Episode 21: Matt Bright – Making Lemonade
Everyone has heard that old saying, “When life gives you lemons, make lemonade.”
Ever since a young age, Matt Bright has been making every deal just a little bit sweeter. Matt hails from Columbia, MD, and he attended the University of Maryland. Shortly after graduation, Matt started his rewarding sales career at memoryBlue. He decided to stay on board following his tenure as an SDR, when he ultimately became the second person to ever close new client deals for the business. Today, Matt is a successful Sales Director at Snyk and maintains close ties to memoryBlue. (In fact, his company recently completed a campaign with memoryBlue that closed with two SDRs getting hired out.)
On this episode of Tech Sales is for Hustlers, Matt Bright shares the critical importance of listening to call recordings and learning from other sales pros, details just how he sizes up startups, and why his favorite and most valued deals are self-sourced.
Full Episode Transcript
Name: Matt Bright
Title: Director of Sales
Company: Snyk
Exit Year from memoryBlue: 2014
Months at memoryBlue: 25
Alumni Path: Internal Promotion
***Introduction***
Matt Bright:
You’ll talk to somebody who’s maybe six weeks in the job and they’re like, look, this is the approach that works. And I’m like, that’s cool, but you gotta build out your repertoire. You gotta continue building out your skills. Because if you’re literally only doing this one aspect of it, that’s not setting you up for the long run.
Marc Gonyea:
This week on the podcast, we have Matt Bright Director of Sales at Snyk. Matt shares with us the importance of listening to call recordings, how he sizes up startups and why his favorite and most valued deals are self-sourced. Hi, I’m Marc Gonyea.
Chris Corcoran:
And I’m Chris Corcoran and you’re listening to Tech Sales is for Hustlers. Tech Sales is for Hustlers is a podcast where we catch up with memoryBlue alums and reminisce about their start in high tech sales with us.
Marc Gonyea:
Let’s go get some Corcoran.
Chris Corcoran:
Gonyea. You know, I’m ready,
***Episode 21: Matt Bright***
Marc Gonyea:
Matt Bright in the house.
Matt Bright:
Thanks guys. Pleasure to be here.
Chris Corcoran:
All night, Matt Bright. One of the original splash brothers.
Marc Gonyea:
So Mr. Bright, thanks for joining us. It’s great to see you. I like when everybody comes back, but I also like people who were around earlier because we have more, I guess, history together. And I was looking at things and you bounced in August of 2014, six years ago, correct?
Matt Bright:
Yeah. It’s been a while.
Marc Gonyea:
And you were with us for how long were you with us?
Matt Bright:
I was with y’all nearly two years to the day.
Marc Gonyea:
Well, wow. Alright. And you’ve done got an illustrious career since you left. So I’m going to talk about all those things today, but before we get into it, we want everybody to kind of get a mental representation of Matt Bright. So just tell us a little bit about yourself for those who don’t know and remind me, but you know, what were you like? Where’d you grow up? What were you like as a kid?
Matt Bright:
So I grew up in Columbia, Maryland. I have two older brothers, but they’re eight and 10 years older than me. So I kind of, you know, was an only child from middle school and on, which was pretty sweet. I had basically my parents, they weren’t super overbearing, so I kinda got the ability to do what I wanted, which was fun. Definitely played sports.
So I played soccer, basketball and lacrosse in high school. Definitely dabbled in volleyball as well. I did not pick up golf until just probably about like three or four years ago. I had a good childhood, was active, an honor roll student. I switched high schools which is worth noting. So I switched high schools going from 10th grade into 11th grade. I went there to play basketball at a private school. Still played soccer and lacrosse, but no, it was not a huge shift. It was probably going from a school of like 1500 kids to a graduating class of 50.
Marc Gonyea:
So that’s a little unique. What was your favorite sport?
Matt Bright:
Probably basketball. So my middle brother, who is eight years older than me, he played basketball at Franklin Marshall. And so I was thinking about going that route, but decided to do a bigger school instead, and went to University of Maryland. Did the fraternity intramural thing instead, which I’m super happy about.
Marc Gonyea:
We’ll just back up a sec. So, in high school you’re playing three sports. That’s pretty good, man. And you were working hard in school. Do you have anything else?
Matt Bright:
I worked in the summer. I didn’t have any jobs throughout the school year, but I was always like a camp director. I was mostly just consumed with school and sports, which was super easy. I liked, you know, traditional stuff hanging out with friends and what not.
Marc Gonyea:
What did you think you wanted to be growing up?
Matt Bright:
Yeah, that’s a good question. With my parents, my father was a lawyer for the state and then my mother was a social worker for the state. So they were always pretty big into state jobs and having a pension and that whole career trajectory. My oldest brother is actually a teacher. My middle brother now is a lawyer, but he was a basketball coach at Colonel Gibbons for a few years while I was still at school. And so, I actually thought I wanted to do teaching and being a basketball coach.
And so, I actually had a double degree from the University of Maryland in history and secondary education. My fifth year at school I was entirely teaching and coaching over at Blair high school. Although I was also teaching at Northwestern high school. It was cool. But as soon, like literally the first, first month, first week when I was a teacher, like it’s a brutal, brutal job. Like the kids are going to school at, class starts at 7:00 in the morning. You have to get there at 6:30, it takes an hour to drive there. It’s hot as hell. It’s a dark classroom. You’re teaching history. The kids don’t care about it. It’s repetitive. So I knew immediately.
I was like, this is not for me, but I still stuck it out. And I really liked basketball coaching, but at the end of the day, I was like, do I want to do a job where my hobby is why I’m doing it? Or do I want to do a job? I can be a basketball coach and a sales guy. There’s no stopping that.
Marc Gonyea:
So this is the first thing you mentioned, sales guy, both your parents worked for the state attorney and a social worker. And that not really, there’s not a lot of direct connection with sales or was it, we were doing something in high school or like where it’s college, like when did sales kind of come up?
Matt Bright:
So, I was always pretty clever about things. I’ll give you some examples from back in high school. I transferred that year and that was a K through 12 private school. So there are a lot of people who had been there from, you know, from five years old on, and I was transferring in as going from 10th grade into 11th, summer after sophomore year. It’s a small private school. And so like some examples of me just being kind of crafty when I was younger. So they had this award and it was like the most prestigious award at the school. It was called the student’s choice award. It was the only award given to graduating seniors that was voted on by the entire class. And so traditionally that goes to somebody that’s been there since like age five and they know the entire community. I was the only one who was able to see through all that. And I was like, okay, if the students are voting on it, I’m going to campaign. And so I ended up winning this huge prestigious award, which really pissed people off. But that was kind of funny my senior year as well.
And this was the spring and I had already committed to University of Maryland. So I knew I was doing that. And lacrosse, it’s a fun sport, but it’s by far the most brutal during, during school, because like, it’s spring, you start it when it’s like February. And so it’s cold as hell or you’re on parking lots because there’s snow everywhere. And then by the end of it, it’s hot and you got all these pads on. It’s like, soccer’s all these, you started in the summer. You could see friends run all the time, it is brutal. So I didn’t want to do that. I wanted to play club volleyball at my old high school. So I was able to do that. And my parents weren’t too thrilled with that. I was like, alright, well, if I’m going to do this, I need some incentive. So, I ended up telling the coach, I was like, look, I’ll play lacrosse.
And the coach was a professional, a major league lacrosse guy. And so I knew he had access to resources. I was like, I’m gonna need a new stick. And I’ll also, and I’m sure it’s illegal, but I was like, I’m going to need a new stick. And I’m also gonna need to be the person who makes the playlist. And I just threw in music and I just threw in all these goofy songs. Like I did like basically the Caddyshack songs, like a song where it was Shaq, the basketball player, rapping. It was hilarious. It was all these songs that were funny to me. And then when we would play, and especially like on games where we won, it was all fine, but games we lost, they were always really pissed off they were like, we’re out here and we’re dancing to Shaq.
Marc Gonyea:
Did you get to play volleyball?
Matt Bright:
My conditions were met. So I still, I still did club volleyball or I did beach tournament, but yeah, I was always finding an angle to sweeten the pot for me, so to speak.
Marc Gonyea:
So kind of like sales, but not. That’s a clever incentive. I like it. So now we’re in college, right? You said there’s double major, but I’m going to be a teacher you’re thinking about I’m sure. I think we tried to listen to your interview back in the day. You may be considering going to law school.
Matt Bright:
No. So, so I wasn’t, yeah. My brother is a lawyer. My father was a lawyer. I didn’t want to, there’s a ton of reading and not that I’m against reading. I’m very active and I know you read a ton of stuff now, but like that just seems absolutely brutal. And just law school in general. But during the fraternity, I displayed a lot of things that I think correlated directly into sales. And so like, I was huge into recruitment.
Marc Gonyea:
When did you rush your fraternity?
Matt Bright:
So I rushed first semester, freshman year. That was also illegal. You’re supposed to have 12 credits, but I wanted to get in and I would like to add, and I’ll get to that in a second. But so I was really involved in recruitment and like, recruitment was awesome for me. Like I would be the guy who, when we had the recruitment, you know, after meetings and we would talk about the people, I would stand up there. I don’t know, I was probably a few beers deep and without a shirt on, I would just be up there rattling like 50, a hundred names. I’m like, Hey, here’s this kid, here are the people that he’s connected with. Here are the sports he played. He doesn’t seem that smart. Maybe he’s a tweener.
So, I ended up being recruitment chair. When I was recruitment chair, I would do some things that were really proactive. So like back then people would join Facebook groups. So it’d be like an incoming class or graduating class of 2012 University of Maryland. And so I would get through, and it’s a manual process, but I’ll just be like, okay, like this kid is good. It looks like a guy who’s going to join a fraternity. So then I message them and be like, Hey, when are you coming up for whatever it was called, like your summer session or whatever. And it’s a two day period. And I was living at school at the time. So when these kids would come up, I’d be like, Hey, we’ll pick you up. We’ll head on out. So like, I’ll take these kids out.
So, that when they came into school, I already had a list of 15 kids that I knew were going to join and they were going to join. So, I did a lot of that. I would during recruitment as well, every single house just had one party that they were going to, which is fine. But I was looking at that and I was like, man, this is just way overcrowded. And we can’t isolate the kids who we actually should get.
So I would have two houses throwing parties and I would go back and forth. And if I saw somebody who I liked, I would take them out of that house and put them in the good house. So we had one that was just like wrangling up all these kids. And then the other that was actually like being focused on recruitment.
So, I would do stuff like we had this whole thing where I was able to identify as well where poor money was getting spent. So we used to have like, the budget was something like $5,000. And, in my opinion, all of that should just be funneled into the stuff that’s actually driving people, not into just like stupid things. But one of the things was, we would spend like $3,200 every year of that $5,000 budget on this dinner at Olive Garden, which is like 20 minutes away. And it sucked and nobody liked it. And so I was like, guys, if we can just get catering from Bob Evans for maybe $500. And then I found a sorority who would allow us to use their house. And I was like, look, we’re going to get $500 worth of Bob Evans. We’re going to go to this sorority. We’re just going to have like, you know, make some rockets, have some fun, and then we’ll invite the sorority out afterwards to have an after party.
Chris Corcoran:
Alright, so you sound like you’re a bit of a, what I would call a recruiting aficionado.
Matt Bright:
Yeah. So I think one of the reason why I’m kind of positioning that as sales is like, one of the things that I think has probably been one of my biggest advantages is I look at this scenario kind of as a whole one. I’m like, okay, for that student’s award, for example, what’s the quickest way I could get there? Probably getting 15 kids that are actually influential kids to end up voting for me. And then they get some friends.
What’s the quickest way to actually get a recruitment class? Well, if I can get them in early, then they’ll start bringing the friends and then that’s the way of doing it. So that’s when I was doing that, a lot of people were saying, Hey, you should really start getting into sales. And then when I saw how I, how much I hated teaching, I was like, okay, this is actually a viable option. So the way that I started looking into sales was there is a job board on the University of Maryland site for job openings for outgoing graduates, I guess. And I took a look through that.
My whole thesis was essentially if I could attach myself to a company that would IPO, that’s the easiest way for me to make a ton of money. And so I was looking into tech companies, I found memoryBlue, and I was like, this is a really smart idea. The idea that you can get in on the ground floor of a lot of different companies and kind of gamble. So I liked the idea of poker chips kind of spreading your bets or maximizing your odds. So that was always my thing of being like, okay, if I could actually have not just one bet at one company, but if I could have kind of a vantage point into a ton of different companies and then pick my way from there, that seems like the most logical option. So I actually reached out to memoryBlue.
Marc Gonyea:
What did you see? What Chris may remember? What drove him to see us?
Chris Corcoran:
We posted it at College Park, it was posted on the job board or yeah, we’ll get there. But before we do, I just want to discuss that as a recruiting aficionado in College Park, it is a miscarriage of justice that you and Coach Williams didn’t compare metrics. So we used to post, we used to post at College Park and it was a target school. Still is just sleeping giant. And I know, you know, that I was not thrilled with how many, I thought that you were going to be able to bring us a ton of College Park kids.
I very vividly remember this. I went to College Park trying to crack into that school to a recruiting function, which was all centered around athletes and Greeks and lo and behold, I meet Omari Morgan and I start talking to him and he’s telling me he’s in a fraternity and I said, “Oh really? Which one?” He said Fiji. I was like, are you kidding me? Does the name, Matt Bright ring a bell? He’s like, yeah, of course. He’s my boy. So what, did you just want me to work for it? Because I knew you were a recruiting stud, but I wanted to see some of that in action for the health of the company.
Matt Bright:
So this was all set up.
Chris Corcoran:
Yeah. But we did get Omari Morgan. We did get Jim Gandolfo. And we got Dennis O’Neill. So what happened to that train and dried up?
Matt Bright:
Yeah. I guess Dennis, Dennis, let it dry up. So he, I actually suggested that he come here and he chose a different profession and then was looking to get into it after seeing kind of what I was doing. I thought it was a good legacy.
Marc Gonyea:
When you saw the ad at College Park, you thought it was an interesting concept. You wanted to kind of get exposure to a portfolio of high tech companies. So at that point you could evaluate and identify which one you thought would have the highest promise to IPO.
Matt Bright:
My whole thesis was if I can attach myself to a company that IPO is that’s how you make millionaires. And that thesis you what’d, you come up with it. Here’s actually the other thing too, this was back in 2011. So I had this idea of IPO in mind. And then I looked at like the Forbes, 50 most likely companies to IPO that year or something stupid, like 49 of the 50 were technology companies. And I was like, all right, I guess I better do this. And in addition to that as well. So I had the idea that I’d be good in sales. And I knew I wanted to make a lot of money.
And when I was thinking about software sales, that made a lot more sense to me than like medical sales and the reason being is because I look at medical and I looked at medical sales is kind of a profession of like, okay, if you were smart and you have a medicine background, but you didn’t want to go to med school, that’s probably the pool of candidates that get into that for software people. It’s not, it’s not people that were like really good at software. And they just said, you know what, I’m going to start selling it. It’s probably people that don’t have that much software experience. So it’s a lower pool of candidates that can make even more money. That seems like a no brainer to me.
Marc Gonyea:
Wow. That’s good. So you, so you joined the firm and kind of walk us through what happened from there.
Matt Bright:
Yeah. So I joined a new process real fast. So I remember, I remember Tiana reaching out to me. So Tiana reached out to me and the interview process seemed fine. I think we probably had maybe three interviews I interviewed with both of you if I recall correctly. And then Tiana and I was given the offer back in May or June, I want to say, but I had an obligation for a sale was for sorry, a summer camp directorship. So I finished that out through August and then I started that first week back. We’re building, this was the old courthouse road downstairs. Yeah. So I started there, I started the same day as Mike Breslin and Ashley Sparano. Shortly after Kurtis Michella joined shortly after Rob Saland. No, it was a really good crew. Clyde Kessler was already working at that time. I ended up living with Justin Brown and Kurtis at one point. So that was funny. Who else? Ian Robert. Brittany Bertolino. So, when I started Thaddeus was my delivery manager and they put me on an account that was it was virtual sharp, so it was an automated disaster recovery solution.
And so, I started with that and then there was also an account called CFN services that was basically selling like cable lines for high or like high frequency traders. So I did that for a little bit. And then those accounts dropped by honestly know no fault of my, but those accounts, those accounts ended up dropping. I got put on four to net, which I ended up working with for quite some time. And I actually loved that. I loved the people that I worked with on that. Kurtis’s on that account. I really liked them and I also had a Roambi as a client. And it was interesting cause Roambi was an account. So that was a mobile business intelligence solution. And they ended up getting acquired by IBM. And that was interesting, but I was working that and I was doing well. I think we had four people on the account.
So, if you remember, I was actually in the process of getting recruited out by them and they wanted me to move out to San Diego and I was like, all right, this is it. I’m moving out to San Diego, but it ended up falling through, which was really a blessing in disguise. Not because of the company by any means, but like I think thinking back on it, like my goal from the get go is to try to get hired out as quickly as possible. And I stayed here for two years. I did the whole memoryBlue sales, for the ladder there. That was super beneficial for me. Like if I would’ve gone there, my career trajectory would be so much different than it is now.
Chris Corcoran:
Do you think it was beneficial for you to stick out for two years here?
Matt Bright:
It was beneficial for me to be in the memoryBlue sales closing role for the second year. And in fact it’s, it was hugely beneficial. So like when I was in that role, so I, so I have those accounts and then coming on about nine months that I transitioned to supporting Tommy for the memoryBlue sales role. And I still had four net for about a three month span. And I was doing well from that and the idea was always the transition fully into a closing role, which ended up being true. So I did that for from August to August I guess what, 2013 to 2014. Awesome setup because one of the things that I think I’ve gotten really, really good at is being able to being able to, just to size up companies.
So, like in that role, you’re basically talking about VP of sales, CMOs, sometimes like directors, a lead gen, and you can just hear different from people and starting with them are just blatantly wrong. Like the idea that the inbound leads are what’s driving it or that you really don’t need sales reps in the role, or some of the SDR ratios are one SDR supporting 10 reps. Some of them are the other way, which is interesting, but like it just hearing how different VPs of sales view it, it puts a huge perspective on like, which ones actually value BDRs, which ones don’t, who set the reps up for success. Like some of these people had completely unrealistic expectations as I’m sure you guys see all the time, but being able to size, not only that, but then also being able to, I told you, I like gambling, but being able to handicap different companies, like I would talk to some of these companies, I’m like, what’s your target market? They’re like, well, you know, we’re really trying to sell into the Fortune 100 and I’m like, that’s awesome. So is everybody man. And like your product, it’s not like from what I’ve seen so far and kind of like where we’re talking, it’s a hugely competitive space. Do you have any clients? Well, you know, we’re working on that. I’m like start starting with a whale. Probably not the way to go, but, do it.
Marc Gonyea:
What advice would you have, would you have for yourself today, if you were, you know, the night before you started at memoryBlue, the advice for yourself, it’s also advice for, you know, all these people we have to start in the next 12 months.
Matt Bright:
My biggest advice would be for incoming memoryBlue people. It would be not to focus as much on the technology focus, way more on the sales, like CFN services and virtual sharp were the first two companies I started with. I was off of a month later, I spent that time. So focused on learning disaster, like mobile or automated disaster recovery and, you know, hedge fund cabling that would have been detrimental. You know, after the fact, like you do need to learn that as you continue going along, but like focus on focus on the sales fundamentals and be super open minded about stuff too.
Cause I I’ve had some experience talking with BDRs, both at my current company and my last company. And I’ve always been pretty hands on with them and you’ll talk to somebody who’s maybe six weeks in the job and they’re like, look, this is the approach that works. And I’m like, that’s cool, but you gotta build out your repertoire. Like you gotta continue building out your skills because if you’re literally only doing this one aspect of it, that’s not setting up for the long run.
Marc Gonyea:
We were smart enough to figure out that you just, you were really good at your job and we wanted you to stick around a little bit longer and you were Genesis, right? It was, Tommy was first and Matt was second. So you were the number, you’re the second sales person for the company. And you got some experience closing work. I know you talked about a little bit. Well, what was that like? Do you remember that?
Matt Bright:
I remember it. Well, I definitely like so I made a ton of calls and one of the things that you can dictate your paycheck here is that activity does get you paid. So I was always a really top person on dials. I was always a really top person on a talk time. And I think that was something that helped me. However, once you transition to that next phase, like not saying it all goes out the window, but it’s a totally new tool set. So I remember being sluggish off the back. I remember my first deal was a deal that I ended up sniping from Tommy. We split the territory or he got A through M and then I got N through Z. And N through Z was by far a worst territory.
So, and honestly, that’s probably advice I want to give to somebody starting out, but like for somebody who’s been here, and I still do just because I’m super competitive, but like caring about where you stand in the pack. It definitely matters, but I wouldn’t spend so much time and energy as I’ve done doing that, which has benefits because now I’m like, like I know, I know numbers. And I also like, I love call recording technologies. I’ll listen to the good reps. I’ll listen to the bad reps. I’ll listen to everybody. Cause I want to see, I want to see what’s sticking, but I want to see who’s got games and I want to steal, like I want to pick pieces from, I want to pick pieces from the other reps and learn. So like having an open mind is pretty important.
Chris Corcoran:
Craftsman. Yeah, it was good advice. . Let me make sure I understand. So you’re able to access actual sales calls or new sales calls and you go, it’s almost like an athlete looking at game film. You go and you listen to the top performing reps who you think are strong, whether they have the technique or the numbers to back it off, back them up. Most times those two go hand in hand and you go and you’re able to copycat their moves and then put your little map, right. Twist on it to make it your own. And then also the under-performance you looked on for things to avoid. Is that essentially it?
Matt Bright:
So yes, and at my last company we didn’t have any, any call technology. And so I advocated that we get gong and we ended up getting gong. And then I was by far the biggest user on it. Like if we actually tracked during our QBR is how many calls you listened to? And I was listening to a ton and they were like, yeah. So like, what are you doing where you’re listening to these calls? The truth is I’m looking to steal stuff. Yeah. That’s my practice. And I want to know, I want to know kind of the nuances. I want to know when you’re talking about competitors. I want to know how you’re talking about competitors. I want to know how you frame the pricing. I want to know how you’re explaining the value proposition. And I want the value proposition to be super crisp. Like if you can’t teach your prospect how to sell after the fact you’re doing yourself, a huge disservice.
Chris Corcoran:
I want to say something here because it’s important for the listeners. So companies, they go out and they, you know, they have the product, they have the sales, they have the compensation plan. They have all those things in place. They invest in the technology of the call recording all of that. And you, and all your contemporaries at the company had access to those call recordings. But was you and you were doing this because you wanted to do it. Not because your manager made you do it. It was all because of you that you took it to the next level. And so it’s kind of really up to you or the individual in terms of how high you want to go and ask successful. You want to be that burning desire to succeed, which I know you have.
Matt Bright:
Yeah. And it’s like, call recordings are a really good example for them or for it because especially people who have been in sales for 25 years they’re not familiar with this. And a lot of people have a pushback pretty immediately. Cause you’re thinking, Hey, this is just big brother, to an extent of this. And what I would say is like, look, if, if you’re not performing, then that’s probably something the company should know. And for the reps that are like looking to get started, especially like whenever I start a new job and I did this out, I’ve done this at every single company.
I basically take one call recording. I’ll listen to who I think is probably one of the better reps or best rep that I can find. And then I’ll just transcribe that entire call and just steal it verbatim. And then from there, I’ll actually go back through and start changing it because I’ll see things that resonate things that don’t resonate things. I think I can shorten up, but like when you start a new job, like I don’t look, I don’t know the technology. Like I like to think I’m technology competent, but I’m not as competent as somebody who’s been in the role for 18 months and had deals. So I’m going to steal absolutely everything from them and then put my own spin on it.
Chris Corcoran:
I have to ask where, where was this zest for call reviews when you were at an SDR for memoryBlue?
Matt Bright:
Yeah. That’s a good question. That’s a good question. I think it was always there. I think it was a burning desire that just got more as I age
Chris Corcoran:
What were we doing? Good call. Bad call. When you were, when you were an SDR?
Matt Bright:
Yeah. So we did this, we had to do a good call, bad call. The, the thing about there is like a BDR calls. It could be three minutes long. You get somebody on it, piques their initial insurance. There’s not a ton of nuance with it. There’s a lot of skill, but in my job. So I do enterprise sales.
Chris Corcoran:
Can you explain to our listeners what that means?
Matt Bright:
Yeah. So, so I’m an enterprise sales and I’ve been lucky enough to be in that role since I guess 2014. So pretty immediately once I switched from a memory blue, I was in enterprise sales and that’s probably the highest degree. I mean, it’s the highest degree of outside selling with the acceptance of, or the exception of directors, managers, but like I’m selling into the largest companies and trying to sell the biggest deal. So it’s not transactional. It’s a very strategic sale. There’s a lot of different buyers involved. Like I could think about deals where I would have to group in, I mean sometimes like 30 plus people from different organizations. And the idea is if one of them and usually don’t have a ton of visibility into this. So, you need to find some back-channel ways to get information.
I mean, if you have one person who’s, you know, speaking negatively after the fact, or if you don’t train your champions to sell internally on your behalf and you’re not there, that’s how you win or lose deals. I love to say I’m as influential as possible, but the truth is like the most influential person at the company I’m trying to sell to is way more influential than me and calls or deals. Even though there are nine months long are typically one on it’s like a five minute conversation. Like I’ve done deals a fortune 100 insurance company. And it was an in person meeting. It was, it was actually just a few people there. UI had a technical resource. I had my boss and then they had two people on their side. One was more business focused. One was more technical focus.
We get through the demonstration and we had an hour-long meeting. The last five minutes that meeting my technical guy was talking with their technical guy and the business guy was like, yeah, so this looks good. I’m like, great. So like how do we actually get this deal done? Like if there’s interest in moving forward, we’d love to do what we can to put ourselves in a good position here, like help us. We we’d love to help you. And like that, that five minute conversation is what closed a deal that probably took like nine months maybe to close. And that deal was upwards of it. It was just under a million, but close to it.
Chris Corcoran:
Since we’re in the process of talking about deals, finish that story about that deal you sneaked from Tommy.
Matt Bright:
Yeah. So I had N through Z and I had just started and it was, yeah, it’s a great territory. Zscaler is literally the only company I can think of. I transitioned to the role. You all had a hard transfer rule, I think. And so tell me what was on the doorsteps. Exactly. Which is a great account. And I ended up taking that and I was like, this is well done, Tommy. So the thing that’s so cool about this place too, is like you get it, it’s transactional. You prove out value quickly. There’s not a demo like the fact that it services like you either buy into the story or not. And I think that selling this, like this is a really, really skillful sale because you can’t rely on the product. I think a lot of, and I’ve been fortunate enough to work for some really, really good technology companies. And sometimes it’s easier because the product shines and that’s awesome. And you should try to find that to treat as little friction as possible, but like selling memoryBlue and having to sell the story and the ethos and the why behind it, like that’s really skillful. And I succeeded over Tommy.
Marc Gonyea:
Okay. You hit on it earlier, but I want to bring it back out. Cause I think for people early in their careers, you brought it up, but maybe you spent a little too much time earlier worrying about how other people were doing compared to you. Can you go into that a little bit more?
Matt Bright:
So, and I still talk to SDRs to this day about that where somebody else’s success takes away from yours or somebody’s got something easier or there’s an inbound lead and like the truth is that’s always going to happen, but what I focused on a lot more now and like, I’m still just as competitive as I was then. I don’t see it as kind of a zero sum game. Like there’s definitely ways to build out your network and like some of the things that I’ve gotten a ton better with over, especially the last, like, I don’t know, three years or so is not being as not being as kind of single threaded in the bigger picture. And what I mean by that. So like when you’re talking about deals, if you only have one point of contact, that’s single threaded. If you have 15 points of contact, that’s multi-threaded. So when I’m selling it to a company, now it’s awesome. If I’m in, hopefully I’m not telling it to a single threaded opportunity, but if I’m selling it to those 15 people as a company, that’s all really good. And that’s good that I’m doing that. I’m going to continue building that out.
But now I also want to know, like, who else has sold to this company? So like, when they’re talking about integration points, I’ll start reaching out to those reps. And I’m like, Hey, I’m talking with this group. Is this the group that sold that deal for you? And they’ll be like, yes. Or there’ll be like, no, and then I can course correct. I’ll ask about partners. So, and partners for the listeners, it’s a mechanism of selling through somebody. So, a lot of larger companies only like having one person that they’re doing financing with essentially. And so instead of my company selling directly to them, I’ll sell it to another company who then take the, the ownership over the financing and the billing. But I want to know whether that partner has influenced. I want to know. I just want to know more, I want to know more about kind of what’s gonna win this deal or what could potentially lose it.
Marc Gonyea:
Why is that so important? Knowing more?
Matt Bright:
I mean, for forecasting is one aspect of it, but more so than that just gives me the biggest probability of win. Like I, no matter how much you try, you’re not going to close a hundred percent of the deals. But as long as I give myself enough outs and I have enough information to then justify why I’m forecasting or why I think this is going to be there, it’s like you can sway deals that were probably on the fence. So that’s, that’s the reason.
Chris Corcoran:
Yeah. Insanely curious, what’s your most memorable deal, win or lose.
Matt Bright:
So my favorite deals are, and they haven’t been the biggest I’ve sold, I’ve sold a $2 million plus deals. And one of ’em was an awesome one. It was a huge financial organization. I got really deep within the account. I still am on a texting relationship with some of the people I sold with, even though that’s not my current company. And there’s no, there’s no added sales benefit. I just, I liked the people and they helped me out and it was a good relationship, but my favorite deals are the ones that I self-source, because I know that that’s my biggest value add, an inbound lead that closes for a hundred thousand 500,000. I’ll take it, trust me. And I’ll like that, but it’s, it’s more impressive in my opinion, to get an outbound deal where you’re, maybe you’re just getting an initial foothold in the account, but without you being there, that deal one of clothes. And I’ve done that to, you know, one of the largest tech companies that all our phones on are in California, one still the largest retailer in the North. I’ve done it a big, big,, big companies, and those deals wouldn’t have happened without the outbound outreach.
Chris Corcoran:
Wow. So you kind of, I guess, satisfaction, is that what it is that you get?
Matt Bright:
I just think it proves my value more like that deal would not have come in without me. And you could argue, Oh, you know, like there’s been marketing stock, they’ve been poking around our website. That deal wouldn’t have happened just wouldn’t have. I mean, for enterprise sales is it’s, it’s funny. Candidly, it makes me a lot more marketable like being able to do it from outbound perspective. It just makes me a lot more marketable it’s to know that I can go out there and hunt for enterprise sales, getting back to your question on like how often it happens now, thinking back historically, if I could close10 logos a year, that’s a, I’d say a huge year for me. And the outbound sales process, especially some of these enterprise accounts. I mean, it’s not unheard of for it to be a 15 month process.
So, the only way that I can feel comfortable in my current role is if I’m building up enough of a pipeline. And one of the things I love love, love about advocating for BDRs and like initial meetings is like, when’s the last time you’ve actually had an initial meeting who is with the person that signed the check. Like very seldom. It’s always with a guy who’s just curious, or a guy who maybe owns the problem, but he doesn’t sign the check. And so like, you need to get that initial foothold in there. And then you expand out from it. Like if you’re selling into a more transactional sale where you have 20 deals a quarter and you do have a good flow of inbound versus outbound, that’s different. But like for outbound, I need to have, I need to have a ton of initial meetings so that I can start poking holes in some of these bigger accounts.
Marc Gonyea:
How did you make the move from an inside guy, closing promotional services deals largely over the phone to, okay, I need to get into it. I want to get into an enterprise sales role. How did you make that happen? And what advice would you have for folks who are trying to do that?
Matt Bright:
So I had kind of a funny, a funny situation with it. So I was selling memoryBlue and I did kind of a package deal that got, got me to that company. So they were both looking for BDR services and they were looking for an inside sales rep. The inside sales rep compared to BDR can vary dramatically at a lot of different companies. Sometimes an inside sales rep is a BDR. Sometimes an inside sales rep is carrying a number sometimes in sales, inside sales rep is actually closing enterprise deals. So like understanding what that is, and kind of drilling down for interviews is important, but at that company, so I sold BDR and I also sold myself as a outsource placement for an inside sales roll.
Marc Gonyea:
Yeah. We got paid on you leaving.
Matt Bright:
So I go to this company I liked the VP of sales. He was very, very mellow kind of let you do your thing. I joined, there was one other inside sales rep with me. She had been there for, it was her first job right out of college. And I’m actually like best friends with her today, but it was her first job out of college. I had just gotten placed there. I liked the VP. I was supporting this rep. And two weeks after I joined the VP of sales gets fired and I’m like, Ooh, this isn’t good. So, so now, now I have that going on. And then about two weeks after that, the rep that I’m supporting gets fired and I’m like, this is not good. The CEO ends up getting fired about two weeks after that at times it was startup.
And so, I remember like going back to, I was living in Northeast DC at the time with a few buddies and I would come back and full like no joking about once a week. I’m like, yup. This guy just got fired. This guy just got fired. And so they had this investor he was actually super influential for me. His name was Andy Miller. And he was an investor. And then when the CEO ended up getting, let go, he ended up taking over as the CEO and he reached out to me and he reached out to the other inside rep, but separately, and he goes, Hey, we’re going to really build out this inside sales channel and also actually really correctly. So when I first joined, like my first day there, I kinda like got the lay of the land. And then I just started hitting the phones and there was like a super quiet office and I would do the memoryBlue spiel. But you know, obviously for my technology company now, so like immediately people were looking at me and they were like, this guy is a really, really good BDR. And like the CMO called me in and was like, I’ve never heard anything like this. Like you’re doing all this really good work and you’re talking on the phone and like, I can’t believe what’s going on. And so, like I was doing really well in the role.
And so, when they were letting all these people go, that new CEO is like, Hey, I know there’s a lot of changes going on. We’re going to build this inside sales model around you. And Julie was the other rep regarding build this sales model around you guys stay with us. Like, it’s going to be fine. We’re really going to build this out. So I came back to him and I was like, look, I appreciate what you’re saying. Let me offer you something else though, put me in that outsize role or in that outside role. And I guarantee you I’ll be the top rep this next year, put me in that outside role. And he was like, okay. So he thought about it. And then two days later he came back and I was like, all right. So we’re going to give you a patch and we’re going to give Julia patch. And they bumped up our salaries. And I remember distinctly, like in that meeting, that he was telling us that me and her left immediately after, and the kind of caught wind the steel stairwell. And we were like, Holy s*** this actually just happened.
I’m 24 at the time, I’m going to enterprise sales role where, I mean, my counterparts at any other company are the, and especially at this time, like they weren’t giving this to like 25-year olds. So it was like 40 year olds. Plus I make it sound, I make it sound like a bad thing, but now like it’s much older seasoned people. And I was like, this is awesome. So we’re in this role, I’m generating pipe a month after that CEO’s out. And I was like, this is not a good sign. So I started poking my head around then and a new VP of sales came in and he was like, Hey, like I’m taking a look around, we’re going to hire some more seasoned vets. And I was like, okay, look like I understand I’m 24 years old. You’re looking for people that are 40 with the exception of that 20 year of background. Like, is there anything I can do to keep this role? And he was like, no, no, you can’t. I was like, alright, well understood.
So, I start poking around and I started leveraging my enterprise sales role that I’ve been in for like the last year. And I, and I’ve done this at every single company. So at threat track, I sold myself or at my first place I sold myself out to threat track was my first company. That’s where I sold myself out to a recorded future is where I went to the next. And then I’m at Snyk now. And at each of those places, I’ve always reached out to the VP of sales and that’s how I’ve gotten the job. Every single time I reached out. I saw that recorded future. And at that time too, I had the I had kind of the knowledge coming fairly recently from memoryBlue. I knew I wanted to put myself in a cyber security or a big data field. Like at that time, big data was super, super hot. I saw cyber security selling really big deals and recorded future was like the perfect mix of cybersecurity and big data. And I was like, this couldn’t be any better. And so I reached out leverage my current enterprise sales role.
And what was kind of funny about that was when I reached out. So Jason Heinz is the VP of sales at recorded future. At the time I reached out to him and I was like, Hey, interested in this role, they had an open position for the Southeast. And he was like, okay, like, let’s have a meeting. So during the interview, he was like, look, we just gave that Southeast position away. But I kind of like what you’re bringing to the table. What if we gave you an international role? And I was like, tell me more. And he was like, look, I can give you all of Asia, all of Australia, all over of Africa, South America. Like, I can give you even UK for a little bit, like we’re hiring somebody, but I can give that to you for like the next few months. And I was like, okay, I don’t know, man, like, then that seems like a really tough, it seems like a really tough jump. And so I thought about it and I came back and I was like, look, I can’t sleep at night. If I’m going to be an international sales rep, that just seems like a ludicrous move. What I could do though, is carve out another patch, carve out like a mid-Atlantic patch for me. And I can take that job knowing that I’ve made a right decision. So, he carved out Maryland and DC.
What was funny about that is I ended up closing the biggest bank in Australia. I ended up, I ended up closing a few deals in the UK, but two months after, like, the thing I love, love about startups is there’s just so much chaos that you can just move freely throughout the organization. So I started in that role, I was there for two months, people get promoted. I ended up taking the Midwest patch, closing some of those big deals I talked about earlier was there for six months. Then the West coast patch opens up and I’m like, yeah, like California, it’s selling a tech solution, sign me up. So I joined that and then New York was struggling a bit. So they were like, Hey, do you want New York? And I was like, yes, yes. I want New York. Yeah. So like, I I’ve always been similar to like me changing high schools, you know, being kind of methodical with like how I found sales. I’ve always looked at it very pragmatically, I think on choosing new opportunities, finding new roles. And I do a ton of research on like, look, if I’m about to take this and I’m kind of shifting gears now, I was talking about the patches before, but for like startups, I won’t go to a startup unless if they have like a legit backer behind them, like for me, that’s incredibly important.
Chris Corcoran:
What do you mean?
Matt Bright:
Like a VC. So I, so traditionally I was kind of following the market or the industry I should say. So like, I really liked big data. I really like cybersecurity. And then as I started looking into it more, my new thesis is that good VCs are gonna produce positive outcomes for their portfolio companies. So if I can actually attach myself and get like a good run with what I consider to be a top VC, that’s just a way better bet than me going with somebody. Who’s maybe a new founder and bootstrapped, and they’re looking for their initial, you know, sales person, like that’s super unattractive to me, but finding, finding a company that has good backing has portfolio of companies who’ve had successful exits that’s super sexy.
Chris Corcoran:
I agree with everything you just said in terms of the pedigree of the VCs and the niche and all those things are super important. The challenge I have is sometimes I talked to Matt Bright when he was an SDR when he was here for six months and wanting to get the first flight out of the, off the Island, right. To go work at a company that you described is super unattractive to you. Like how do you reconcile that? Or what would you, what advice would you give to an SDR who’s looking to their first role, post memoryBlue, what would you recommend?
Matt Bright:
Find a good pond. Like if you, if you’re getting lowered by a slightly higher base, and you’re one of the first reps that seems like a recipe for disaster, but like, if you can find yourself in a place where they’ll actually give you a closing role and a place where you could actually see the path to the outside, and I’ve heard other people talk about it too. I think it’s incredibly important. Get yourself like my suggestion would be get yourself outside and as in as high of a role as possible, because it just gives you out, like in an enterprise sales role, if I ever did want to go and do more transactional, I at least have the enterprise background where I could then do that.
If you’re trying to jump from a SMB role to an enterprise role, that’s going to be super tough. So find yourself in kind of as find yourself in a path to the outside and as high of a role as possible would be my suggestion. And like a lot of people will talk about like the magic number is always like, look, if you’re here for a year, you can make a hundred thousand dollars first off, that’s probably wrong. And second off you can make a lot more money doing different things. So like, just get to the outside.
Chris Corcoran:
Get to the outside as quickly as you can, would be your advice though?
Matt Bright:
This is probably not what you’re looking for with that.
Chris Corcoran:
But, and then how do you do that? Like, what do you look toward it?
Matt Bright:
I said earlier I like chaos, I really like it, especially early on. Like while that first company I worked for I actually do not know how they’re doing by, there was a ton of people getting fired and it was just a pretty chaotic situation that was super beneficial for me. So like, I wouldn’t look at everything and kind of a negative line being like, Oh man, like my rep just got fired. Your rep gets fired, ask for his job, find a way to take advantage of a, of a bad situation. And then like, if that looks like it’s going sideways, leverage it, leverage it to the extreme.
Marc Gonyea:
Yeah, dude. That’s how I got my first sales job. So this is what happens you have to, because they’re looking for people to step up and if you’ve got some game and you’ve shown some, you got a work ethic and you’re interested, you’re a great choice.
Matt Bright:
And so one of the things too is I think it’s pretty binary on people that want somebody with 25 years of experience or somebody that’s willing to take a chance on a flyer for the people that are looking to leave, go with somebody. That’s going to take a chance on a flyer. Like if they’re sitting there and you’re looking at all the other reps and they’re like 50 and, and again, like not ageist by any means, it’s just kind of the profile of people. Like if there’s somebody that has 25 years of sales experience, and sometimes it’s even more niche. Like if they’re like 25 years of networking sales experience, you’re not going to the outside. Like you’re just knocking into the outside in the next two years and you can go there if that’s fine.
But if you’re looking to get to the outside, like the other inside sales rep that was promoted with me from the first company, she’s a top producing rep now, like younger people can add a huge, huge benefit to companies, but we both found, so she actually ended up leaving that first company and joining me at recorded future Jason, who is the VP of sales at the time was open to take a flyer. And it was really, really beneficial for both of us. Like we produced crazy numbers and we were proud. We weren’t as well paid as somebody who had 25 years of sales experience. They’re like, it’s a home run for him and a home run for us. Right.
Marc Gonyea:
So we’ve talked a lot about the company. Let’s talk a little bit about the person you work for. How important is that? The way I phrased the question is what’s more important, like a good company and it not good boss or a, not that a company and a really good boss. What do you look for?
Matt Bright:
That’s a good question. And I kind of go back and forth on it. Like sometimes, sometimes I think to myself, like, look, I can handle one or the other, but while this isn’t necessarily answering the question, there’s so many companies out there find both like, it’s stupid to settle for one or the other. Like if you’re with a really good boss and I see this happen all the time, or like a colleague of mine ends up getting a VP of sales role and then a person will go and join them at like just said, in my opinion, like a really risky company, I don’t know if that’s beneficial, like find yourself a really good company and a good boss. Like you, you don’t need to like research be as greedy as possible, be as greedy as possible. It’s only going to be beneficial for you.
Chris Corcoran:
Ready to invest your most precious asset, which is your time, right?
Matt Bright:
Yeah. A hundred percent agree.
Chris Corcoran:
How do you keep your skills sharp?
Matt Bright:
I continue to read all the time. And I listened to a ton of podcasts. Like I listened to like the John Barrows and I’m reading a lot of books. Something has changed for me a bit is I do less specific sales stuff, everything I read and choose to read. I’m kind of putting a sales angle on it. So like, I’m reading man. Like I read book about like game theory and like, I think that’s super important stuff. No, but like, I read a lot of books about like I a brutal read about how people end up getting into depression. But the reason why I read it was because it does a really, really in depth job talking through like how the brain works and like, you know, what motivates people. So stuff like that, I find a lot more interesting now than like somebody being like, when they ask X answer, why? Because that’s super, I don’t know. It’s, it’s an art. And so I’d be more interested to see how people think and how people react to things than so specific to like, when you’re talking to the CSO, you should be answering this way. Like, that’s less interesting to me.
Marc Gonyea:
These are a lot of practice with the question stuff. I mean, you put a lot of work into your game. It’s only natural work on other parts of your game to improve and develop and carry out how the human mind works or why people say certain things, certain ways or game theory, that’s all different parts of the game. What what’s the biggest mistake that you’ve seen your memoryBlue contemporaries make post memoryBlue?
Matt Bright:
Probably something we alluded to earlier and just looking to get the first ticket out or not thinking strategically about kind of how their next role aligns to their follow-up role. Like if you, I mean, it’s kind of scary, like it getting to the field. And I think you guys used to talk about this as like the velvet rope. Like once you get there, you’re kind of in, and it’s like, especially like on the enterprise sales side, like it’s, it’s a really tough spot because there’s always going to be somebody saying like, Oh, well, can they close? Oh, well, can they close bigger deals? Can they close more strategic deals? So if you don’t choose a good spot, then you can find yourself in kind of a downward spiral where now you’ve had five years of inside sales experience and someone goes well, in addition to me having fear on you in a closing role, how come nobody else has given you that? So like, that’s a really scary spot to be. So find somebody that believes in you and is willing to take a flyer like, and that don’t take that advice. I think definitely it pays negative dividends.
Marc Gonyea:
Thanks a lot, man.
Matt Bright:
Really appreciate it.
Chris Corcoran:
A lot of fun.
Matt Bright:
It’s been fun.
Chris Corcoran:
Thanks a lot.