Listen on YouTube // Apple // Spotify

Who you’ll learn from

Chris McDonough has joined 4 companies right before they exploded. At the first, Motive, he was employee 40 and watched revenue go from $800K to $30M in about 100 days. The VP of Sales at Campfire joins Sophie Buonassisi on GTMnow to break down what he learned riding hypergrowth over and over, and why he thinks AI is about to split the sales profession in two.

Chris gets tactical on the whole arc: how a two-week decision to sign a lease and move to SF changed his trajectory, what a federal mandate taught him about compelling events, why your career growth is tied directly to how fast your company grows, and how he now builds an AI-native sales org from scratch at Campfire (an AI-native ERP taking on the legacy giants). He also makes the contrarian case that AI won’t replace reps but will widen the gap between them, why AI outbound is mostly spam for complex B2B, and why a strong SDR bench is existential.

What you’ll learn:

  • The $800K-to-$30M-in-100-days story, and what a compelling event really looks like
  • Why your career trajectory is tied to your company’s growth rate (”you can’t be a VP if there’s no one to be VP of”)
  • The contrarian AI take: not labor replacement, but a top 30% worth triple and a bottom 20% that’s hard to employ
  • What he hires for now: not just skill, but whether you can self-learn from AI on day one
  • How to build an AI-native sales org with no tech debt (the deal dashboard that grades every call against every win and loss)
  • Why AI outbound mostly becomes a spam tool in complex B2B, and why the SDR bench matters more
  • Why he leaves once a company is big enough to run Workday, and goes back downmarket
  • How to sell into the “real economy,” where nobody cares about your hot VC and references are hyper-local
  • Regrettable churn: the retention metric behind Samsara’s run, and why top reps compound
  • One-way vs. two-way doors: how to make fast decisions at 70-80% of the data

Episode highlights

01:17 – Welcome, and a career of joining companies right before they explode

01:51 – Employee 40 at Motive, and the two-week decision that changed everything

04:19 – The federal mandate, and the hiring class that got promoted in 30 days

05:33 – Why career growth is tied to company growth rate

07:12 – The mandate story: from selling nothing to 70 demos a week

10:19 – Was it the wrong decision? Believing through the objection

10:56 – What 800-900 demos in 3 months does to a seller

12:11 – Samsara: scaling an office 0 to 100, and 250 interviews in 90 days

13:42 – The contrarian hiring philosophy: the 10x seller and the widening gap

15:59 – Why he left Rippling for Campfire, and the “Workday rule”

18:41 – Building an AI-native sales org with no tech debt

21:14 – What Campfire is: AI-native ERP and one of software’s last moats

25:25 – Expanding the TAM and the recession-proof case

26:12 – Selling into the real economy: hyper-local references, not hot logos

28:26 – His honest take on AI outbound and AI SDRs

30:49 – The SDR org as your existential talent bench

31:56 – The metric he obsesses over: regrettable churn

33:45 – Who Campfire is hiring, and “will Claude kill this company?”

35:33 – Rapid fire: leadership, execution over competitors, one-way vs. two-way doors

40:19 – Where to find Chris, and how to actually DM your way into a job

Key takeaways

1. Your career trajectory is tied to your company’s growth rate, so join the explosion.
Chris joined Motive (then KeepTruckin) as employee 40 and took the hiring class starting in two weeks instead of six. That single choice compounded enormously: everyone in his class was promoted to AE in 30 days, while the six-weeks-later class waited 18 months. In that same window he went from SDR to interim director running a large team in Nashville. His blunt advice: assuming equal talent and work ethic, the fastest way to accelerate a career is joining a company in hypergrowth, because “you can’t be a VP if there’s no one to be a VP of.” New markets, new segments, and leadership seats only open when the company is expanding fast.

2. Reps and volume build the muscle, and a compelling event is gold.
Motive sold almost nothing from May to September 2017 because truckers believed the incoming administration would kill the federal ELD mandate (it never was in doubt). Chris held conviction through the objection because he didn’t believe it was real. When the December deadline got real, demand became insatiable: he did 70+ demos a week, blocked his calendar just to eat and use the bathroom, and the company went from $800K to $30M in about 100 days (roughly $100M by the time he left). The lesson beyond the number: a legally mandated purchase is the ultimate compelling event, and doing 800-900 demos in three months compressed years of rep-building into weeks.

3. AI won’t replace reps, it’ll widen the gap, and that reshapes hiring.
Chris’ contrarian belief mirrors the “10x engineer” becoming the “100x engineer”: AI makes top performers exponentially more productive, so he expects a core 30% of salespeople worth triple everyone else and a bottom 20% who become hard to employ. That changed what he hires for. Raw skill and work ethic still matter, but the differentiator now is whether someone can self-learn: at Campfire, Claude is wired into everything, so a new rep can mine calls, demos, and insights on day one instead of waiting for knowledge locked in someone’s head. He’s also candid that he left Rippling partly out of a personal fear he wasn’t developing AI-native skills fast enough to stay employable, the same fear he thinks reps everywhere should take seriously.

4. Building AI-native means no tech debt and ruthless tool integration.
Starting fresh at Campfire, Chris designs the stack around how tools talk to each other, testing the quality of each tool’s MCP and assuming most will become “headless.” His flagship example: an automation that listens to every call, enriches the deal in the CRM via Clay, and grades it against every closed-won and closed-lost deal the company has ever had, producing a daily top-deal dashboard tied to battle cards that also flags when a champion leaves or a new VP appears. It kills the two-hour manual QBR deck, because every call is already listened to and every deal already scored, freeing managers to coach faster. On the business itself: he argues ERP is one of software’s last moats because the data is audited and correct (unlike messy CRM data), which makes it both defensible from “will Claude build this?” fears and a strong long-term foundation for AI workflows.

5. Build a strong SDR bench and obsess over regrettable churn.
Chris is skeptical of AI outbound: in complex B2B it mostly becomes a spam tool with very low conversion, useful only for transactional/low-end deals. The companies that win, in his view, invest in a real SDR org that becomes the talent bench, his ideal is hiring an SDR he promotes to director years later (at Rippling, nine of twelve directors were once AEs). Internal promotes ramp faster, attain higher, and are less risky, and a visible promotion track is a recruiting magnet. The metric he tracks most fiercely beyond revenue and pipeline is regrettable churn: he credits Samsara’s $100M-to-$1B IPO run to barely losing a single top rep, because top performers compound over years (the top 30-40% often carry 70-80% of the number). Two bonus frames worth stealing: sell into the “real economy” with hyper-local references (an oil-and-gas buyer in Texas wants to hear about another Texas oil-and-gas customer, not your hot SF logo), and use Bezos’ one-way vs. two-way door test to move fast at 70-80% of the data.

Chris McDonough

Sophie Buonassisi (Host)

The GTMnow Newsletter (by GTMfund)
GTMnow merges go-to-market strategy, venture capital and media.
Build, scale and invest with the best minds in tech.

The media brand of VC firm, GTMfund – sharing the how and who behind company growth.

GTMnow

The GTMnow Podcast – subscribe to support

It would mean the world to us if you subscribe to the show on your platform of choice. This helps support our growth, which in turn helps us continuously bring on bigger guests and deliver the content that you want to hear most.

The GTMnow Podcast shares how the best in tech build, scale and invest.

Visit gtmnow.com for more episodes, The GTMnow Newsletter editions, and other content.

GTMnow is run by GTMfund, an early-stage venture firm made up of 350+ go-to-market executives from the fastest-growing companies.

Full Episode Transcript

00:00 – 00:05

Sophie Buonassisi: How did you end up as employee 40 of this company before it went through a huge growth explosion?

00:05 – 00:27

Chris McDonough: I was doing over 70 demos a week, so like effectively we went from 800 K, $30 million in revenue in about 100 days. Everyone that was in my hiring class as an STR was promoted in 30 days to 80. By the time they got promoted as an AI. I had already moved to Nashville. I had opened up an office and I was managing manager. One decision to like, sign a lease in the living room to move in two weeks fundamentally changed my entire career.

00:27 – 00:32

Sophie Buonassisi: Chris McDonough, vice president of sales at campfire, give us their secret sauce of how do you pick the right reps?

00:32 – 00:53

Chris McDonough: The difference between top performer and bond former is going to be exponential. So I think like you’re going to have this core 30% of salespeople that are worth like triple of everyone else, and then the bottom 20% are going to be very tough to employ. The great thing about campfire is we’re in SF and we’ve built a tremendous business, tech and AI. We have some like the hottest logos very soon in the future that if you don’t know how to use AI, you’re going to be effectively unemployable.

00:53 – 01:02

Sophie Buonassisi: There’s a lot of talk around AI outbound, AI SDRs. I gotta ask you, when you hear that, like, what’s your honest reaction?

01:17 – 01:19

Sophie Buonassisi: Chris, welcome to GTM now.

01:19 – 01:20

Chris McDonough: Thank you.

01:20 – 01:51

Sophie Buonassisi: I’m excited to be here. I’m excited to have you here. And now you’ve joined four companies right before they went on to have some incredible growth trajectories. Currently, you’re the VP of sales at campfire, which is no pun intended, like on fire in a good way, in the good sense. But before that you also joined samsara through hyperscale periods and Motiv. So let’s start from the beginning, which was Motiv. You were employee 40. How did you end up as employee 40 of this company before it went through a huge growth explosion?

01:51 – 04:05

Chris McDonough: Yeah. I think the most interesting thing about Motiv and the little background on me is like, I’m born and raised in Florida. I’m from a really small town in at Daytona Beach. It’s only really known for NASCAR in spring break. So where I come from, no one ever thought of tech. I didn’t even know what SaaS was in 2017. I never even heard the word before. And so growing up, my my family owned a small printing company. So I there was like this idea I would go take that over, I would do after college. Very quickly, I realized that was not the path for me. And so living in Florida, trying to figure out what to do, where to go, what to do next. And back in 2017. Like Snapchat was like the hot app. Everyone was on it. And so I saw a person that, ironically, I barely knew I went to college with, and I saw that he had moved from Florida to SF, and he was posted by his job and he posted some some cool videos. So I shot him a text over Snapchat. I was like, how’d you end up there? He’s like, oh, actually, I met with this recruiting firm. They got me a job, they placed me and I moved, and so he sent me the intro, met with a recruiting firm. A couple weeks later, I’m in SF. I meet with motive at the time, Keep Trucking before they rebranded, and they gave me a job offer. And the most interesting part about it was the pitch was for those that aren’t really aware of motive in samsara is they were born before a federal mandate came into place. And so the effective thing was like nobody had a thing and then everyone was legally mandated by it. And so the bitch was like, come to SF, we have this new product that’s legally mandated and no one has it yet. And so you’re going to have to go do it. And so once I pitched, sounded great to me. It’s hard to talk about compelling event in a sales cycle. If you legally have to buy something or you’re put out of business as a, it’s a good thing to have. And so I was given two options. It was like, hey, we got two hiring classes, either starting two weeks or starting six weeks. And so I was in SF, I got the job offer while I was there, and I just made a decision like, I’m gonna do the two weeks. I was very blessed. I didn’t have like a lease or anything. And then that weekend, you know, the at the time I was very early in career, did not have a lot of money, and so I ended up renting a living room with a partition that actually came with a thing. I’m not sure if you’re aware of what a loft bed is, okay, it’s effectively a bunk bed without a bottom bunk for like a fish. See, purpose is the only thing I could afford. Yeah, so I found this thing. Especially in 2017. The real estate market was really hot. So. Yeah.

04:05 – 04:05

Sophie Buonassisi: And two weeks?

04:05 – 04:17

Chris McDonough: No, exactly. I got signed the lease. Um, everyone told me I was insane. So two weeks later, I joined. And the most interesting thing about that, and something that’s like, stayed with me my entire career, is

04:19 – 05:20

Chris McDonough: we’re at the cusp of this explosion with this federal mandate. And so everyone that was in my hiring class as an STR was promoted in 30 days to AI. And so it was like we did not even go off ramp. We just started learning the tools like, hey, we need you guys are here, get after it. And then the people that joined at the six week mark, they didn’t get promoted for 18 months. Oh, wow. And so in the time that the people in that hiring class, there was an opportunity for them to get promoted. By the time they got promoted as an AI, I had already moved to Nashville. I had opened up an office and I was managing managers. So in 18 months I went from SDR to like interim director running like a large team before those people even had the opportunity to become an A, and so it’s like it’s always sat with me in terms of like what could have been, what couldn’t have been and how like that one decision to, like, sign a lease in a living room to move in two weeks, like, fundamentally changed my entire career. And I think I would not be in the place I am today if I didn’t make that decision.

05:20 – 05:33

Sophie Buonassisi: I guess you said it stays with you. Like, what advice would you then have? And maybe it’s not exactly. Hey, move within two weeks and stay in a loft bed. But like, what does that give you when you are now mentoring younger salespeople?

05:33 – 07:00

Chris McDonough: Yeah. And it’s I mean, it’s obviously mentoring, but it’s like in the hiring process, like we’re seriously startup, we’re hot, we raise a bunch of money, but like it’s still risk for small company, especially for folks that are like larger companies. It’s like, hey, I feel very safe. Ricotta or samsara, like, those are very safe companies. They’re hardware based. So they have a moat from an AI. Like they’re not going to be disrupted by AI at this stage. But my biggest advice to people is like assuming all things else are equal. If you’re smart, intelligent, hard working. The biggest way for you to expedite your growth and your career is joining a company that’s in hyper. Your career trajectory, assuming all things else are equal, is completely tied to how fast the company is growing, how many products, how many people they’re hiring. You can’t become a VP if there’s no one to be a VP of. And so then, like, I’m hiring a bunch of people. Like, even when I, when I came and campfire, we’re hiring, we’re scaling. We had two phenomenal Founding A’s who’ve done a phenomenal job like building out campfire came in, realized we needed it. I promoted both up the manager in two weeks. And so now they’re managers. Now they’re leading teams, places like at samsara. It’s two years from start to non-negotiable. Yeah. And so like by taking the risk going early stage like it won’t always work out. But like that exponential growth is what drives your career. That gives you opportunities. New markets, new countries, new segments, leadership. You’re not growing like they’re not going to open up an office in APAC and you won’t have an opportunity to go to Australia or go to London and stuff like that. It’s always tied to Hypergrowth in my eyes.

07:00 – 07:12

Sophie Buonassisi: I love it, that is great advice, if you will. And you mentioned there was this regulatory mandate. So when you joined motive, it was right before this insane explosive growth. Tell us about what happened.

07:12 – 10:03

Chris McDonough: Yeah. And so effectively with with Motive Truckers um, were recording how many hours they drove by hand. They look a little book and they filled it out. So you can imagine. And what happened was how many hours you drove, you had to take a break and you had, like, stop for 10 to 12 hours. Obviously people were not doing that because you could race it. They had multiple books and so drivers could be driving for a day straight. It’s very unsafe. A trucker, a trucking, especially like a think about an oil tanker. Yeah, like a 60. It’s a 60,000 pound missile driving down the street. It’s very dangerous if done in safely. And so when I joined, I joined in May. The mandate went into effect in December. And so it was a very interesting time because this was right when right after the election and when this was an Obama era mandate that his government like, put together, it’s like, hey, the fmcsa, this is what we’re going to do. And so obviously, like when Trump was coming to office, his pitch was like, we’re going to knock down regulation, we’re going to do all these things. So when we were cold calling into the market, we’re cold calling the truck companies and rural parts of America. So obviously, like they really align with that. And so the objection was, hey, actually we don’t believe in this. Trump’s going to get rid of it when that was never talked about. There’s not an article. There was no inkling that this mandate was going to get overturned. But the entire Tam believed that. And so from May to roughly like August, September, we almost sold nothing we luckily had raised from Google Ventures that are series B. We were at $800,000 in revenue. Things weren’t moving. We were building pipeline. We were having demos. But it was like, hey, like, we actually don’t believe this is happening, so we’re not going to buy it. So it’s like it came into effect on December 17th. The famous line was coming 17th. And so then like September hits and then everyone starts to freak out because like, oh, this, this is real. And also yeah, remember it’s it’s hardware. Yeah. And so you have to get it and you have to install it. And also it’s hardware is inventory. And so for us like there was this huge debate on how much inventory to have because like we’re not selling we’re being pipe. And so what are we going to do. And so then it just hit the fan. And so we went from selling nothing to doing. I was doing over 70 demos a week. I had to put blocks on my calendar to get coffee, go to the bathroom, get lunch, because there was so much inbound that SDR was booking a meeting of every minute of every day, and this went on for like three plus months. There was even a phone line. If you wanted to work on the weekends, where you could take calls and demos and move units because the demand was insatiable, they legally had to buy it and the entire Tam waited till the very last minute and so like effectively we went from 800 K to $30 million in revenue in about 100 days. So it was just like exponential.

10:04 – 10:19

Sophie Buonassisi: Yeah, that is explosive growth. And I mean, it must have been weird to joining the company at 800 K, having been promised, you know, this roller, that this regulation would come into effect and then just not seeing any revenue come in the door. Did you ever feel nervous that maybe it was the wrong decision?

10:19 – 10:42

Chris McDonough: I didn’t I did it because, like, I fundamentally didn’t believe in the objection. Yeah. It’s like we knew we were going to sell. The question was how much we ran out of inventory. No one could have guessed that that would have happened in terms of like 70 demos nonstop. Everyone was working like 100 hours a week. I knew something was going to happen. I didn’t know that was going to happen. Yeah, like that was like no one did.

10:42 – 10:44

Sophie Buonassisi: 800 K yeah. 230 million.

10:44 – 10:47

Chris McDonough: Correct. That’s 100 days. 2017 it was uncommon.

10:48 – 10:56

Sophie Buonassisi: Yeah. And so I mean, you were taking you mentioned 70 demos per week. Like, what did that do for yourself as? As a seller too?

10:56 – 11:53

Chris McDonough: Yeah, I think what was really interesting about that is like when you think about it, it’s obviously like inbound is substantial, easier than outbound. But like so much of sales, it’s it’s just like going to the gym. It’s reps. And so at that stage in the three month period, like, I mean we did maybe like 800, 900 demos and that’s for demos. And some people do like because right now the average sales org like you’re, you’re probably doing like ten demos a month if you’re like super busy. Yeah. Maybe 20. And so we were doing 4 to 5 x what someone would do in a month, in a week. And so I think for all of us it like expedited all of our growth. Because like you just going through the motions, you’re giving pitches, you’re taking objections, you’re closing deals, you’re going through the red lines. And so then, like, you exponentially have gone through more sales cycles than most people have gone through in five, even ten years. And so although there was some level of easiness due to like, compelling event, it’s still something that builds that muscle that like would have taken much longer. Else wise otherwise.

11:53 – 12:10

Sophie Buonassisi: Yeah. It sounds like your career. I mean, at this early stage, too, it was just an explanation of everything in terms of timeline, in terms of reps, everything. And that is just the compounding effect of that is incredible. And so then after motive, I mean, you joined at 800 K. What was the revenue when you left?

12:10 – 12:11

Chris McDonough: Roughly 100 million.

12:11 – 12:27

Sophie Buonassisi: Roughly 100 million, including that kind of $30 million, 100 day sprint. You went on to join samsara Berkata through hyperscale periods of their own, right. Do you have any key sales lessons from either or both of those experiences?

12:27 – 13:37

Chris McDonough: Yeah, because I think before I left motive, I moved to Nashville to open up that office, and it was samsara moved to Atlanta to open up their office. And I joined like we joined a haunted mill. It was right when the like Andresen like $200 million hit. And so then it was like time to go. Yeah. And so we scaled that office from like 0 to 100 people. It’s funny, it’s kind of similar to that. Like we had a Tableau dashboard that we were held accountable to for recruiting because like the main goal was like, you guys have to hire like every leader is like very much baked into their day to day. So we were tracking like, how many phone screens you were doing, how many demos like you were expected to like, go recruit. We need to hire like 100 people. And all of us that were in that founding leadership team, we did 250 interviews in like our first 90 days. So like what I learned there was like how to hire, how to pick talent. And like, especially with that office in Atlanta, scaling like in a non-core market. The biggest thing I learned was like the importance of like hiring, developing and retaining top talent and how to do that, how to pick the right people. Because we obviously when you hire that quick, you’re going to make misses. Yeah. Is this inevitable? You can’t put that many people into a room that quickly without making some mistakes. So there’s a lot of lessons there.

13:37 – 13:42

Sophie Buonassisi: And if you could boil it down, maybe give us your secret sauce of how do you pick the right reps.

13:42 – 15:51

Chris McDonough: It depends on the company, right? It depends on the role, what they’re doing, how they’re doing it. Because we’re able to hire terracotta or very different. The ramps of the reps I would hire at campfire. Yeah. So I think my core philosophy right now is I have like a contrarian belief. And what it is is that a lot of people think that a lot of things are going to be automated by AI, and we’re going to have labor replacement. And like CES and AI’s, I actually think the opposite. You’ve seen it with engineers already. You have the ten engineer now it’s like the 100 x engineer where it’s like there’s so much exponentially more productive that you see the salaries that engineers are getting now. It’s because, like, they’re going to go do 20 x. So you can give five people salaries to one person. We’re not quite there yet. But I do think you’re going to have like the ten x sales person. And so I think like with AI and your ability to like self-serve your own knowledge onboarding training, when you enter these AI native companies, the difference between a top performer and a bond former is going to be exponential. So I think like you’re going to have this core 30% of salespeople that are worth like triple of everyone else, and then the bottom 20% are going to be very tough to employ. And so what I’m looking for now, especially at campfire, it’s like, how intelligent are you? Are you hard working? How are you going to solve problems? But also like, what I’m really curious about is how they are going to seek and develop feedback. Because now when you join a company, that campfire day one, we’re built with AI in mind. And so we have clod. That’s MC speed and absolutely every single thing in the business. And so when you join day one you can go into cloud and just look for calls, look for demos, get insights. Your ability to go find information to improve like your own skills is exponential. First, if you join a company 2017 like where is it at? It’s written down. It’s in someone’s head. Like you have to go. Like someone has to actually sit down and give you that information. Yeah. And so now I’m looking for people that not just are good sellers or not just hardworking, but like, those people are going to become, over time, substantially more productive than everyone else. And we’re still an early stage startup. We don’t have, like, everything all figured out. And so it’s like, how can these people self learn, self develop? And I think that’s going to be the difference maker of the next two years for people that are joining these companies.

15:51 – 15:59

Sophie Buonassisi: And Chris, it was just this year that you actually left for Qatar and joined campfire. Correct. Why the shift? Like why did you leave?

15:59 – 16:22

Chris McDonough: Yeah, because I think for me ricotta is incredible company, incredible product. Like really game changer. But ricotta just had 5000 employees. They’re doing over a billion a year in net new revenue. They’re past the scale up stage. It’s pretty relevant for me now. Selling campfire, which is ERP, is like my joke. And it actually applied samsara to is like typically when a company gets large enough to implement workday, it’s typically time for me to leave it.

16:22 – 16:23

Sophie Buonassisi: Good rule.

16:23 – 18:27

Chris McDonough: Of thumb. It’s too large of a company. It’s time to go back down market. And so that’s ironically been like usually when that happens is when like ironically like started to go in the market. But the main reason I left and there’s nothing against ricotta. It was amazing experience being there. But like as you see, like AI’s been exponential in the past two years. And it’s when you’re at a large company and it’s no fault of their own. But like they had 1200 sellers over everybody’s. So it’s like, you can’t just go turn on AI, you can’t have 1200 people just going crazy. You’re gonna spend $50 million in token maxing like on accident. Yeah. And so the downfall of that was we had some AI, but like AI at work only matters if it’s like truly connected and everything you do, AI and Stylo is pretty worthless without data. And so as I was meeting with like friends that were going to companies, meeting with VCs and meeting with founders, I was like, I was starting to think about my next move. Like I got hit with this, like deep sense of like an anxiety. And the reason for that was like, I quickly realized, like how quickly AI was developing and how like all these people were using it in their day to day at these early stage companies. And like, I was really concerned that I personally like, was not developing the skills I needed to become employable. It’s going to be very soon in the future that if you don’t know how to use AI that’s completely interactive, how to build workflows, how to like, really run from an AI native standpoint, from the ground up. You’re going to be left behind. Like if you come in as a sales leader two years from now and you’ve been at a company like that didn’t have it, you’re going to be effectively unemployable. And so I had the sense of like, the market’s hot. It’s the right time, it’s the right place. And also like, I was deeply concerned about the skills I was developing. And that even goes for for reps that I talked to and I recruit. It’s like, hey, like do you feel like you’re developing the skills that matter? And the answer is often no. And so that’s part of the pitch is like when you come to someone like campfire, it’s built from the ground up with AI in mind, your ability to kind of like learn and develop, especially those skills like it’s exponential.

18:27 – 18:41

Sophie Buonassisi: Chris, you built sales organizations, pre AI and campfires. Very much so. AI native. You’re building it from near scratch. What’s the difference now of building an AI native sales organization compared to how you might have built in the past?

18:41 – 20:59

Chris McDonough: Yeah, I think one of the biggest benefits is like because we’re building not from scratch. But like I would say, we’re at one. Is that like we don’t have like, the technical debt that a lot of companies have in terms of like our, our CRM, our stack, our tooling. And so it’s when you’re selecting all your tooling for the sales reps, you really think through, like how do these things talk to each other? What’s the quality of the MCP when we’re testing a tool and the MCP doesn’t work well and you can’t actually pull like meaningful data out. Most of these tools are going to become headless to some capacity. So it’s like you’re really thinking through like what are the workflows? How does everything interact with each other? How does it integrate? How do you build workflows across all these tools and how you make those things work? And so like I for instance, like one thing I have is like instead of at clarity at previous organizations and, and I’m gong and, and and all that stuff. I deal insights and so like I’ve built this automation that effectively listens to every call and enriches the deal with Clay Rogers through the CRM and then grades it against every closed, won and lost deal we’ve ever had. And so then I have a daily top deal dashboard that’s fully integrated, that listens, knows every reason why we win lose tied into our battle cards. Also like it uses clay enrichment to tell me when someone leaves the company, when there’s a new hire, if like there’s a new VP coming in that could, like, impact the deal. So just like all those little things, like how do those tools interact, do they interact well and how do they make the team more efficient so you can spend more time on revenue generating activities? I think one of the biggest time savers is top deal reviews. It’s like the wrap has to get a deck. They fill out the deck. It’s do they have med pick? Do they have all these things or is it me or the manager. And we’re listening to the call and like, are we doing this thing? Well now I just have it. And so there’s no slide. I have all the information, every call has been listened to and I have full pick listed out. Is there a next step? Is there a compelling event. And so now it’s like you can stay on top of deals and coach people through deals substantially faster and also like spend two hours building a top deal QBR. It’s not a good use of time. Yeah. And so it’s just it’s small things like that to just save so much time for people.

20:59 – 21:02

Sophie Buonassisi: Oh yeah. Absolutely. And the things that people don’t enjoy doing too.

21:02 – 21:05

Chris McDonough: Exactly. No one wants to build a deck. No, people don’t want to do that.

21:05 – 21:14

Sophie Buonassisi: No. That’s fantastic I love it. And we’ve been talking about campfire, but I think most people are familiar because it is so hot right now. But for anyone who may be unfamiliar, give us a 1 to 2 liner.

21:14 – 23:24

Chris McDonough: Campfire is an AI native ERP. We’re tackling one of the most legacy markets on the planet, effectively going up against the net roots of the world. I think the thing for campfire that I think makes this a very interesting opportunity is ERP is one of the last software modes in my eyes, because ERP is a existential system of record for finance and accounting. Every company on the planet has money. They count the money they have to do accounting. They have to close books. So the Tam is arguably one of the largest. There are because it’s effectively every company. But from there, like the thing that really matters is like Europe cannot be wrong. It is the financial backbone of your operations as well as like that’s how you get audited when you go public. Obviously, for larger companies like, um, there was a I’m not going to say my name was CFO like four months ago that got fired because the ERP put out bad data in the board size were up about 5%. You can’t go to the street with bad data, so it’s not allowed. And so like no one’s going to vibe coat it. You can’t. It’s too complex. It’s and I think the finance and accounting teams are like traditionally like more risk averse. And so like I think there’s a true moat there in terms of software. And then like I think on top of that, like when you have the agenda layer and for, you know, folks that work with the CRM, if you have an MCP or you’re building AI on top of Salesforce, like the data is bad, it’s not good data. It’s a lot of times with humans, even if you have call recording like it’s CRMs are very reliable data sources, and so the AI like is pretty worthless because the data is so bad. ERP is the opposite. Data is right. It’s correct, it’s audited. I’m sure your company. So like your ability to build AI workflows and actually like break into labor replacement long term will be very possible because the data is inherently correct. And so it’ll be a little bit longer to get that going because like you have to build trust that the data is going to be correct as you kind of start building those things. But there is very inherently AI is only as good as the data, and your data on your ERP is like should be correct. And so I think that’s what makes this opportunity so interesting.

23:24 – 23:27

Sophie Buonassisi: Hmm. Super interesting. That’s a good pitch to for.

23:28 – 23:29

Chris McDonough: For example, I want to join.

23:29 – 23:54

Sophie Buonassisi: Yeah I know now I’m excited. I was always excited. It’s been phenomenal to see your journey at campfire. That’s incredible. And I mean, prior to campfire, you spent so much of your career selling to what we often term as the real economy, if you will, which is more of, you know, the logistics side, health care, trucking. We talked about government. How does this relate now to campfire and your strategy?

23:54 – 25:05

Chris McDonough: Yeah. And I think my other point is, like every single industry in the country, around the planet like needs an ERP. They do accounting, finance. And so it’s really about how do you break into those markets. Because the great thing about campfire is we’re in SF and we’ve built a tremendous business through tech and AI. We have some like the hottest logos. And with that then it’s like, okay, the world tech is roughly 35 to 40,000 companies that that matter, right? So if you if you want to become a large, valuable public company, you need to go beyond that. And so it’s like a lot of the strategy is like, how do you break in the middle of the country? How do you sell to that real economy? How do you start tackling those businesses? And because, like, it also makes you be a recession proof business because that was the beauty of like samsara and ricotta during like Covid was like they had such a diversified customer base. A couple of them got killed during Covid shutdowns, but some of them trucking as an example for samsara, went through the roof. Everyone worked from home. You had to get more deliveries, more online. More goods. People were getting stuff delivered to the house. So the trucking industry exploded during that time. And so it’s like, how do you build a diversified Tam and diversified revenue stream that also helps you like fight against economic headwinds in the future?

25:06 – 25:08

Sophie Buonassisi: Trucking industry has been good to you in your career.

25:08 – 25:10

Chris McDonough: Yeah I can’t complain.

25:10 – 25:25

Sophie Buonassisi: Yeah. And so is that part of the plan then at campfire to really diversify your Tam and go beyond. Yeah. At campfire you’ve got some of the hottest AI logos like you said when or perhaps you already are. Do you diversify to the real economy and expand that town?

25:25 – 25:58

Chris McDonough: Yeah, I think like at any given moment, every company starts to expand the Tam. Right? Like, no one’s like, man, I really just don’t want more Tam. Uh, we just have a joke of ricotta that every time they said, uh, Tam in an all hands, um, you’d have to take a shot. We never actually did. But the joke is like you’d be passed out in the first six minutes. So Tam is like, such a big topic everywhere. Um, but yeah, no, it’s something we’re focused on now. It’s like, how do we expand? How do we go into different states, different markets, different verticals? We just recently opened up an office in the UK. We have an office now in London. We now have five heads there. So it’s something that we’re actively looking into and working on.

25:58 – 26:12

Sophie Buonassisi: Brilliant. And because you’ve sold into it in the past and you’re actively working on it now, you have this unique viewpoint into the real economy. Like what do people who don’t have the experience selling into the real economy will want to expand their. What do they get wrong.

26:12 – 28:05

Chris McDonough: Yeah, it’s funny because it was even something like I think samsara got wrong in the very early days, like when you’re in SF and you start a tech, it’s all like, who’s the VC? Which hot company do you have? Like, oh, do you have that new hot logo? Did like the hot VC like give you funding? Um, those people don’t care. They don’t know who XL or Andreessen are. They don’t know what like a round of funding means. They don’t. They don’t know what, like a cursor or like a post tag is they don’t know campfires yet because we haven’t we haven’t called them. And so when it comes down to is like you actually need to pitch actually on the value of the product. It’s very in person. You need to travel, you need to get there. Like my ring jokes. I’ve been to more cities in Pennsylvania that you’ve never heard of. When I was at Simpsons going into Scranton, Pennsylvania, the airport has an office store themed after the airport. That’s how like niche it is. Um, but, um, but yeah, it’s very impersonal. It’s very personal. And it’s funny, they don’t care about the hot logo, but the one thing that gets real interesting when you start, like reaching those verticals is like, you’ll like, be in Texas and like, it’ll be sound like an oil and gas company, and you have like an old gas logo, maybe in Canada. And they’re like, I want to talk to a customer in Texas that does oil and gas at you. It’s like, well, you’d actually be the first one. We only have some. We have some in Canada, that same business. And it’s like, no need to be from Texas. I need to hear something. So like the reference is actually like hyper specific, hyper geographic, hyper local. Yeah. And so then it gets a little bit like difficult like how do you build. Because those people in those type of businesses it’s very tight knit. It’s very, very it’s like some of the tech but like more rural. And so it’s like who do you have, who your references, who looks like us. It’s on the product because they’re inherently skeptical of tech companies out of SF because it’s so different. Like I said, if it’s like it’s own, um, own world at times and it’s very different than the rest of the country, right?

28:05 – 28:26

Sophie Buonassisi: That completely makes sense. Good advice. Lots of traveling for sure. And switching gears a little bit, Chris, but thank you about more high level news. What’s online? There’s a lot of talk around AI, outbound AI, SDRs. I got to ask you, when you hear that, like, what’s your honest reaction as a salesperson?

28:26 – 30:43

Chris McDonough: Yeah, it’s a very interesting topic. And it’s one actually gets put on my plate pretty often. And my, my LinkedIn is also filled with, with people trying to sell that. That’s going to make people substantially more efficient, but I think AI outbound in its current state, if you’re running a complex B2B cycle, it’s just not going to work. I think depending how you use them, they effectively kind of become spam tools. So it’s like you could you just quadrupling output, like if you look at the metrics, like the conversions like very, very low, it’s great for inbound. So if you’re selling like downmarket transactional B2C or like low end B2B, like, hey, credit card or the phone 50 bucks a month, I think that works super well. But I think like the companies that are going to stand out over the next couple of years are going to be the ones that actually, like, truly develop a strong SDR work. Um, and that’s something I learned in my time at samsara, my time at furcata, because like one thing you look at, if you’re looking for samsara, you look at that if you were to go pull up a chart, there’s people that were stars five years ago, they’re still there. They’re in customer success, they’re renewals, they’re enterprise. They’re they’re this, they’re that. And the same thing with ricotta. They did that exceedingly well. I think those are two things that like, really stood out about those companies. And so my opinion of that, especially like for what we’re building campfires, is like, how do you build a really strong SDR org then not just builds meaningful, efficient pipeline for your sales team, but that becomes your bench. Ideally, like I hope five years from now I hire an SDR that I then promote to a director. Like that’s my ideal state because like if you really think about like, how do you build a great company, it’s how do you hire, develop and retain top talent? And it’s much, much easier. Typically internal promotes also like they ramp faster. They have higher code attainment. They’re less risky. And so that’s my hard core belief. That’s also contrarian to AI tools for outbound. Because if you’re doing that and then you have a bench, you’re not developing people. You’re not promoting people. And the SDR org also, it’s like it’s so important because it’s also a place where people learn if they want to become an A. Yeah, and that’s fine if you don’t if you’re a good, smart, intelligent person, we’d like to retain you. And let’s figure out another place to put you. And so then it becomes just like the theater organization for the company at large, and it helps you grow and scale much faster.

30:43 – 30:49

Sophie Buonassisi: It sounds like your largest top of funnel bench that even feeds the entire or perhaps even beyond the sales.

30:49 – 31:46

Chris McDonough: Sometimes it’s existential to recruiting long term. It’s very time consuming and expensive to hire externally all day long. A lot of time doing it, starting new offices. And so once you get that bench, it just makes everyone’s lives easier. And then it just builds a really strong culture. Yeah. Because then like when I’m interviewing people, the main question I get is like, what’s my path? What’s my path to promotion? Like, how am I going to grow my career here? And obviously we’re very new. And so we have promoted a lot of people yet because we just hasn’t been enough time for like five years in. I think nine of the 12 directors were A’s at one point. And so that pitch becomes very meaningful if you you gotta put your money, your mouth, that you promote people internally, show 15 people you’ve promoted. It’s on their LinkedIn. Yeah. So it’s, uh, it’s hard to hide from that. And so I think that’s what really matters for recruiting tool as well, to show that you’re promoting that talent. And it makes people feel like this is a place where I can grow my career.

31:46 – 31:56

Sophie Buonassisi: That almost feels like a good metric for leadership to engaging in. Like, are there any sales metrics that you’re obsessing over? Like, what are the key things that you’re tracking in general?

31:56 – 33:35

Chris McDonough: Yeah, I mean, obviously all the normal, you know, KPIs, pipeline, how many meetings we’re booking dials. But like the long term metric that I really care about and outside of obviously revenue and pipeline, like those are the top two. But like what drives into that and not to go back to samsara, but like if you look at samsara during their like 100 mil to a billion run through IPO, you didn’t see a single top rep leave the organization willingly. Um, the average P club rep was five, six, seven years at samsara. And so they did a phenomenal job of retaining, developing and paying their talent and having really good comp plans, really good structures where people can make a lot of money. And so those people didn’t leave. And so like especially in sales, like over time, your top performers, the longer they’re in seat, they become like exceptionally more productive over time. Like a really good sales org, the top 3,040% is covering probably 70 to 80% of the number. And so one thing I’m really focused on long term is like, how do you not just hire, develop and retain top talent, but are we retaining our top talents? Like what? How much regrettable churn. That was a metric we tracked like very fiercely. Ricotta is like, is this churn regrettable because like those people, you have to hire someone new that the ramp they have to train, they lose the knowledge, they become less productive. And so like, I think that had a lot to do with samsara as exponential growth is because they just retain the top 23% of the org for like 6 or 7. And there’s still folks that are still there eight, nine years. And that’s very rare at that time. Like just the the paychecks are really high and really strong culture. So.

33:35 – 33:45

Sophie Buonassisi: Yeah. Yeah. Regrettable turn I love it. I mean, you’re hiring a ton yourself at campfire right now. Tell us, what are you hiring for and why should somebody join or consider joining Kent.

33:45 – 34:58

Chris McDonough: I’m hiring Chris Stack, so we’re not an office company. So I have an office in New York, SF and London. So really scaling up the org, we’re we’re going to roughly 2 to 3 x the GTM org by the year. So we’re hiring Caesars A’s S’s and then leaders for all those departments. So we’re hiring aggressively across the stack really trying to catch catch the demand of this market. And I’ve said this a little bit across interview. But the reason you’re doing campfire, for all the reasons I said, it’s like if you join a company that is in Hypergrowth, that’s how you fundamentally change your life and change your career. Like people live in SF. Uh, to join life changing companies, to chase life changing equity. And so it’s like, this is definitely a place where we have that focus. We have a focus on obviously development, hiring, promoting internally, but also a phenomenal product. We have a great team, a very large diversified market that is ripe for disruption. So joining campfire is you’re like I said, you’re it’s a tough decision for folks because like you now are going into an interview process. Will Claude kill this company? That’s the thing is.

34:58 – 34:58

Sophie Buonassisi: Everyone’s.

34:58 – 35:13

Chris McDonough: Mind is cloud going to come in and build build this thing and it’s going to crash your company? Until I said no, like ERP is a moat. It’s one of the last moats in software. So I think like it’s a great opportunity. I think we’re very safe from disruption and the market’s large.

35:13 – 35:27

Sophie Buonassisi: I love it. I mean that is super compelling for anyone looking to join a really hot kind of growing company. That’s fantastic. All right, Chris, and to finish us off, we’ve got a couple of just quick rapid fire finish the sentence. Questions for you here. So you ready.

35:27 – 35:28

Chris McDonough: Let’s hear.

35:28 – 35:33

Sophie Buonassisi: It. All right. The part about leadership that nobody tells you is.

35:33 – 36:35

Chris McDonough: I think the thing that people don’t realize about being in this type of role with leadership is I every single day, as you like, lead and operate like a sales org, you have to make decisions. And those decisions like typically have like two outcomes. It’s like is it going to benefit the business. And then how does that impact the people. And so the hardest part about the job is like how do you consistently balance. What’s doing best for the company. Well also what’s best for the people. And how do you tell that line? Because like sometimes we’re going to have to make decisions that are best for the business. We’re here to make money at the end of the day. And like we have a number we have to get to. Um, but then you also take care of people and like how decisions you make. How does that impact them? How does that impact their income, impact their day to day? And so I think like one of the hardest things about leadership is the constant day to day prioritization of like what you’re doing, how are you doing and the decisions you make. And then how do those decisions have downstream impacts to the entire org, while also like benefiting and helping the company grow.

36:35 – 36:39

Sophie Buonassisi: The most underrated piece of go to market advice is.

36:39 – 37:40

Chris McDonough: Yeah, I think the most underrated thing, and this is something like I think about often is I think like companies spend a lot of time, you know, Mark Zuckerberg actually had this like big quote about this, about like how to think about your competitors and how to think about, like what you’re doing day to day. And the companies that win obviously need to be know which players are doing how they’re doing it. But like, you just need to focus on execution. It’s the day to day. It’s like, how are you executing and how we execute everyone else? Because at the end of the day, like you’re one of the main modes of the company is like, how do you go to market? How do you execute day to day? Like what’s your overall strategy? And it’s less about like, what’s a competitor doing? And it’s more so like, what are we doing? What can we do to win, and how do we execute on our vision and really focusing hard on that? I think often people get lost in and like what a competitor is doing or how they’re doing it, or. Like this feature or this function, and it’s like you just got to focus on the day to day and like, how are you executing?

37:40 – 38:01

Sophie Buonassisi: I love it, and I think that’s part of the beautiful part of joining a hypergrowth early stage company is you are just thrust into execution mode. Like there’s no room to not execute. And so you learn to be a fast executor and then you can adapt that to any pace. But like you’re really not given a choice in a hypergrowth environment, like you were taking 70 demos a week.

38:01 – 38:49

Chris McDonough: Yeah. Yeah. I mean, look, I think what happens most is like people get paralysis on decisions in data and like, how do we do that? And I think like Jeff Bezos had a quote about like, is a door a one way door or two way door. And like, you should be trying to make decisions once you have 70 to 80% of the data, because you’re never going to have 100%. And so it’s like when we’re thinking about execution, we’re thinking about the decisions we’re making. It’s like, how quickly can you walk something back? And if it’s two way door and like, I can walk it back pretty quick. It’s like, let’s move first. Like it’s a one way door. And it would take a long time to unwind. Like, let’s be very, very thoughtful. So it’s like something I’m constantly juggling with me and my team. It’s like, how are we making the decisions we need to quickly, and then how do we slow down and think more in depth about like the bigger, harder to walk back decisions?

38:49 – 39:00

Sophie Buonassisi: Brilliant. And just overall it can be go to market. It can be not. But. Chris, what is the best piece of advice you’ve ever been given and who gave it to you?

39:00 – 40:11

Chris McDonough: You know, there’s been a lot of great advice that I’ve received over the years. I think it comes down to like, you can only control two things. You need to focus on control, but it’s kind of similar to everything on execution. It’s like, how do you show up every day? How do you work excruciatingly hard? And like, how do you have a really just good attitude? Because like working in sales and sales leadership, you’re effectively signing up the glass every day. You’re waking up in the morning. You’re calling people. They don’t want to talk to you or they do. You win deals. You lose deals. It’s a very hard job. And so you’re waking up. You’re signing up to do something excruciatingly hard and signing up effectively. Be rejected multiple times a day. And so it’s like you can’t control that. And the best sellers that I’ve ever had are folks that are just laser focused on, like, how do I work hard? How do I control what I can control, and what do I have a good attitude about? Because like, that’s what drives culture. And if you start having people like on the floor or in the organization or even like leaders that don’t have a good attitude or like they’re being negative, like that becomes a drain on the organization. So that’s something that like I’ve held with.

40:13 – 40:19

Sophie Buonassisi: Fantastic advice. And for anyone who wants to get in touch or just keep up with your journey and campfire, where can they find you?

40:19 – 40:21

Chris McDonough: Yeah, you can find me on LinkedIn.

40:21 – 40:26

Sophie Buonassisi: There we go on LinkedIn. And then for anyone interested in Campfire Jobs career page.

40:26 – 40:47

Chris McDonough: Yeah, our career page, or DM me directly. I either respond to every DM I get, or I get the information I send over the recruiter. I’ve hired multiple people already that DM me on LinkedIn. So if you’re looking to be in sales in New York, SF, London, especially if you have a strong finance background like I love the chat, we’re tripling the org. So we need a lot of great people.

40:47 – 40:51

Sophie Buonassisi: And Chris, I gotta ask you, what makes for a good DM when somebody is looking for a role?

40:51 – 41:39

Chris McDonough: Yeah, I mean it’s not just a good DM. You know, it’s funny, if you’re a sales person, you very likely have access to tools like zoom and phone Clay. And so I’ve actually had people pull my cell phone information and contact me. I think that’s phenomenal. I’m putting that person in process if you’re like looking for an SDR role and you cold call me and text me, try to get a job, my company like I very likely want to hire you. So like DMs are good and not everyone has access to like call data and stuff like that. But like if you’re in a company you like very likely can do that. And so some of the best folks have done that. And I think that’s the best way to stand out. As long as you’re like, do it the right way. But if I have someone who texts me like, hey, Chris, I’m looking for an SDR role. Super hungry. Grabbed your number from zoom info. Mike. This guy can prospect. Yeah. So like.

41:39 – 41:40

Sophie Buonassisi: Demonstrating.

41:40 – 41:42

Chris McDonough: Instantly bringing him into the funnel or her.

41:42 – 41:51

Sophie Buonassisi: I love it, I love it, and I think even if somebody maybe doesn’t have access to that and they’re just sending a DM, there’s so many different ways to stand out. Like a video, for example, I just write text.

41:51 – 41:51

Chris McDonough: Exactly.

41:51 – 41:53

Sophie Buonassisi: Make a video of yourself. Yeah.

41:53 – 42:13

Chris McDonough: It’s also like you got to follow up a little bit. Yeah. You know, because like, it’s funny, as someone who tells my team to outbound, you know, whenever we have news or anything, we, we all get like probably 45 LinkedIn DMs a day of people trying to sell us stuff. So then it’s like, sometimes I just miss it. And so it’s like also like it’s the follow up which also ties in sales. Like you got to follow up.

42:13 – 42:15

Sophie Buonassisi: Yeah. Demonstrate the role before you’re in seat.

42:15 – 42:16

Chris McDonough: Absolutely.

42:16 – 42:21

Sophie Buonassisi: I love it. Well Chris, thank you so much. This has been phenomenal. Really appreciate you coming on GTM now.

42:21 – 42:22

Chris McDonough: Thanks for having me.