Matt Roberts got into tech sales almost by accident. He was pouring wine in Santa Barbara when friends pulled him into an SDR seat, and he rode that start all the way to director of sales development at Chili Piper. These days he places reps at AI-native startups. Ask him what he screens for and the answer is coachability and curiosity, ahead of experience every time. In his view no good SDR is missing either one, with grit and a real team-first streak close behind. He’s blunt that booking a meeting is harder now than it was in 2019, and that your online presence often decides whether a prospect even bothers to reply. The two things most early-career reps skip, building a network on purpose and making yourself hard to replace, are the ones that pay off for years.
[00:00:00] Matt Roberts: ...working with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:00:08] Matt Roberts: I think, you know, booking a meeting in 2019 was a lot easier than it is in 2026.
[00:00:14] Matt Roberts: And so if you're somebody who's going to give up at the, not even the first no, if you're going to give up at the 50th no or the 100th no, like this isn't the job for you.
[00:00:21] Matt Roberts: We also had little like weekly, and then it turned to monthly, like awards. One of them was called Animal of the Month, one of them was called Unicorn of the Month. Animal of the Month was like someone who went above and beyond. Usually it's obviously like quota-based, but if there are two or three people blowing out quota, like still it's going to be a group voted and selected champion. And then the Unicorn was the person who was the most helpful. So maybe it's somebody who helps with like a call script, or a sequence, or a template, or a new workflow with some of the tools.
[00:00:52] Matt Roberts: I remember trying to help like lawyers like share their screen in 2014, and it was like a pain in the ass. Like you could spend 15 minutes sometimes just trying to get them to share their screen, and like it was nuts.
[00:01:03] Matt Roberts: And to your point, like if someone hits me up, I go to their website and it looks like it was made in 2005, I'm like, "All right, I'm moving on." Like it sounds crazy, but yeah, like that stuff is so valuable.
[00:01:14] Matt Roberts: And I promise if you hit up 10 of them and say like, "What's up, John? Saw you work here. Would love to learn how either you broke in or just like how it's been. Like would you be down to chat for 15 minutes?" If you send out 10 of those, you're going to get like three or four that respond. And all of them were in that same seat as you at one point.
[00:01:29] Matt Roberts: And then now when it comes to, you know, five years down the line, yeah, maybe you never worked for this person because they weren't your BDR leader, but you knew this person in product or marketing because of whatever reason. Now they're at this really sweet company that you like, and they're going to vouch for you because they're like, "Yeah, I worked with John five years ago. Yeah, John was a BDR, but like he always, you know, was interested in what we were doing in product, and so we talked about stuff and I shared things with him, and like he's really bright. Like I would give this guy a shot."
[00:01:57] John Karsant: Welcome back to Prospecting Pros, and on today's show we have Matt Roberts. Welcome.
[00:02:04] Matt Roberts: Thanks for having me, John. Excited to be here.
[00:02:06] John Karsant: Yeah, so I've actually been, I've seen Matt, we've been connected for a while. We've never really spoken, but I've seen Matt's posts for multiple years, I think going back to when you were at Chili Piper. And when I was looking for guests that have a expertise in SDRs, I was looking at your profile and I thought you'd be a great fit to come on and talk shop.
[00:02:28] John Karsant: So, why don't you tell the audience a little bit about, you know, your, some of your previous jobs you've held and where you are today.
[00:02:36] Matt Roberts: Cool. Appreciate the time and the intro, John. Glad to see somebody's seeing the posts as well. It's been a long, a long run. So, yeah, as far as my background goes, I always tell people I sort of fell into the tech sales dev world by accident. The reason I say that is I went to school at UC Santa Barbara. A lot of my friends were doing something called the Technology Management Program at the time, which was a lot of people ended up going into sales, product, etc., into the tech space. This was around 2013.
[00:03:08] Matt Roberts: Whereas I went to LA to work on music videos and reality TV. And lasted there about a year and a half, a little under two years. Moved back to Santa Barbara because all my buddies were there, and was pouring wine and just, you know, getting by, bartending. And they would come in on the weekends, and I would be serving my friends, and they had their, you know, fancy SDR money at the time.
[00:03:33] Matt Roberts: And they kept saying, "Hey, you got to come join us. Work with us at a startup called AppFolio." There was a few different startups in Santa Barbara that were getting a little bit bigger, Procore being another one. And I just took an interview, and next thing you know, I was working there and had some of the best times of my life. Early stage, you know, SDR role, working with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:03:58] Matt Roberts: About a year and a half into that role, after I'd been promoted to an AE, I got pretty burnt out and was like, "I don't know if this is for me, and I don't know if I want to do this forever." So I quit and I traveled. I was just telling you a second ago, my sister's out in England. I did a big Euro trip for about four months with a good buddy, and came back, went to my hometown up in Northern California, where is as far as you can get from the tech world, and was just figuring out what was next.
[00:04:26] Matt Roberts: After a few, like a year and a half, two years of a passion project with a buddy there, I said, "Hey, I need, I need some paychecks again." So decided to get back into the tech space because that's what I knew.
[00:04:37] Matt Roberts: And that's when I sort of like really kick-started my career, which was I was looking for a remote role. I had the AE experience, but I was like, "I don't know if I want to be an AE again." And so I was just like, "I want to find the right company. I'll come in as an SDR, and I'll, you know, kick butt there and see where it takes me."
[00:04:53] Matt Roberts: And so I found an 18-person company that was completely remote pre-COVID called Chili Piper, and said, "Hey, this looks kind of interesting. Maybe I'll apply here and see what happens." And then long story short, got hired as SDR number three there.
[00:05:00] Matt Roberts: ...got hired as SDR number three there, and within about six months, I was the SDR manager. I started hiring people, and about a year and a half later, I was the director of sales development, and I had managers and a team of 20-something under me.
[00:05:18] Matt Roberts: And so that's what I always say kind of really kick-started my career, but I completely fell into it, and it wasn't my choice. It just kind of felt like it was part of the journey. And since then, from Chili Piper, I moved into the head of sales development role at Mosaic, which was an FP&A platform for a little under four years.
[00:05:35] Matt Roberts: And then about a little over a year ago, we were acquired by HiBob, where I moved into a role that was very strategic, less building and growing and leading a sales team, which I quickly realized that's what I love the most about that sales dev leadership role.
[00:05:50] Matt Roberts: And so then I got connected through a few different buddies who are building go-to-market teams at a company called Vibe Scaling, and now it's called Crew, where all we do is place talent at AI natives in San Francisco and New York City. And so I joined them about two months ago now, so...
[00:06:07] Matt Roberts: ...all a long way to say, fell into the tech world, was an SDR, was an AE, moved into sales dev leadership, and now I place SDRs, BDRs, and sales dev leaders at some of the fastest-growing AI natives in New York and San Francisco.
[00:06:19] John Karsant: It's a cool story. I love hearing how people got into like the sales or tech world because it's typically never a straightforward path. There's always like, you know, what you're doing, you're traveling. For me, I was just on a podcast right before this and I was talking about how I was a tennis coach, quit my job, moved to Argentina, needed a remote job, and you're just looking for almost anything because this was before COVID.
[00:06:42] John Karsant: Chili Piper was actually one of the companies on my list that I was eyeing because it was one of the few that were out there and like, they were remote first, and at that time, that was really important. It was more important to me than the money at that time. But yeah, I love hearing those stories.
[00:06:58] John Karsant: What really stood out to me as I was looking over your different jobs you've had is how many people you've hired, which really makes sense of how you got to where you are today, and now you're actually focusing on that 100%. Let's talk about that because, for me, we're constantly hiring SDRs. I don't do the hiring myself, but the team, and like, it's challenging.
[00:07:20] John Karsant: You've probably seen just about everything from the good, the bad, the in-betweens. Walk us through like what do you look for when you when you do hire an SDR? What do you look for actually in an interview, and then also post-interview? Because people can interview well, right? And they make it past that, and then you kind of bring them on, you're like, "Oh, a little bit different than I was expecting." What do you look for also post-interview to make sure they're a good fit?
[00:07:47] Matt Roberts: Yeah, good question. And funny enough, like you said, this became my my superpower and also what I love the most. And so I made a post about when I joined Crew as like, "This is my ikigai," which is like, I think I'm good at it, I love it, it can pay the bills, and like it makes the world, you know, quote-unquote, a better place, it's not harming anything.
[00:08:10] Matt Roberts: And so this has been very, very passion, passionate hobby, whatever you want to call, outside of just work, and I would always place people elsewhere whenever I had the chance because sometimes, to your point, we interview a bunch of people, I'd have one role open or two roles open, but there'd be like four or five people that I'm like, "This person deserves a shot," and so I'd then like go out and and help place them.
[00:08:31] Matt Roberts: But as far as like what you're looking for, and it's changed a lot, I'll say that too, with AI, with everything that's, you know, how fast the role has advanced and how different it has become. What I was looking for at Chili Piper in 2019 is not the same as what I was hiring for at Mosaic in 2025.
[00:08:49] John Karsant: Makes sense.
[00:08:51] Matt Roberts: But like some of the things I think just like table stakes are... We actually had a podcast episode with Andrew Frouning over at Saasira the other day, and he had a framework that I really liked, which I can say maybe is similar to the way I would approach it anyways. He calls it CHAMPIONS framework, which is like coachable, humble, adaptive, motivated, play as a team, intelligent, open-minded, nimble, and savvy.
[00:09:16] Matt Roberts: And so like just looking at that as a as a framework and sort of the way that I have always thought about hiring, there's some that I'll I'll take out of there and say are the most important. And like the first two, which actually could be C and C, either way you want to put it, coachable and like curious are two big ones that like I don't think there's any SDR, BDR out there that's really good at what they do and are not coachable or curious.
[00:09:39] Matt Roberts: As you know, it's like the growth mindset, right? You're you're looking for people earlier in their sales career, and just like you mentioned tennis, you know, like if you're somebody who doesn't want to get better every single day, like you're not you're going to be a terrible sales rep in general, and you're never going to work as an SDR or BDR.
[00:09:55] Matt Roberts: And so like that one is a huge part, and, you know, you got to make sure you can suss that out through role plays or just anything in the interview process.
[00:10:00] Matt Roberts: ...work with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:10:08] Matt Roberts: I think, you know, booking a meeting in 2019 was a lot easier than it is in 2026. Um, and so if you're somebody who's going to give up at the, not even the first no, if you're going to give up at the 50th no or the 100th no, like, this isn't the job for you.
[00:10:21] Matt Roberts: We also had little like weekly, and then that turned to monthly, um, like awards. One of them was called Animal of the Month, one of them was called, uh, Unicorn of the Month. Animal of the Month was like someone who went above and beyond. Usually it's obviously like quota-based, but, um, if there are two or three people blowing out quota, like, still it's going to be a group, uh, voted, um, and selected champion.
[00:10:44] Matt Roberts: And then the Unicorn was the person who was the most helpful. So maybe it's somebody who helps with like a call script or a sequence or a template or a new workflow, uh, with some of the tools.
[00:10:52] Matt Roberts: I remember trying to help like lawyers like share their screen in 2014, and it was like a pain in the ass. Like, you could spend 15 minutes sometimes just trying to get them to share their screen, and like, it was nuts.
[00:11:03] Matt Roberts: And to your point, like, if someone hits me up, I go to their website and it looks like it was made in, in 2005, I'm like, "All right, I'm moving on." Like, (laughs) sounds crazy, but, um, yeah, like, that stuff is so valuable.
[00:11:14] Matt Roberts: And, and I promise if you hit up 10 of them and just say like, "What's up, John? Saw you work here. Would love to learn how either you broke in or just like how it's been. Like, would you be down to chat for 15 minutes?"
[00:11:23] Matt Roberts: If you send out 10 of those, you're going to get like three or four that respond. And, and all of them were in that same seat as you at one point.
[00:11:29] Matt Roberts: And then now when it comes to, you know, five years down the line, yeah, maybe you never worked for this person because they weren't your BDR leader, but you knew this person in product or marketing because of whatever reason. Now they're at this really sweet company that you like, and they're going to vouch for you because they're like, "Yeah, I worked with John, you know, five years ago. Yeah, John was a BDR, but like, he always, you know, was interested in what we're doing in product, and so we talked about stuff and I shared things with him, and like, he's really bright. Like, I would give this guy a shot."
[00:11:56] (Intro music)
[00:11:57] John Karsant: Welcome back to Prospecting Pros, and on today's show we have Matt Roberts. Welcome.
[00:12:04] Matt Roberts: Thanks for having me, John. Excited to be here.
[00:12:06] John Karsant: Yeah, so I've actually been, uh, I've seen Matt, we've been connected for a while. We've never really spoken, uh, but I've seen Matt's posts for multiple years, I think going back to when you were at Chili Piper.
[00:12:16] John Karsant: And when I was looking for guests, uh, that have a, expertise in SDRs, uh, I was looking at your profile and I thought you'd be a great fit to come on and, and talk shop.
[00:12:27] John Karsant: So, um, why don't you tell the audience a little bit about, you know, your, some of your, your previous jobs you've held, uh, and where you are today.
[00:12:35] Matt Roberts: Cool. Appreciate the time and, and the intro, John. Um, glad to see somebody's seeing the posts as well. Uh, it's been a long, a long run, so, uh, yeah.
[00:12:45] Matt Roberts: As far as my, my background goes, um, I always tell people I sort of fell into the tech sales dev, uh, world by accident. The reason I say that is I went to school, uh, UC Santa Barbara.
[00:12:57] Matt Roberts: A lot of my friends were doing something called the Technology Management Program at the time, which was, um, a lot of people ended up going into sales, product, etc., into the tech space. This was around 2013.
[00:13:08] Matt Roberts: Um, whereas I went to LA to work on music videos and reality TV. And, uh, lasted there about a year and a half, uh, little under two years.
[00:13:17] Matt Roberts: Moved back to Santa Barbara because all my buddies were there, and was pouring wine, um, and just, you know, getting by, bartending. Uh, and they'd come in on the weekends, and I would be serving my friends, and they had their, you know, fancy SDR money at the time.
[00:13:32] Matt Roberts: And they kept saying, "Hey, you got to come join us, uh, work, work with us at a startup called AppFolio." Um, there was a few different startups in Santa Barbara that were getting a little bit bigger, Procore being another one.
[00:13:42] Matt Roberts: And I just took an interview, and next thing you know, I was, I was working there and had some of the best times of my life. Early stage, you know, SDR role, working with your buddies.
[00:13:51] Matt Roberts: I always say it was very similar to the show Workaholics. We all lived together, we all worked together, uh, and it was just a really, really good time.
[00:13:58] Matt Roberts: About a year and a half into that role, um, after I'd been promoted to an AE, I got pretty burnt out and was like, "Yeah, I don't know if this is for me, and I don't know if I want to do this forever." So I quit and I traveled.
[00:14:09] Matt Roberts: Um, I was just telling you a second ago, my, my sister's in England. I did a big Euro trip for about four months with a good buddy, and came back, uh, went to my hometown up in Northern California, where is as far as, as you can get from the tech world, and was just figuring out what was next.
[00:14:26] Matt Roberts: Um, after a few, like year and a half, two years of a passion project with a buddy there, I said, "Hey, I need, I need some paychecks again." So decided to get back into the tech space because that's what I knew.
[00:14:37] Matt Roberts: And, uh, that's when I sort of like really kickstarted my career, which was, I was looking for a remote role. Um, I had the AE experience, but I was like, "I don't know if I want to be an AE again."
[00:14:46] Matt Roberts: And so I was just like, "I want to find the right company. I'll come in as an SDR, and I'll, you know, kick butt there and see where it takes me."
[00:14:53] Matt Roberts: And so I found, uh, an 18-person company that was completely remote pre-COVID called Chili Piper, uh, and said, "Hey, this looks kind of interesting. Maybe I'll apply here and, and see what happens."
[00:15:00] John Karsant: ...work with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:15:08] John Karsant: I think, you know, booking a meeting in 2019 was a lot easier than it is in 2023. And so if you're somebody who's going to give up at the, not even the first no, if you're going to give up at the 50th no or the 100th no, like this isn't the job for you.
[00:15:21] John Karsant: We also had little like weekly, and then that turned to monthly, like awards. One of them was called Animal of the Month, one of them was called Unicorn of the Month. Animal of the Month was like someone who went above and beyond. Usually it's obviously like quota-based, but if there are two or three people blowing out quota, like still it's going to be a group-voted and selected champion.
[00:15:44] John Karsant: And then the Unicorn was the person who was the most helpful. So maybe it's somebody who helped with like a call script or a sequence or a template or a new workflow with some of the tools.
[00:15:52] John Karsant: I remember trying to help like lawyers like share their screen in 2014, and it was like a pain in the ass. Like you could spend 15 minutes sometimes just trying to get them to share their screen, and like it was nuts.
[00:16:03] John Karsant: And to your point, like if someone hits me up, I go to their website and it looks like it was made in in 2005, I'm like, "All right, I'm moving on." Like it sounds crazy, but, yeah, like that stuff is so valuable.
[00:16:14] John Karsant: And I promise if you hit up 10 of them and say like, "What's up, John? Saw you work here. Would love to learn how either you broke in or just like how it's been. Like would you be down to chat for 15 minutes?"
[00:16:23] John Karsant: If you send out 10 of those, you're going to get like three or four that respond. And and all of them were in that same seat as you at one point.
[00:16:29] John Karsant: And then now when it comes to, you know, five years down the line, yeah, maybe you never worked for this person because they weren't your BDR leader, but you knew this person in product or marketing because of whatever reason. Now they're at this really sweet company that you like, and they're going to vouch for you because they're like, "Yeah, I worked with John, you know, five years ago. Yeah, John was a BDR, but like he always, you know, was interested in what we were doing in product, and so we talked about stuff and I shared things with him, and like he's really bright. Like I would give this guy a shot."
[00:16:56] Matt Roberts: Welcome back to Prospecting Pros, and on today's show we have Matt Roberts. Welcome.
[00:17:04] John Karsant: Thanks for having me, John. Excited to be here.
[00:17:06] Matt Roberts: Yeah, so I've actually been, I've seen Matt, we've been connected for a while. We've never really spoken, but I've seen Matt's posts for multiple years, I think going back to when you were at Chili Piper. And when I was looking for guests that have a expertise in SDRs, I was looking at your profile and I thought you'd be a great fit to come on and talk shop.
[00:17:28] Matt Roberts: So, why don't you tell the audience a little bit about, you know, your some of your your previous jobs you've held, and where you are today.
[00:17:35] John Karsant: Cool. Appreciate the time and the intro, John. Glad to see somebody's seeing the posts as well. It's been a long, a long run, so. Yeah, as far as my my background goes, I always tell people I sort of fell into the tech sales dev world by accident.
[00:17:53] John Karsant: The reason I say that is I went to school at UC Santa Barbara. A lot of my friends were doing something called the Technology Management Program at the time, which was, a lot of people ended up going into sales, product, etc., into the tech space. This was around 2013.
[00:18:09] John Karsant: Whereas I went to LA to work on music videos and reality TV. And lasted there about a year and a half, a little under two years. Moved back to Santa Barbara because all my buddies were there, and was pouring wine and just, you know, getting by, bartending.
[00:18:25] John Karsant: And they would come in on the weekends, and I would be serving my friends, and they had their, you know, fancy SDR money at the time. And they kept saying, "Hey, you got to come join us, work work with us at a startup called AppFolio."
[00:18:38] John Karsant: There was a few different startups in Santa Barbara that were getting a little bit bigger, Procore being another one. And I just took an interview, and next thing you know, I was I was working there and had some of the best times of my life. Early stage, you know, SDR role, working with my best buddies.
[00:18:51] John Karsant: I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:18:58] John Karsant: About a year and a half into that role, after I'd been promoted to an AE, I got pretty burnt out and was like, "Yeah, I don't know if this is for me, and I don't know if I want to do this forever." So I quit and I traveled.
[00:19:09] John Karsant: I was just telling you a second ago, my my sister's out in England. I did a big Euro trip for about four months with a good buddy, and came back, went to my hometown up in Northern California, where is as far as as you can get from the tech world, and was just figuring out what was next.
[00:19:26] John Karsant: After a few, like year and a half, two years of a passion project with a buddy there, I said, "Hey, I need I need some paychecks again." So decided to get back into the tech space because that's what I knew.
[00:19:35] John Karsant: And that's when I sort of like really kick-started my career, which was, I was looking for a remote role. I had the AE experience, but I was like, "I don't know if I want to be an AE again." And so I was just like, "I want to find the right company. I'll come in as an SDR, and I'll, you know, kick butt there and see where it takes me."
[00:19:53] John Karsant: And so I found an 18-person company that was completely remote pre-COVID called Chili Piper, and said, "Hey, this looks kind of interesting. Maybe I'll apply here and see what happens." And then long story short, got hired as SDR number three there.
[00:20:00] Matt Roberts: ...work with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time. I think, you know, booking a meeting in 2019 was a lot easier than it is in 2024.
[00:20:13] Matt Roberts: And so if you're somebody who's going to give up at the, not even the first no, if you're going to give up at the 50th no or the 100th no, like this isn't the job for you.
[00:20:21] Matt Roberts: We also had little like weekly, and then that turned to monthly, like awards. One of them was called Animal of the Month, one of them was called Unicorn of the Month. Animal of the Month was like someone who went above and beyond. Usually it's obviously like quota-based, but
[00:20:37] Matt Roberts: if there are two or three people blowing out quota, like still it's going to be a group-voted and selected champion. And then the Unicorn was the person who was the most helpful. So maybe it's somebody who helps with like a call script or a sequence or a template or a new workflow with some of the tools.
[00:20:52] Matt Roberts: I remember trying to help like lawyers like share their screen in 2014, and it was like a pain in the ass. Like you could spend 15 minutes sometimes just trying to get them to share their screen, and like it was nuts.
[00:21:03] Matt Roberts: And to your point, like if someone hits me up, I go to their website and it looks like it was made in 2005, I'm like, "All right, I'm moving on." It sounds crazy, but yeah, like that stuff is so valuable.
[00:21:14] Matt Roberts: And I promise if you hit up 10 of them and say like, "What's up, John? Saw you work here. Would love to learn how either you broke in or just like how it's been. Like would you be down to chat for 15 minutes?"
[00:21:24] Matt Roberts: If you send out 10 of those, you're going to get like three or four that respond. And all of them were in that same seat as you at one point.
[00:21:29] Matt Roberts: And then now when it comes to, you know, five years down the line, yeah, maybe you never worked for this person because they weren't your BDR leader, but you knew this person in product or marketing because of whatever reason. Now they're at this really sweet company that you like,
[00:21:43] Matt Roberts: and they're going to vouch for you because they're like, "Yeah, I worked with John five years ago. Yeah, John was a BDR, but like he always, you know, was interested in what we were doing in product, and so we talked about stuff and I shared things with him and like he's really bright, like I would give this guy a shot."
[00:21:57] John Karsant: Welcome back to Prospecting Pros and on today's show we have Matt Roberts. Welcome.
[00:22:04] Matt Roberts: Thanks for having me, John. Excited to be here.
[00:22:06] John Karsant: Yeah, so I've actually been, I've seen Matt, we've been connected for a while. We've never really spoken, but I've seen Matt's posts for multiple years, I think going back to when you were at Chili Piper. And when I was looking for guests that have a expertise in SDRs,
[00:22:21] John Karsant: I was looking at your profile and I thought you'd be a great fit to come on and talk shop. So why don't you tell the audience a little bit about some of your previous jobs you've held and where you are today.
[00:22:35] Matt Roberts: Cool. Appreciate the time and the intro, John. Glad to see somebody's seeing the posts as well. It's been a long run, so yeah.
[00:22:45] Matt Roberts: As far as my background goes, I always tell people I sort of fell into the tech sales dev world by accident. The reason I say that is I went to school at UC Santa Barbara. A lot of my friends were doing something called the Technology Management Program at the time, which was
[00:23:01] Matt Roberts: a lot of people ended up going into sales, product, etc., into the tech space. This was around 2013. Whereas I went to LA to work on music videos and reality TV.
[00:23:13] Matt Roberts: And lasted there about a year and a half, little under two years. Moved back to Santa Barbara because all my buddies were there and was pouring wine and just, you know, getting by, bartending.
[00:23:25] Matt Roberts: And they'd come in on the weekends and I would be serving my friends and they had their, you know, fancy SDR money at the time.
[00:23:33] Matt Roberts: And they kept saying, "Hey, you got to come join us, work with us at a startup called AppFolio." There was a few different startups in Santa Barbara that were getting a little bit bigger, Procore being another one. And I just took an interview and next thing you know, I was working there
[00:23:47] Matt Roberts: and had some of the best times of my life. Early stage, you know, SDR role, working with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together,
[00:23:58] Matt Roberts: and it was just a really, really good time. About a year and a half into that role, after I'd been promoted to an AE, I got pretty burnt out and was like, "I don't know if this is for me and I don't know if I want to do this forever." So I quit and I traveled.
[00:24:10] Matt Roberts: I was just telling you a second ago, my sister's in England. I did a big Euro trip for about four months with a good buddy and came back, went to my hometown up in Northern California where is as far as you can get from the tech world,
[00:24:25] Matt Roberts: and was just figuring out what was next. After a few, like a year and a half, two years of a passion project with a buddy there, I said, "Hey, I need some paychecks again." So decided to get back into the tech space because that's what I knew.
[00:24:41] Matt Roberts: And that's when I sort of like really kickstarted my career, which was I was looking for a remote role. I had the AE experience, but I was like, "I don't know if I want to be an AE again." And so I was just like, "I want to find the right company. I'll come in as an SDR and I'll,
[00:24:54] Matt Roberts: you know, kick butt there and see where it takes me." And so I found an 18-person company that was completely remote pre-COVID called Chili Piper and said, "Hey, this looks kind of interesting. Maybe I'll apply here and see what happens."
[00:25:00] Matt Roberts: ...work with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time. I think, you know, booking a meeting in 2019 was a lot easier than it is in 2023.
[00:25:14] Matt Roberts: Um, and so if you're somebody who's going to give up at the, not even the first no, if you're going to give up at the 50th no or the 100th no, like this isn't the job for you.
[00:25:21] Matt Roberts: We also had little like weekly, and then that turned to monthly, um, uh, like awards. One of them was called Animal of the Month, one of them was called, uh, Unicorn of the Month. Animal of the Month was like someone who went above and beyond. Usually it's obviously like quota-based, but, um, if there are two or three people blowing out quota, like still it's going to be a group, uh, voted, um, and selected champion.
[00:25:44] Matt Roberts: And then the Unicorn was the person who was the most helpful. So maybe it's somebody who helped with like a call script or a sequence or a template or a new workflow, uh, with some of the tools.
[00:25:52] Matt Roberts: I remember trying to help like lawyers like share their screen in 2014, and it was like a pain in the ass. Like you could spend 15 minutes sometimes just trying to get them to share their screen, and like it was nuts.
[00:26:03] Matt Roberts: And to your point, like if someone hits me up, I go to their website and it looks like it was made in, in 2005, I'm like, "All right, I'm moving on." Like, sounds crazy, but, um, yeah, like that stuff is so valuable.
[00:26:14] Matt Roberts: And I promise if you hit up 10 of them and just say like, "What's up, John? Saw you work here. Would love to learn how either you broke in or just like how it's been, like would you be down to chat for 15 minutes?" If you send out 10 of those, you're going to get like three or four that respond. And, and all of them were in that same seat as you at one point.
[00:26:29] Matt Roberts: And then now when it comes to, you know, five years down the line, yeah, maybe you never worked for this person because they weren't your BDR leader, but you knew this person in product or marketing because of whatever reason. Now they're at this really sweet company that you like, and they're going to vouch for you because they're like, "Yeah, I worked with John, you know, five years ago. Yeah, John was a BDR, but like he always, you know, was interested in what we were doing in product, and so we talked about stuff and I shared things with him, and like he's really bright. Like I would give this guy a shot."
[00:26:56] John Karsant: Welcome back to Prospecting Pros, and on today's show we have Matt Roberts. Welcome.
[00:27:04] Matt Roberts: Thanks for having me, John. Excited to be here.
[00:27:06] John Karsant: Yeah, so I've actually been, uh, I've seen Matt, we've been connected for a while. We've never really spoken, uh, but I've seen Matt's posts for multiple years, I think going back to when you were at Chili Piper. And when I was looking for guests, uh, that have a, expertise in SDRs, uh, I was looking at your profile and I thought you'd be a great fit to come on and, and talk shop.
[00:27:27] John Karsant: So, um, why don't you tell the audience a little bit about, you know, your, some of your, your previous jobs you've held, uh, and where you are today.
[00:27:35] Matt Roberts: Cool. Appreciate the time and, and the intro, John. Um, glad to see somebody's seeing the posts as well. Uh, it's been a long, a long run, so, uh, yeah. As far as my, my background goes, um, I always tell people I sort of fell into the tech sales dev, uh, world by accident.
[00:27:53] Matt Roberts: The reason I say that is I went to school, uh, UC Santa Barbara. A lot of my friends were doing something called the Technology Management Program at the time, which was, um, a lot of people ended up going into sales, product, etc., into the tech space. This was around 2013. Um, whereas I went to LA to work on music videos and reality TV.
[00:28:13] Matt Roberts: And, uh, lasted there about a year and a half, uh, little under two years. Moved back to Santa Barbara because all my buddies were there, and was pouring wine, um, and just, you know, getting by, bartending. Uh, and they'd come in on the weekends, and I would be serving my friends, and they had their, you know, fancy SDR money at the time.
[00:28:33] Matt Roberts: And they kept saying, "Hey, you got to come join us, uh, work, work with us at a startup called AppFolio." Um, there was a few different startups in Santa Barbara that were getting a little bit bigger, Procore being another one. And I just took an interview, and next thing you know, I was, I was working there and had some of the best times of my life.
[00:28:48] Matt Roberts: Early stage, you know, SDR role, working with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, uh, and it was just a really, really good time.
[00:28:58] Matt Roberts: About a year and a half into that role, um, after I'd been promoted to an AE, I got pretty burnt out and was like, "I don't know if this is for me, and I don't know if I want to do this forever." So I quit and I traveled. Um, I was just telling you a second ago, my, my sister's out in England. I did a big Euro trip for about four months with a good buddy, and came back, uh, went to my hometown up in Northern California, where is as far as, as you can get from the tech world, and was just figuring out what was next.
[00:29:26] Matt Roberts: Um, after a few, like year and a half, two years of a passion project with a buddy there, I said, "Hey, I need, I need some paychecks again." So decided to get back into the tech space because that's what I knew. And, uh, that's when I sort of like really kick-started my career, which was, I was looking for a remote role.
[00:29:43] Matt Roberts: Um, I had the AE experience, but I was like, "I don't know if I want to be an AE again." And so I was just like, "I want to find the right company. I'll come in as an SDR, and I'll, you know, kick butt there and see where it takes me." And so I found, uh, an 18-person company that was completely remote pre-COVID called Chili Piper, uh, and said, "Hey, this looks kind of interesting. Maybe I'll apply here and see what happens."
[00:30:00] Matt Roberts: ...and then long story short, got hired as SDR number three there, um, and within about six months I was the SDR manager...
[00:30:00] John Karsant: ...work with your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:30:08] John Karsant: I think, you know, booking a meeting in 2019 was a lot easier than it is in 2026.
[00:30:13] John Karsant: And so if you're somebody who's going to give up at the—not even the first no—if you're going to give up at the 50th no or the 100th no, like this isn't the job for you.
[00:30:21] John Karsant: We also had little like weekly, and then it turned to monthly, like awards. One of them was called Animal of the Month, one of them was called Unicorn of the Month. Animal of the Month was like someone who went above and beyond. Usually it's obviously like quota-based, but if there are two or three people blowing out quota, like still it's going to be a group-voted and selected champion. And then the Unicorn was the person who was the most helpful. So maybe it's somebody who helps with like a call script, or a sequence, or a template, or a new workflow with some of the tools.
[00:30:52] John Karsant: I remember trying to help like lawyers like share their screen in 2014, and it was like a pain in the ass. Like you could spend 15 minutes sometimes just trying to get them to share their screen, and like it was nuts.
[00:31:03] John Karsant: And to your point, like if someone hits me up, I go to their website and it looks like it was made in 2005, I'm like, "All right, I'm moving on." Like, sounds crazy, but yeah, like that stuff is so valuable.
[00:31:14] John Karsant: And I promise if you hit up 10 of them and say like, "What's up, John? Saw you work here. Would love to learn how either you broke in or just like how it's been. Like, would you be down to chat for 15 minutes?" If you send out 10 of those, you're going to get like three or four that respond. And all of them were in that same seat as you at one point.
[00:31:29] John Karsant: And then now when it comes to, you know, five years down the line, yeah, maybe you never worked for this person because they weren't your BDR
[Warning: Gemini stopped because this chunk reached the max token limit. This segment may be incomplete.]
[00:35:00] Matt Roberts: ...work with some of your buddies. I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:35:08] Matt Roberts: I think, you know, booking a meeting in 2019 was a lot easier than it is in 2026. And so if you're somebody who's going to give up at the, not even the first no, if you're going to give up at the 50th no or the 100th no, like this isn't the job for you.
[00:35:21] Matt Roberts: We also had little like weekly, and then it turned to monthly, uh, like awards. One of them was called Animal of the Month, one of them was called, uh, Unicorn of the Month. Animal of the Month was like someone who went above and beyond. Usually it's obviously like quota-based, but, um, if there are two or three people blowing out quota, like still it's going to be a group, uh, voted, um, and selected champion.
[00:35:44] Matt Roberts: And then the Unicorn was the person who was the most helpful. So maybe it's somebody who helps with like a call script or a sequence or a template or a new workflow, uh, with some of the tools.
[00:35:52] Matt Roberts: I remember trying to help like lawyers like share their screen in 2014, and it was like a pain in the ass. Like you could spend 15 minutes sometimes just trying to get them to share their screen, and like it was nuts.
[00:36:03] Matt Roberts: And to your point, like if someone hits me up, I go to their website and it looks like it was made in, in 2005, I'm like, "All right, I'm moving on." Like, sounds crazy, but, um, yeah, like that stuff is so valuable.
[00:36:14] Matt Roberts: And I promise if you hit up 10 of them and say like, "What's up, John? Saw you work here. Would love to learn how either you broke in or just like how it's been, like would you be down to chat for 15 minutes?"
[00:36:23] Matt Roberts: If you send out 10 of those, you're going to get like three or four that respond. And, and all of them were in that same seat as you at one point.
[00:36:29] Matt Roberts: And then now when it comes to, you know, five years down the line, yeah, maybe you never worked for this person because they weren't your BDR leader, but you knew this person in product or marketing because of whatever reason. Now they're at this really sweet company that you like, and they're going to vouch for you because they're like, "Yeah, I worked with John, you know, five years ago. Yeah, John was a BDR, but like he always, you know, was interested in what we were doing in product, and so we talked about stuff and I shared things with him, and like he's really bright. Like I would give this guy a shot."
[00:36:56] John Karsant: Welcome back to Prospecting Pros, and on today's show we have Matt Roberts. Welcome.
[00:37:04] Matt Roberts: Thanks for having me, John. Excited to be here.
[00:37:06] John Karsant: Yeah, so I've actually been, I've seen Matt, we've been connected for a while. We've never really spoken, but I've seen Matt's posts for multiple years, I think going back to when you were at Chili Piper. And when I was looking for guests that have a expertise in SDRs, I was looking at your profile and I thought you'd be a great fit to come on and talk shop.
[00:37:28] John Karsant: So, why don't you tell the audience a little bit about some of your previous jobs you've held and where you are today.
[00:37:35] Matt Roberts: Cool. Appreciate the time and the intro, John. Glad to see somebody's seeing the posts as well. It's been a long, a long run, so. Yeah, as far as my background goes, um, I always tell people I sort of fell into the tech sales dev world by accident.
[00:37:53] Matt Roberts: The reason I say that is I went to school at UC Santa Barbara. A lot of my friends were doing something called the Technology Management Program at the time, which was a lot of people ended up going into sales, product, etc., into the tech space. This was around 2013.
[00:38:09] Matt Roberts: Whereas I went to LA to work on music videos and reality TV. And lasted there about a year and a half, a little under two years. Moved back to Santa Barbara because all my buddies were there, and was pouring wine, um, and just, you know, getting by, bartending.
[00:38:25] Matt Roberts: And they would come in on the weekends, and I would be serving my friends, and they had their, you know, fancy SDR money at the time. And they kept saying, "Hey, you got to come join us, work with us at a startup called AppFolio."
[00:38:38] Matt Roberts: There was a few different startups in Santa Barbara that were getting a little bit bigger, Procore being another one. And I just took an interview, and next thing you know, I was working there and had some of the best times of my life. Early stage, you know, SDR role, working with your buddies.
[00:38:51] Matt Roberts: I always say it was very similar to the show Workaholics. We all lived together, we all worked together, and it was just a really, really good time.
[00:38:58] Matt Roberts: About a year and a half into that role, after I'd been promoted to an AE, I got pretty burnt out and was like, "I don't know if this is for me, and I don't know if I want to do this forever." So I quit and I traveled.
[00:39:10] Matt Roberts: I was just telling you a second ago, my sister's in England. I did a big Euro trip for about four months with a good buddy, and came back, went to my hometown up in Northern California, where is as far as you can get from the tech world, and was just figuring out what was next.
[00:39:28] Matt Roberts: After a few, like year and a half, two years of a passion project with a buddy there, I said, "Hey, I need, I need some paychecks again." So decided to get back into the tech space because that's what I knew.
[00:39:37] Matt Roberts: And that's when I sort of like really kick-started my career, which was I was looking for a remote role. I had the AE experience, but I was like, "I don't know if I want to be an AE again." And so I was just like, "I want to find the right company. I'll come in as an SDR, and I'll, you know, kick butt there and see where it takes me."
[00:39:53] Matt Roberts: And so I found an 18-person company that was completely remote pre-COVID called Chili Piper, and said, "Hey, this looks kind of interesting. Maybe I'll apply here and see what happens."
