but yeah, they had gone through the path.
[00:24:10] They were BDRs there, Christine took them in and at that point they were already up to what we called the ISR role. Yep, exactly. So, I knew what I was getting into, I knew it could be fast and it was, like, four months before I was sitting in a different seat within ThreatConnect, which is cool.
[00:24:27] Chris Corcoran: That’s great.
[00:24:28] That’s great. What did
[00:24:29] they do?
[00:24:30] Jesse Matthews: So they were a tip, a threat intelligence platform.
[00:24:33] Chris Corcoran: Okay. I gotcha. So, were you, was that part of your decision process? ” I want to get into cyber or I want to focus on cyber?” As a DM, one of the things I think is a valuable part of that role is that you get exposed to so many different technologies and sales cultures and having that nine months a year of that experience,
[00:24:52] were you gravitating towards cyber or talk a little bit about yeah, that?
[00:24:56] Jesse Matthews: For me it definitely was cyber. So, I had a couple different clients. I think the one that stands out in my head was Nehemiah Security which actually is a part of ThreatConnect now I believe. So, they got bought out, I think, by ThreatConnect..
[00:25:10] So, for whatever reason cyber just interested in me, and when you’re a BDR, there’s a lot of different things that you can go into, right? And the tech industry, you’ve got basic IT, storage, cyber, whatever the case may be, so I figured I might as well sell something that gets my attention and it’s growing at a rapid pace.
[00:25:30] Marc Gonyea: Jesse. Cyber’s so hard. My success is if I have a good client and nobody picks up the phone, cyber in the desk, these guys are so paranoid and, like, they’ll pick up the phone, cyber’s so competitive. That’s, that’s, like, me doing, like, my whiny, you know, I’m having a bad day at the office, SDR role, and my retort is you want to be in cyber
[00:25:53] ’cause it’s so competitive and so hard to get these people on the phone. So, can you, for the audience, because they’re not going to listen to Chris and I, understand I’ll do so, why do you want to be in cyber if you’re an SDR? You kind of said it but, like, this says hit, this, hit it right between
[00:26:07] the nose.
[00:26:08] Jesse Matthews: There’s just an insane amount of companies that start every single day, but one of the companies that I went to was a startup with incredible technology. So, the growth is there. You need to talk about, like, data is growing and a couple of years from now it’s going to be 90% greater, 190% greater or something like that than what it was 10 years ago.
[00:26:27] And cyber is the same, like, threat actors are only getting better at getting into networks and moving laterally and doing whatever. So, to me it was an exploding fields and it got my attention. There were so many things that you can do within just the niche of cyber, so many different areas. Like, you guys know, like, SOC threat intelligence, security operations, things like that.
[00:26:49] Marc Gonyea: It’s just because there’s a ton of opportunity.
[00:26:51] Jesse Matthews: Exactly. Opportunity in a nutshell.
[00:26:53] Marc Gonyea: The same reason that it makes it so difficult is what, is where the opportunity lies. So, you would, the ThreatConnect, learned more about the technology in the space, what did you have to kind of learn and develop to get to that next role though?
[00:27:05] You can’t just like, it’s not this like, some people think, “I’m going to be an SDR for six months, then will get promoted. I wanna be an SDR for nine months or a year,” how did that happen?
[00:27:14] Jesse Matthews: I think, for me in that particular BDR role, because a lot of it was inbound. We did, I worked with actually Brendan Andrews,
[00:27:23] he was another rep. He, finally, towards the end of my, it was only four months, but gave me some of his accounts, So it was not just going from inbound and booking the meetings where somebody is requesting a free account or whatever the case may be, was working with Brendan and I actually got a couple meetings with his prospects,
[00:27:42] he kind of walked me through a way he did, who I needed to target and I think I proved, “Hey, I can generate my own meetings that are good meetings,” that the AEs are actually going to be able to take into opportunities and potentially close down the line, and that was the big difference. I think that’s why they ended up giving me a shot to work with an outside rep in the Northeast territory, which was the largest territory by far pretty much.
[00:28:06] Marc Gonyea: And what did you do? What was the next role when you got moved up?
[00:28:10] Jesse Matthews: It’s definitely an interesting one. We called it an ISR. So, basically you’re part of the 90% of the full sales cycle. You have an enterprise rep that you support, so you’re booking your own meetings in, like, a top 250 accounts scenario, and then you’re on the demo,
[00:28:28] you’re working with them during the POC process. You’re kind of working hand-in-hand on a daily basis, but usually when it gets to legal signatures, that, the tougher part of the deal, validating that, crossing the T’s, whatever the case may be, that’s when they would take it full-steam, and then your job is just to generate more opportunities for them to clubs.
[00:28:46] Marc Gonyea: All right. And then you’re
[00:28:47] learning things about the sales cycle along the way. So, it’s just not going in the meeting and turning it over, it’s, so would you consider yourself closing in that role?
[00:28:57] Jesse Matthews: I didn’t. No.
[00:28:58] Marc Gonyea: Okay. All right, which is okay, right? So then you’re learning the next set of muscles to develop.
[00:29:04] Is there anything in that role in particular was most eyeopening to you or more interesting or something that you go, “I gotta work on this?”
[00:29:12] Jesse Matthews: Actually, outside rep, and the biggest thing that he taught me probably was picking your opportunities because as a salesperson, you want to think that you can close every deal, but that’s just not realistic,
[00:29:27] so it’s picking the ones that you know are good from the get-go and working on those and devoting time to them, because if you’re taking meetings that are the S for lack of a better term, you’re just gonna be wasting your time, right, and then you’re not going to close as much as a consequence of that.
[00:29:45] Marc Gonyea: What do you look for?
[00:29:46] So, how do you do that? Because that would kind of freak me out if I’ve got to have this quota you got to hit, and it’s kind of you as to where you spend your time, and I’m just going to tell you, “Hey, this deal is going to close.” What do you look for in an opportunity was being cultivated or even the early stages to know whether or not you want to spend your most high blast that on?
[00:30:03] Jesse Matthews: It goes back to, I don’t necessarily follow it to a T, but the BANT – budget, authority, need, timeline,
[00:30:09] so whenever I have an intro call at the very end, the always, the thing I always ask is timeline. “Is this a project that you’re actually working on or are you just gathering information?” And then from there, if they’re just gathering information I’ll kind of say, “Hey, I can provide you with more,” and leave it up to them.
[00:30:28] Like, “You let me know what you want to do next.” A lot of times if it’s not a great opportunity they’ll say, “Hey, a month from now shoot me a note.” If it’s a good one, they’ll want next steps. So, you’re never trying to sell them. At some point, they’re almost selling you on why they need the solution.
[00:30:44] Marc Gonyea: Interesting. Okay. And then, at that point you decide if you’re going to invest more cycles.
[00:30:48] Jesse Matthews: Exactly.
[00:30:49] Marc Gonyea: In that role, did the rep that you worked at Northeast, did he have a sales engineer he worked with,? He did. What’d you learn about working with those people? ‘Cause if you’re an SDR, you don’t work with sales
[00:30:58] engineers.
[00:30:58] Jesse Matthews: No, I was an SDR, so that was definitely an experience because, again, I almost think being a DM helped with that because SEs, they’re great, they’re super technical. Not all of them have the sales acumen, a really, really good ones do where super personable on the phones, right, as you guys know, but some of them are a little awkward and you kind of have to manage them on the calls.
[00:32:21] You have to say, “Hey, Mr. Prospect, Mrs. Prospect, is all of this making sense? Is there anything we’re missing?” ‘Cause sometimes they’ll go through and just rapid fire all of the technical aspects of it and it gets to the end and the team is silent and you have no feedback during any of it,
[00:32:37] right?
[00:32:39] Marc Gonyea: So, you have to manage the prospect during the cycle and kind of size them up, evaluate how interested they are,
[00:32:45] but then you also times there seem, and Aspen’s a prospect, right? Certain prospects will judge differently with certain SEs, but you kind of have to make sure your, your SEs dialed in too, so you gotta navigate that, when to jump in and not to jump in, maybe they’re going down the rabbit hole, but you don’t want to go down, because they’re excited about, ’cause they think it’s cool, but they may not know that the prospect, they don’t care about that.
[00:33:06] Jesse Matthews: Yeah. And
[00:33:07] some of them, some of the prospects, they’ll sit there for an hour and not say anything and they’ll get done, and they’ll say, “That was incredible,” and then there are some that they’ll go through and they’ll ask every question they can think of under the sun, so it’s not necessarily indicative if they’re engaged or not during the middle process, but usually it’s just better if you can get live feedback during it and can pivot from there as opposed to waiting till the end,
[00:33:33] and then you missed a shot to potentially talk about something else, right?
[00:33:35] Marc Gonyea: Yeah. How long was the sales cycle, typically, at ThreatConnect?
[00:33:41] Jesse Matthews: I would say at least six months, probably six to nine because of the size of the companies, one that we were working with and this solution’s really in-depth and it usually entail the proof of concept and their environment, which took three months alone,
[00:33:57] I would say.
[00:33:58] Marc Gonyea: How involved with those were you?
[00:33:59] Jesse Matthews: Decently. It really would depend on my time, how many opportunities we had, and I think I gained the trust of my outside rep at some point, and he let me sit in on those meetings or even run some of them if we were double-booked or something.
[00:34:14] Marc Gonyea: Wow. Okay. And that’s just the tool and the environment,
[00:34:19] and then, was that usually, was there a competition involved? Would they do a proof of concept with you guys and someone else? Bake off? Who were you guys most commonly baking off against?
[00:34:27] Jesse Matthews: Anomaly and then, the second one, Yeah.
[00:34:32] Marc Gonyea: Local.
[00:34:33] Jesse Matthews: Exactly.
[00:34:33] Marc Gonyea: Local client or local competitor? Okay. So you do this POC and then what when all will come out in the wash, it was, like, the average size of the deals over there?
[00:34:42] Jesse Matthews: I would say probably around 150,000 or so.
[00:34:46] Marc Gonyea: Okay, nice. And then, how many did the rep have, their number?
[00:34:52] Jesse Matthews: I think quota at one point was 1.6 and then got upgraded to 2 million or so, but usually there was a couple really large deals in there. I would say, like, 500K+ or more than that. Yes.
[00:35:07] Marc Gonyea: Okay. Okay.
[00:35:08] So, if you were just doing our 50 K deal, you have to do 11 deals, but if you’re doing big deals, maybe do, like, five or six.
[00:35:13] Jesse Matthews: Yeah.
[00:35:14] I know of one team at one point that did one deal and hit quota.
[00:35:19] Marc Gonyea: Wow. Yeah, that must have been nice.
[00:35:21] Jesse Matthews: Yes.
[00:35:22] It wasn’t me.
[00:35:23] Marc Gonyea: I’m not that guy either. Alright. So, when this is going on, I guess my final question would be, when you were in that kind of role, it’s like a team selling role, right? How are you paid?
[00:35:35] Like, generally speaking, because people will talk about this, both sounds really cool. It’s a great way to learn. How would you get to, you’re helping with these POCs and moving things along, are you tied to, like, the size of the deal or what?
[00:35:48] Jesse Matthews: Yeah, exactly. So, for us, I mean, we had kind of a meeting number that we had to hit for our outside rep, but we weren’t paid on them.
[00:35:59] Marc Gonyea: Base salary.
[00:35:59] Jesse Matthews: Exactly. So, we were just paid on whatever our outside rep closed, so it was great, the guy who was the VP of Sales there at the time was John Lyons and he was the one that really stressed that methodology, which I loved. The only thing that can not be so great is if you’re outside rap is not the best.
[00:36:19] You’re getting paid on that commission. I was very fortunate where mine was, but at the end of the day, you’re still learning. So, it was fun.
[00:36:26] Chris Corcoran: Okay. That’s great. Does he live in the Northeast or was he local?
[00:36:29] Jesse Matthews: He lives in New York.
[00:36:30] Chris Corcoran: He lives in New York. Okay. Gotcha. Now, were you ever able to go on, like, field calls?
[00:36:34] Jesse Matthews: No, never did. I actually only met him once every year and
[00:36:40] a
[00:36:40] half, maybe.
[00:36:40] Chris Corcoran: Okay. How long did he do that role before he got moved up?
[00:36:44] Jesse Matthews: I think, I think it was a year plus. We worked together for maybe a year and four months or so before I ended up going over to Inky.
[00:36:51] Chris Corcoran: Talk about
[00:36:54] that.
[00:36:55] So, we went through kind of a transition period at ThreatConnect where in sales things get shook up, maybe you’re not so happy about them, whatever the case may be, so I thought, “You know what? At this point I’ve learned a ton from my outside rep.” He kind of agreed. Yeah. I think you keep playing more of the mid-market space, maybe not enterprise yet,
[00:37:14] Jesse Matthews: so I went over to Inky where John, who I considered kind of a mentor, he’s the VP of Sales, he had just gone to become the CRO, so I went there as a mid-market rep.
[00:37:24] Chris Corcoran: And so, you follow the VP of Sales who left to go to a different company? You followed him?
[00:37:30] Essentially.
[00:37:31] Jesse Matthews: Essentially.
[00:37:32] Marc Gonyea: Very cool. If you think about too, he had been working with ThreatConnect for over two years.
[00:37:37] I think I was out, like, a year and 10, maybe.
[00:37:39] Marc Gonyea: I’m taking into account the memoryBlue. Yeah. So, I always, people always forget about that, but I’m like, no, if you’ve worked with them, you work at memoryBlue, but you’re familiar with that company. So, you’ve been there for a while or working with them for a while, I guess, and then
[00:37:50] John, well, that’s very important. I kind of did that too, like, my first job out of school ever talking about Andres Beebe, he was a salesman, was my direct manager, but I saw him operate enough I know I want to work for him. He went with the best within the company. There’s a lot to be said for that. So, but also, what else did you think about though when you left?
[00:38:07] Like, did you look at the, it sounds like you’re in the side bridge to look at the tech of the company before, this is a question for you. Like, when you’re an SDR, you’re not becoming your career, you still are young man, what do you look at? How do you size up the company or the market attack?
[00:38:21] Jesse Matthews: Yeah, so, again, like, the one thing about ThreatConnect that was great is I got exposed to a lot of different cyber technology, basically they just aggregated a bunch of technology together in their platform. So, I kind of knew at the time what was a hot topic and what wasn’t. So, phishing emails was something that was, which is phenomenal
[00:38:40] from a sales standpoint. I think 90% of times were privileged credentials get compromised it’s from a phishing email where somebody clicks on something. So I knew this base was hot, and then the CEO of the company or founder had a track record. He sold his last company, it was ITA software, which was basically this platform that would take in all of the flights that you could more easily booked them, which now is Google Flights.
[00:39:07] If you’ve ever used that, his company was the one that had all of the tech and a cop out for, like, $800 million or something like that, so.
[00:39:14] Marc Gonyea: Those guys with glasses on the table.
[00:39:17] Jesse Matthews: He was awesome though. I met him the first day. He talked to us and he’s super technical guy, but talk to, like, he knew where you were coming from, you know, as a sales guy, he wasn’t trying to be the smartest person in the room,
[00:39:29] like he was.
[00:39:30] Chris Corcoran: ‘Cause he already knew he was.
[00:39:31] Jesse Matthews: Yeah, exactly. Exactly. So, kind of that process. And then also talking with John during the interview process. He actually never interviewed me, he just gave me his 2 cents on why he went there, which really helped in my decision-making, talk him through, working in the startup.
[00:39:48] He was very clear though, “This is going to be different for you.” I was the 25th employee. He said, “There’s not going to be as many resources. You’re going to have to learn a lot on the fly like we’re all going to have to learn.” So it was kind of just weighing the pros and cons of that versus where the space was in the phishing email security space.
[00:40:06] Chris Corcoran: Interesting. And so, what’d you find, how different was it from your prior stop? Like, what were the differences?
[00:40:12] Jesse Matthews: It was smaller. There were, like I said, there weren’t as many resources.
[00:40:15] Chris Corcoran: What do you mean by the resources? I want the listeners to
[00:40:17] really understand
[00:40:19] what you had versus what you didn’t have and what you may have taken for
[00:40:22] granted.
[00:40:23] Jesse Matthews: Okay. So, number one is leads,
[00:40:30] which are great if you have them, if you don’t, you have to learn how to make your own, which is why being an SDR, I think, is always great to start at, ’cause you learn how to generate your own opportunities. But, you go from a well-oiled machine with Christine Schaffer, she’s got her full marketing team wrapped in, ramped up,
[00:40:49] we’re getting a ton of leads per day. Not all of them, right, are closing, so stuff like that. But, going to start up, you don’t have that recognition, right? So, you don’t have those leads coming in. And also, though, when you’re working on deals, the prospects, they need information, especially at security companies, right?
[00:41:06] You have to have, like, a SOC2, you have to be ISO-compliant, all of those things, which at ThreatConnect, you hit up one person, they’re like, “Here you go, here you go,” and you can just send them out email on it’s easy. Inky, it’s a lot more of do-it-yourself, create the PowerPoint that you’re going to present to the executor, whoever it is.
[00:41:25] So, you definitely take it for granted, even though ThreatConnect was by all means, like, a tier-2 startup, I would say. They only have, like, 150 people, so I had to put together, like, a 30-page RFP at one point, but I was pulling stuff together. If I had to do that at Inky, it would have been impossible, basically.
[00:41:42] It was tough. It was a learning curve.
[00:41:43] Chris Corcoran: Yeah. Interesting. Was that, but did sound like John shared that that was going to be the situation?
[00:41:50] Jesse Matthews: He did. Yeah. He was pretty clear with it.
[00:41:51] Chris Corcoran: Okay. And so, you, you were in AE role and there, so talk a little bit about how that was different than from an ISR role?
[00:41:58] Jesse Matthews: Yeah.
[00:41:58] Getting the deal over the finish line from that POC or technical win to actual signature process is definitely, sometimes that’s 50% of the deal even though on paper it only looks like 20, right? So, it was definitely tough to learn because from a qualifying perspective that’s when the timeline comes into place.
[00:42:20] That’s when the budget comes into place. When you’re an SDR you can get a really good meeting that might not have some of those things that still become something that’s great down the line. When you’re in AE, you really want to be spending your time like I mentioned earlier on the ones that are active projects that do have potential to close because that’s how you’re going to hit your number.
[00:42:40] So, it was tough to learn, for sure.
[00:42:42] Marc Gonyea: What was your, did you have a territory?
[00:42:45] Jesse Matthews: Was at mid-Atlantic, technically Virginia, Maryland, West Virginia, and then I did work on the fed, which was kind of a bus, to be honest with you. It was tough to play.
[00:42:56] Marc Gonyea: That’s a lot of work. Yeah. I suppose, especially for an emerging company, it’s company being the first fed person or one of the first people, but that’s a long road.
[00:43:04] Jesse Matthews: Yeah. There was a learning curve also just from a technical standpoint. You have to hit some check boxes to work with the federal government and we weren’t there yet, so.
[00:43:14] Marc Gonyea: That’s a problem. So being back in this world, did you have to unleash your outbound skills?
[00:43:19] Jesse Matthews: A hundred percent.
[00:43:20] Marc Gonyea: A hundred percent. So, how did you approach your territory?
[00:43:24] Jesse Matthews: So basically I broke it down, obviously top accounts first, initially I cut my teeth on some of the lesser accounts that maybe weren’t as fruitful or couldn’t be as fruitful as John likes to say, he says, “Cut your teeth,” that way you can mess up on the phone a few times when you’re giving your pitch, when you’re cold-calling somebody and you won’t do any damage.
[00:43:44] But then, from there, once I got my feet wet, it was definitely trying to tackle some of the larger accounts in my territory.
[00:43:51] Marc Gonyea: So, you’re trying to take down larger accounts and you’re selling technology nobody’s, the technology they’ve heard it, but no one’s ever heard of Inky, right? So, how was that?
[00:43:59] Jesse Matthews: It
[00:43:59] was interesting. Yeah, in terms of getting meetings, it actually wasn’t terrible, there was a couple of things that we would focus on the elevator pitch, some pains that really rang true for most folks. Really, the problem is that we were going up against the proof points, mind casts, barracudas of the world or large names and we weren’t really going to replace them,
[00:44:22] We were more so going to add on, so to be honest with you, during the pandemic, it was a really tough sell ’cause they already had a solution in place that technically worked and nobody was really buying it, right? The pandemic was tough.
[00:44:38] Jesse Matthews: Yeah.
[00:44:39] Marc Gonyea: Right, because you’re selling and you’re selling at a startup. It sounds like your songs on some of that is nice to have, but I already got some, kind of like it.
[00:44:46] So the people who might be only showing their wallets back then, that’s when people thought they were gonna turn into zombies, people were worried about the jobs. So, I mean, I guess from that standpoint, it’s like, you always hear about stuff like consumer confidence and those things, it’s the same sort of thing,
[00:45:00] like corporate confidence. I mean, people who are in this business maybe, but I get it. I don’t know, like, they’re less likely to try new stuff.
[00:45:07] Jesse Matthews: A hundred percent. I remember that probably the most notable meeting I got there was with Wendy’s, fast food chain, and I talked to the guy there who managed their Proofpoint instance,
[00:45:17] I gave the whole presentation, my SE gave her demo and she did a really great job. He said, “Look, I can see the value here, but at the end of the day proof points working enough, it’s covering the bases, so I can’t really see pitching this to my leadership and going from there without more of a need here,” because it was like 0.7% of emails were missed by Proofpoint, which at a Wendy’s, right,
[00:45:44] ends up being, like, a hundred thousand plus emails per year when you think about it, but at the time, and he was like, “Eh, it’s good enough.” So, it was a tough pill to swallow going back to my manager and saying, “Yeah, they’re not moving forward with anything.”
[00:45:57] Marc Gonyea: Interesting.
[00:45:58] Chris Corcoran: Wow.
[00:46:00] Wow. So, you’re getting into the closing role right here,
[00:46:04] you’re bringing deals across the finish line, what’s your biggest win or favorite deal?
[00:46:10] Jesse Matthews: Favorite deal, and it was, at the time it was the largest deal, it was only around 40 K, but like I said, we were in the mid-market and Inky wasn’t that super.
[00:46:18] Marc Gonyea: That’s huge, man. Our first deal was $5,000, right? It was
[00:46:25] the biggest deal.
[00:46:26] Jesse Matthews: Oh, that was my first, it was 3 K. It was a hundred users, 3 K,
[00:46:31] the biggest one that I had, it was the first time I worked different start to finish, POC, ran through start to finish.
[00:46:40] Chris Corcoran: Leave the names out of it, but just give us, tell us about the deal.
[00:46:43] Jesse Matthews: We, it was competitive. We were going up against each other.
[00:46:46] Chris Corcoran: Did you find it in prospecting or? Like, I want to hear all about it.
[00:46:48] Jesse Matthews: Okay. Yeah. From start to finish, we did not use anything at the time, like Outreach or SalesLoft that’s going to help shoot out a bunch of emails for you, so we just did the old-fashioned way with, like, a Excel document or Word document where you’re going through Outlook and you’re doing.
[00:47:02] Marc Gonyea: That looks like self party.
[00:47:04] Jesse Matthews: Yeah, exactly. So, we did that way. We had a few emails that we would send out and on the third email, the last one that I was sending out, actually the dude’s bit and he said, “Hey, this is something I’m interested in. It’s like, we have Proofpoint now and they’re not catching as much as we would like.” And then get into that intro call, turns out that they had a phishing email that somebody clicked, nothing happens,
[00:47:28] I don’t think they were breached at all. They’re able to kind of contain it at the moment, but he said, “Yeah, that’s not gonna fly with the rest of the company.” He’s now going to look at something else. So, then we hopped into the demo, my SE again crushed it. It was great. They wanted to do a POC from that standpoint,
[00:47:44] and they were POCing one other company who I can’t remember exactly who it was because it went through that process, and then the worst part is, he went dark for about two months.
[00:47:53] Chris Corcoran: So, you got a proof of concept going in, it’s a competitive bake-off essentially, and how long was the proof of concept?
[00:47:59] Jesse Matthews: So, the proof of concept was about a month which he was engaged in.
[00:48:02] Chris Corcoran: He was
[00:48:02] engaged, but at the end of the month, you’re like, “Hey, do you want this?” And he goes dark for two months?
[00:48:07] Jesse Matthews: Yeah. So, we were going, we had a plan. I think the demo was in April and we, I knew he needed to buy by June, so I think it was end of May or so came around or beginning of May and he just goes dark.
[00:48:23] Chris Corcoran: Did you know whether or not you won or lost?
[00:48:26] Jesse Matthews: That part he had given me the tactical win.
[00:48:28] Chris Corcoran: So he said, “You guys won.”
[00:48:29] Jesse Matthews: Yeah. Okay. Yeah. If I was on the phone with him, and it goes dark completely.
[00:48:32] Chris Corcoran: Oh man. Which went well, went over well in forecasting reviews.
[00:48:38] Jesse Matthews: Yeah. It was great. Yeah. It was phenomenal.
[00:48:42] It was terrible. “Have you gotten a hold of them yet?” “No.” The next day, “Did he pick up?” “No.” “Well, what do you think happened?” “I don’t know.” But that’s the worst response you can give, I think, in sales is, “I don’t know.”
[00:48:57] Chris Corcoran: So, keep going. Eventually the guy surfaces?
[00:48:59] Jesse Matthews: Eventually surfaced. Pandemic stuff. He had more employees than needed to go remote,
[00:49:05] he had to manage all of that. I think he mentioned something happened with one of his kids as well. Completely understandable. I know everybody likes to think, “They would call me back if they were either not going to purchase or they were going to, it’s only one phone call,” but the reality is that doesn’t happen all the time.
[00:49:20] So eventually he, I think he shot me a note back or maybe I got him on the phone again and he’s like, “No, no. Like, June is still it.” This was, like, two weeks to go in the quarter, so then it was, like, a hard push to the finish line to get the, I think you, to get the pricing down.
[00:49:35] Jesse Matthews: Everything else, the signature which might be, a few sales was awesome. Her name was Carlene, and she was, like, step-by-step because she had jumped in earlier when he wasn’t responding and did the all-move where she shot him a note, get some power in there and try to get a response, and it didn’t work at the time, but.
[00:49:52] Chris Corcoran: So, but ultimately the end of this, the deal ended up closing and it was June deal,
[00:49:55] Q2 deal?
[00:49:56] Jesse Matthews: Yep.
[00:49:57] Marc Gonyea: Awesome. It was great that people start paying them money.
[00:50:01] Chris Corcoran: Yeah. So, why is that your favorite?
[00:50:04] Jesse Matthews: I think just, from start to finish, it was mine, that I worked, and my VP did get involved, but for the most part she maybe sent a couple emails at the end.
[00:50:14] Chris Corcoran: That kind of stuff happens all the
[00:50:15] time.
[00:50:15] Jesse Matthews: Yeah, exactly. So, signature is all that stuff, but I think just because of start to fruition I found it first of all which was great. Yeah. And it was the largest one at the time that I closed. I knocked out a couple of, like, 3 K, 10 K at the time, but wanted to get kind of a bigger fish.
[00:50:32] Chris Corcoran: I got you. How about
[00:50:34] your, the one that got away, kind of the loss that
[00:50:37] haunts you?
[00:50:39] Jesse Matthews: So, I won’t say what company was it, I don’t know what specifics I can give, but it was working with Mass Mutual, obviously is a huge company, and I had the relationship with the director of InfoSec. So, I called him, basically tackled this guy for a long time, and he finally said, “Look, I’m not moving forward. I’ll reach out to you when I need something,”
[00:51:02] which as a salesperson, it’s like one of the worst responses ’cause then you go, “No, I want to book something with you. Get some time on the calendar at some point.” Two months later, though, he comes back and he sends me an email specifically and he says, “We’re ready to move forward. Let’s get.” And we do. It’s a competitive deal, a bake-off and we ended up just not getting it done.
[00:51:27] He just kind of dropped the ball, to be honest with you, and it should have been a deal that we should have while we lost to a competitor who was not up to par with our solution, and the writing was on the wall, the guy even said like, “Look, you guys were kind of the person we were going with, to be honest with you.
[00:51:44] We just brought the other guy in as a checkbox, but then we dropped the ball and they picked it up and they did what they could,” they didn’t do as much as we could, but they did it well and they did it right and they got the win. This could have been a 300 K. So, what did,
[00:51:59] Chris Corcoran: and what did that, I obviously, I can see why it haunts you,
[00:52:02] and a lot of times salespeople will say, “Well, listen. I did my job,” right? So what did you learn from that experience?
[00:52:08] Jesse Matthews: I think that was one where from a resource standpoint, from an SE standpoint, as a resource, she had a lot that was going on. She was a great SE but her family was over in India and she actually spent time there during the POC process.
[00:52:22] So, that was one of the things that threw a wrench in there, and it probably would have been good from the start to assign somebody else to that because she just wasn’t up to the task, understandably, so it was, she was dealing with, I forget there was like flooding there, with her family, so she went over.
[00:52:40] So, from a SE resource perspective, we just got off on the wrong foot. If we had brought in somebody else, they probably could have crushed it. There’s 300 K for the business, right?
[00:52:50] Chris Corcoran: Wow. Yeah. I can see why that haunts you.
[00:52:52] Jesse Matthews: Yeah, for sure.
[00:52:53] Chris Corcoran: Okay.
[00:52:54] Marc Gonyea: Gotcha. So you’re at Inky, so you’re doing the early-stage startup thing.
[00:52:59] There are ups and downs, right? I’m a big believer that the early part of your career is all about learning, right? Getting some success, which you clearly had, but the reality too, is there are opportunities for people with those talents. So, you ended up leaving Inky at some point, right? And then, how’d you size up what you wanted to do next?
[00:53:18] Jesse Matthews: Again, it all comes down to, for me, the clear path, knowing people that are at the other organization and having success. So, there’s kind of the framework that you can just pick up. So, Kat Doulis, who I already mentioned, her now fiance worked at Thycotic and ironically, John Lyons, who was the CRO at Inky knew one of the managers who was looking for a job
[00:53:42] and he was the one that said, “Hey, Jesse’s in the market. Why don’t you take a look?” So it was kind of a tandem thing. Brendan Andrews is also there, John Paul Francoise is there. JPF, yup. He’s on my team now.
[00:53:58] I know. He left. He went to Higher Logic.
[00:54:05] Jesse Matthews: We all blend together. So yeah, it was kind of a perfect storm. The interview process was pretty quick. Ben had just, he was finishing and they were offering him, there were two spots on my former manager, Jeff Power’s team, and Jack recommended me, John recommended me to interview, process was super quick, got in the door and the rest is history.
[00:54:26] Marc Gonyea: What do they do?
[00:54:27] Jesse Matthews: There are privileged access management.
[00:54:29] Marc Gonyea: Privileged access management. Is that
[00:54:32] password management? Is that role-based security or what is? I don’t know anything about cyber, so.
[00:54:36] Jesse Matthews: Pam.
[00:54:37] Marc Gonyea: Yep. That’s very good. Tell me more, Jesse, please.
[00:54:39] Jesse Matthews: Pam spray. No. Pam is actually what I say, and some people will actually go, “Yeah, Pam.”
[00:54:44] Yeah. When they don’t, that’s when you’re like, “Okay, you don’t really know what’s going on here, so let me explain it.” But it’s all encompassing. So, you actually hit the nail on the head. It’s password vaulting, it’s also role-based access control. So, it’s taking privileged credentials wherever they are, and making sure you secure how they’re accessed and who can access them because that’s the number-one thing,
[00:55:06] it was, AIG put out a report last year that 99% of ransomware attacks were because somebody got hold of credentials that weren’t locked down and were able to get money from some of the big fish in the world.
[00:55:18] Marc Gonyea: Okay. And you’re selling now? Continue to sell, excuse me, And then who you selling to?
[00:55:23] Jesse Matthews: So, for me, I’m mid-market. I’m actually just New York. Thycotic is a little bit more of an established company that got a lot more reps, so I’m just just in the New York area and it’s actually, I’m splitting it with three other or two other reps.
[00:55:37] Chris Corcoran: Excellent. How
[00:55:38] do you split? By company name or is it three field within the geo?
[00:55:42] Jesse Matthews: Company name.
[00:55:42] So, I’ve got G through O.
[00:55:44] Chris Corcoran: G through O.
[00:55:46] Marc Gonyea: Yeah, that’s great. Yeah. New York City, New York City? Oh, wow. Okay. No, that’s great. Yeah, it’s ton of the commerce out there, and then what are the days and nights like?
[00:55:57] Jesse Matthews: Days and nights like? So, it’s similar to Inky. I would say though, the best thing about Thycotic is that this is a need to have,
[00:56:06] and one of the things that my manager said when I was interviewing really stood out to me, he said, “We didn’t take any sort of dip during the pandemic because everybody went to work remote, companies had to secure remote access to all of their information.” So Thycotic, I think, hit, like, 105% of their yearly goal, even during a pandemic.
[00:56:26] So, it’s definitely a need to have, I mean, it’s great. There’s a lot more inbound lanes about people who are just genuinely interested. They have budgeted projects, but there’s definitely, we have a lot of metrics that we have to hit. It’s a super metrics-oriented company, but in a good way, right, it’s always filling up your pipeline so that when deals do drop, one’s there to jump right in place.
[00:56:49] Marc Gonyea: When you experienced that,
[00:56:51] it’s like, we had the insurance, you don’t buy insurance until you need it. Okay. So, it’s probably tough, some noise that to have a very metric-driven organization, but safety, risk, hedging. So, okay, and I think, for you, compared to a lot of people, we have, you’ve got, you’ve had, like, a unique, very educational journey along the way.
[00:57:13] For me, at memoryBlue, kind of realizing that what you wanted to do and going to work for a client who you knew, but different size company, and then go into
[00:57:20] a true startup,
[00:57:22] or early stage, Thycotic has been around a little bit longer. It was, sounds like they have an, an, a different, but even within cyber, a different market.
[00:57:29] That’s what I tell people. So, in cyber, there’s so many different little niche industries that you can benefit from them all, and, and I think the investment you’re making in cyber the past, what you’d say, five or six, six years, this it’s going to pay off the longer you’re in it. So, do you intend a plan, you planning to stay in cyber?
[00:57:48] Jesse Matthews: I haven’t really thought about going anywhere else. I think cyber is kind of where my interest lies from because when you’re a salesperson, it’s, you don’t have to understand every nuts and bolts of the technology, but for me it’s just interesting. So, I like actually learning about it, getting to know the products so that when I’m on a call, if an SE happens, and I know a question maybe I do just because you’re kind of a student of the game in cyber and there’s a lot to learn.
[00:58:14] Marc Gonyea: Yeah. And I also think nobody wants you to know what you don’t know, and having the SE, but that can help you, a lot of sales professionals prospects. Nobody likes to know it all, but you have a very genuine, sincere way about you, so I don’t think it will come across the wrong way if you try and get into the mix a little bit more with some of these folks. The average rep.
[00:58:32] Jesse Matthews: There was this guy, we call him D. Hop,
[00:58:34] his name is David Hopland. He worked at ThreatConnect and now he’s the VP there, and he could give his own demo if he wanted to. He crushed his number. His SE was awesome, but they kind of played this, like, tandem role where he would speak on things from a sales perspective while in technical terms and SE would really just come into the POC and crush it.
[00:58:54] Marc Gonyea: Yeah. And is
[00:58:55] that what you kind of aspire to go? Or you be, like, a junior version of that or?
[00:58:59] Jesse Matthews: Kind of, yeah, that’s what I’d like to be. He was super organized. He always had a plan. He took really diligent notes that every call that he hopped on he was prepped, he knew what he was going to cover specifically, knew what the pains were,
[00:59:10] so getting deals done for him, it wasn’t really an issue.
[00:59:14] Marc Gonyea: Wow. Okay. All right. And that’s how you try and model some of your game after that? And then, who are you selling to now? Dead market? New
[00:59:22] Jesse Matthews: York? Personas? So, it’s anywhere from the CIO, CESO down to, like, system administrators, even. Anybody who has basically a privileged credential and then network, which is anybody who is in the IT space.
[00:59:38] Marc Gonyea: You have to have a
[00:59:39] computer, obviously.
[00:59:41] Jesse Matthews: Essentially.
[00:59:42] Marc Gonyea: And then, what are people doing for it now? Are you throwing out a competitor or you, do, there’s some people using, like, something out of the box, it’s like a generic feature?
[00:59:50] Jesse Matthews: There’s a couple. So, we call them like pseudo competitors, like lastPass, right? Where they just store basic passwords. I use it at home.
[00:59:58] It’s awesome, but they don’t have a lot of the functionalities. That’s why I say pseudo. The other competitors are CyberArk and Beyond Trust are the two big ones.
[01:00:07] Chris Corcoran: They’ve been around for awhile.
[01:00:09] Jesse Matthews: They’ve been around for a long time, timer X for the IPO, but then we actually have combined or merged with one of our former competitors,
[01:00:18] Centrify. So, technically our company named now is Thycotic Centrify, which will change again in I think about two weeks or so, like that, so big announcement coming, coming there. But yeah, those are the big players in this space and we like to pride ourselves on being really the cloud-first solution.
[01:00:35] That’s how we usually get a lot of wins. Just being easier to use.
[01:00:39] Marc Gonyea: Okay. Interesting. All right. So, Jesse, knowing what you’ve gone through, where you are now, what advice would you have for yourself the night before you started memoryBlue?
[01:00:49] I think I kind of did it, just being kind of who I am, rolling with the punches, but that’s
[01:00:55] what I would really say, is, get the most out of each experience you have. So, being a DM, taking the step back, moving to the ISR role, just roll with the punches, like, have your goals in place that you want to achieve, but don’t get so focused on one thing that you don’t see the other opportunities that are around you.
[01:01:13] Chris Corcoran: Probably.
[01:01:14] Okay. All right.
[01:01:16] And Jesse, you seem like you’re more of a startup, more of a small-company type of person that you, is there anything in particular about the large companies that don’t, that don’t, that you don’t find interesting or?
[01:01:27] Jesse Matthews: Not really. I think I’ve just tried to be advantageous about where I’m going, where I already know people.
[01:01:34] Chris Corcoran: Yeah. I see.
[01:01:35] Jesse Matthews: That’s a lot of that. I mean, with Thycotic, with ThreatConnect, I already have relationships there, so I knew I could come in and grow. and a lot of the big companies I don’t, to be honest with you, plus I think that is a little bit scary, I’ll admit, to go to a big company and be somewhere where you are sometimes just a number, as opposed to even the CEO can know your name sometimes even at Thycotic, which is, like, 500 plus employees.
[01:01:57] Chris Corcoran: Yeah. Well, I
[01:01:58] mean, you’re the guy who brought in that deal from scratch, a startup.
[01:02:02] Jesse Matthews: Yeah.
[01:02:02] Chris Corcoran: That’s,
[01:02:02] that is huge versus a big company, “Who’s next?”
[01:02:06] Jesse Matthews: Exactly. For the gain, a big company is like, okay, your manager gives you a chair, get dressed and it’s like, ah, it’s okay.
[01:02:14] Marc Gonyea: I mean, obviously going back to the superpower theme, you’re really good at relationships,
[01:02:19] I feel like, right? For sure, to help you longer-term in your career. Well, think about it. So, the past, you worked at memoryBlue, you met Lions when you were working here, did you meet him when you
[01:02:28] worked at ThreatConnect?
[01:02:29] Lions, I think we’ve worked with him before, prior to work for a little while throughout Matt Bright worked with John, I believe. You’ve been moving along and you’ve got a crew of professionals you’ve worked with. The VP here, Nicky, so that’s a really good trait that I think a lot of people can learn from, because it’s easy to say,” I’m a relationship person and have relationships with people,” but another thing to actually maintain and build and carry them through companies 3, 4, 5, 6 years.
[01:02:59] Jesse Matthews: Yeah. Especially the cyber world in general, but even IT, it’s a lot smaller when you get down to it and you can surprise, I’ve met Matt Bright out in, at RSA maybe, I think, where, what’s the other one in the, Black Hat. So, I met him out there with John, actually. I’ve never met him here because he was a year or so older. Got his business card,
[01:03:19] we talked, like, once or twice, but, like, I hit him up on the line, every need a job again, he might be somebody that I could go to. Never want to burn a bridge.
[01:03:27] Marc Gonyea: So, is that, uh, is that why you’re like that? You like building relationships, not burn bridges or what? Thinking opportunisticly?
[01:03:32] Jesse Matthews: I think, yeah, just opportunistically, but also everybody usually in this
[01:03:37] world has something that they can give. Not that I’m always looking for that, and that’s why I create the relationship. I think I am just one of those salespeople, as a people person I like chatting with people and getting to know people as you guys know, but also it can pay off in the future, right?
[01:03:53] Marc Gonyea: Excellent. And we were talking before we started this thing about, a little bit about that reflection of who you are as a person.
[01:03:59] Jesse Matthews: Appreciate it.
[01:03:59] Marc Gonyea: There you go, man.
[01:04:01] Chris Corcoran: Very good, Jesse.
[01:04:01] Well, we appreciate all the wisdom.
[01:04:03] Jesse Matthews: I don’t know if I call it wisdom, but my 2 cents at least.
[01:04:05] Chris Corcoran: It’s very good. Very good.
[01:04:07] Jesse Matthews: I’m glad we could connect.
[01:04:09] Chris Corcoran: Excellent. All right, Jesse. Well, thanks a bunch.
[01:04:11] Jesse Matthews: Thank you guys. It’s been
[01:04:12] fun.
[01:04:12] Chris Corcoran: Definitely.