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Harry Stebbings
Founder of 20VC Fund, 20VC

How to Build a Sales Machine | Max Freeman, Ramp

📅 Oct 10, 2026 20VC with Harry Stebbings 72 MIN 8912 VIEWS 219 SEGMENTS · 2 SPEAKERS
Max Freeman is SVP of Sales at Ramp. He joined the company as its first sales hire. By 2025, he was leading more than 300 salespeople, helping build Ramp's sales organisation from the ground up. ----------------------------------------------- Timestamps: 00:00 Intro 01:08 Why Ramp Hires Investment Bankers Into Sales 06:39 How to Hire Great Salespeople 09:09 How to Tell a Great Seller From an Order Taker 12:49 What Salespeople Should Look for When Joining a Startup 17:14 Why Sales Is Really an Engineering Problem 23:15 When Should You Verticalize Your Sales Team? 24:35 How to Compress Enterp...

What Harry Stebbings said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Max Freeman, SVP of sales at Ramp, discussed building a sales machine, emphasizing hiring 'mispriced assets' like investment bankers who are programmed to work and can cold-call CFOs credibly. He advocates paying 2x market rate for SDRs expecting 4-6x output, and hiring from companies with low NPS but significant revenue growth. Freeman advises founders to avoid comp plans initially, using 100% OTE for the first two quarters, and to hire sellers in pairs. He detailed Ramp's onboarding boot camp (60-90 days), with certifications required before reps get accounts, and stressed the importance of leaders being hands-on, even making cold calls and sending five cold emails daily. He discussed verticalizing sales teams only after owning 3-5% of the market, compressing sales cycles through rigorous qualification, and using internal tools like Ramp Revenue and Inspect to automate outbound and pre-call research. Freeman believes customer success is an economic engine driving NDR, and he holds sellers accountable for forecasting accuracy as part of performance reviews.

Key takeaways

  1. Ramp pays SDRs 2x market rate but expects them to book 40-60 meetings monthly, 4-6x the standard.
  2. Freeman advises founders to use 100% OTE comp for the first two quarters and hire sellers in pairs, not one at a time.
  3. Ramp's onboarding boot camp lasts 60-90 days; reps must pass disco and demo certifications before getting accounts.
  4. Freeman recommends verticalizing sales teams only after owning 3-5% of the market to lift conversion.
  5. Ramp's internal tools, Ramp Revenue and Inspect, automate pre-call research and enable custom demos, unlocking significant seller capacity.

Numbers and commitments

FigureWhat it refers toTypeAt
2x Pay above market rate for SDRs commitment 4:11
40, 50, 60 meetings Monthly meeting booking expectation for SDRs metric 4:11
4 to 6 times Output expectation vs standard SDR metric 4:11
15 plus calls Daily calls by some Ramp AEs metric 6:08
3 to 5% Market share threshold before verticalizing guidance 55:04
just a hair under 1% Meeting response rate from outbound emails metric 22:40
100% OTE Comp plan for first two quarters guidance 28:36
60 to 90 days Onboarding boot camp duration timeline 39:07
5 cold emails Daily cold emails Freeman sends commitment 1:01:53

Chapters

  1. 0:00Hiring bankers and mispriced assets
  2. 4:11SDR pay and output expectations
  3. 11:32Interview process and business case
  4. 28:36Comp design for early teams
  5. 36:49Onboarding boot camp and certifications
  6. 43:32Quota multiples and ramp times
  7. 47:45Customer success and NDR
  8. 49:58Forecasting and pipeline reviews
  9. 55:04Internal tools and capacity unlock
  10. 59:00Leadership lessons and personal growth

Questions asked in this interview

12
  1. 0:34We'll pay 2x what a standard SDR is going to make. But guess what?
  2. 9:08You want to understand, talk to me about a deal that keeps you up at night, why did you lose it?
  3. 13:15You're doing like AI revenue forecasting?
  4. 15:23And so talent density, if we just unpack that, like is that just how good the team is? What does that actually mean?
  5. 20:01You might have three to a half a dozen of folks that are responsible for outbounding. Guess what?
  6. 23:15But as you own more and more of the market, I think this is arbitrary, but I'd say, you know, three to 5%, guess what?
  7. 27:10Are you trying to make your accounting function more efficient and give yourself FTE leverage?
  8. 31:12Like if someone isn't performing well?
  9. 40:49You're going to be in team meetings, listening to pipeline reviews and forecasting calls and everything in between. And then guess what?
  10. 48:40We have to think through how can we thoughtfully cross-sell, upsell, and expand all with the goal in mind of driving financial impact and operational efficiency for our customers. But guess what?
  11. 55:04You have to go perform your independent research. What does that mean?
  12. 1:02:41If I'm not buttoned up in executive conversations with Eric, whether it's external with a customer or internal with a hot board topic, why would I still have this position?
Harry Stebbings 0:00 ↗
There's three categories of performance in sales. One, you are God. Two, I don't know yet. Or three, you're getting fired. Today, we're joined by one of the fastest growing companies in the world's SVP of sales, Max Freeman, to understand how to think about onboarding, how to think about acquiring the best talent. By the way, he thinks bankers make the best sales leaders. How to think about retention, how to think about incentivizing sales reps with new products. All of this and so much more in what is one of the most granular and detailed shows on how to build a sales machine.
Max Freeman 0:34 ↗
We'll pay 2x what a standard SDR is going to make. But guess what? You got to book 40, 50, 60 meetings, which is four to six times what a standard SDR has to book. There are some sellers at RAMP that are on 15 plus calls in a given day. You have to treat go to market recruiting like Billy Bean. Sales is very much an engineering problem when you break it down. It's a data infrastructure problem. It's a math problem. Ready to go.
Harry Stebbings 1:08 ↗
Max, I am so excited for this, dude. I think when people think of the fastest growing companies, they do immediately think of RAMP. And so, Eric told me that the entire revenue accumulation was down to you. And so, no pressure, but the next hour is going to be a lot of treasure trove of wisdom. Okay.
Max Freeman 1:29 ↗
I love it. I'm fired up. And I think I'm getting too much credit for that. There's amazing individuals on the go to market team at RAMP. And I feel very lucky.
Harry Stebbings 1:38 ↗
Well, it's great because I was totally BSing. He said you're a total douche. But, moving swiftly to the show. A sales team is nothing without the people in it. And when we were chatting before this, we don't do prep calls. No, Harry's far too old and arrogant for a prep call, but you made me do a prep call and I'm so glad you did because you said that you like hiring bankers and turning them into sellers.
Max Freeman 2:04 ↗
Yes.
Harry Stebbings 2:04 ↗
Why?
Max Freeman 2:05 ↗
So not only bankers, but I think there's a lot of mispriced assets on the market where their resume will not suggest the true alpha. But let's start with bankers. So in building the early go-to-market team at RAMP, we brought on quite a few investment bankers and now they're running pretty large pieces of the business. Here's why I have an affinity towards doing this. One, bankers are programmed to work. The concept of a nine-to-five is completely foreign to these folks. Two, they have intelligence and they have business acumen and a lot of horsepower that is not always found when hiring for sales talent. And I think the third for our business, you know, we're selling into the office of the CFO. And so in the earlier stages when we didn't have brand recognition, no one knew who we were as a company, being able to call a CFO cold, tell them, hey, I just quit my job at Goldman TMT to join this credit card business. That packed a very compelling punch for us. And so I think those were the tangible benefits. Maybe the last additive component that I think is important is I didn't have time in early sales teams don't have time to teach folks this is how you use lean language in a cold call. This is how you use appropriate grammar in a cold email. We had to be executing and so bringing on folks like that helped derisk a lot of that. So we were just in pure execution mode. And now today, you know, Mike Weber, we pulled him from Citi. He runs a massive piece of the business. Sam Buck runs a massive piece of the business because he came from Goldman.
Harry Stebbings 3:53 ↗
I spoke to Sam before this show, who was fantastic with suggestions. My question to you is, I can literally feel the pain of founders listening going, really, how on earth do you afford these investment bankers? How do you afford these investment bankers?
Max Freeman 4:11 ↗
Yeah. So the bet we took early on was to actually pay way above market rate for this talent. But in return, we were going to expect way above market rate when it comes to output. And so we'll make the unit economics work. We'll pay 2x what a standard SDR is going to make. But guess what? You got to book 40, 50, 60 meetings, which is four to six times what a standard SDR has to book.
Harry Stebbings 4:37 ↗
You book 40 to 50 meetings. What is the expectation on meeting bookings? Really?
Max Freeman 4:42 ↗
It depends by segment. Obviously, the further up market you go, the numbers are lower and we're looking for quality, but down market we still have SDRs that are booking well above 50 meetings in a given month.
Harry Stebbings 4:56 ↗
That's not very much, dude. 50 meetings in a given month for an SDR.
Max Freeman 5:01 ↗
You have to book a meeting with intent. There has to be qualification rigor. There's a lot that goes into it that takes precision. I think you're understating this.
Harry Stebbings 5:15 ↗
But when I No, because when we were chatting before, I said like DGEN Chris Denon is like, oh, you can't do more than seven. And you were like, oh, people do way more than that. They do like 10 in a day.
Max Freeman 5:25 ↗
Those are those are account executives that are taking seven actual meetings like the closers.
Harry Stebbings 5:32 ↗
Ah,
Max Freeman 5:33 ↗
not the top of funnel that's like booking.
Harry Stebbings 5:36 ↗
Booking the meetings for the sellers to then take. Do you not expect even like the low ACVs to be doing way more than 12? These are small businesses like startups. Like
Max Freeman 5:46 ↗
I'm talking about SDRs specifically on the AE side. Yes, of course. They're taking more than 12 meetings in a given week especially down market with the low ACVs. Our inside sales reps, our commercial reps, they're taking 10 to 12 calls in a given day.
Harry Stebbings 6:02 ↗
That's what I'm talking about. Yes.
Max Freeman 6:03 ↗
Okay. Sorry. So that that that was the disconnect. So there are people doing 10 times 12 calls a day.
Harry Stebbings 6:08 ↗
Absolutely. There are some sellers at RAMP that are on 15 plus calls in a given day.
Max Freeman 6:13 ↗
Okay. That's what I'm talking about. Okay. Yeah.
Harry Stebbings 6:15 ↗
Right. And and sorry they are AEs or SDRs?
Max Freeman 6:18 ↗
Account executives. AEs.
Harry Stebbings 6:20 ↗
They're doing like 8 to 10 a day. Got you. Great. There is another component though to teams which is we can't just have IB. They got to come from some tech company. There are tech companies where it's good to hire from versus bad to hire from. And I'm not asking for explicit names, but like profiles for me as a founder to think through.
Max Freeman 6:39 ↗
Yes, I love this. I obsess over this topic. So I am a huge fan of Moneyball and you have to treat go to market recruiting like Billy Bean. And so there is so much alpha in finding what companies have grown revenue in a significant way. I'm talking north of nine figures, but have done that despite having a low NPS score. Now, why is there so much alpha in this? A few things. You have to create a lot of your own demand. If you're the fifth or sixth best player in your market, the inbound funnel, that's not very fruitful. So, you got to go make it happen. Two, you have to navigate a lot of complexity in your cycles. One, there's probably a lot of weak reviews on third party publications, whether that's G2, Capterra. So, you got to be dialed in to advance opportunities. And three, you're usually priced at a premium compared to other players in the market that are priced significantly below you. So, if you can be the number one or two seller there, you come into a system like RAMP, that is where the magic is going to happen. If you were to name a company,
Harry Stebbings 8:00 ↗
I can't give away the secret sauce. I'll name one. I'll name one. Sixth Sense.
Max Freeman 8:06 ↗
Former low NPS products. Maybe not great.
Harry Stebbings 8:10 ↗
Correct.
Max Freeman 8:11 ↗
But close good customers.
Harry Stebbings 8:14 ↗
Exactly. In fact, just yesterday, one of our top enterprise sellers sent me an email from a customer that said this huge review that they sent internally. They want to offer a case study and we didn't even prompt them at all. And Alex had said, I've never seen this in my 15 years of sales. I was like, oh, we get that 10 to 20 times a month at RAMP. You've just been selling [__] products.
When you're trying to determine greatness in a candidate in terms of where they've come from before. How do you unpick whether it was truly them or whether they were just an order taker? You can have two different situations. One, they're just an order taker, which isn't very difficult. Or two, they're at Twilio and they sign up Uber and they sign Uber when it starts and then it expands into what it becomes and they get the credit for that. How do you determine true quality versus happenstance or order taking?
Max Freeman 9:08 ↗
Yeah, you have to decompose their number, right? And so, okay, you did 2 million, that's great. How much of it was inbound? How much of it was outbound? How much of it was expansion? How much of it was sourced by your founder? How much of it was from existing opportunities that you inherited? And then you really have to drill down such that you can spot and figure out if someone is bullshitting you. And then to get even more deep into testing their acumen around sales, it's talk to me about two deals. You have to make them reconstruct them chronologically. The best candidates give so much texture and like you're really trying to figure out well how did you advance this? Well, what was it? Were you articulating business value? Was it some workflow that you tied to a business outcome? They'll know that. And if they can't describe that, not a good sign. The inverse is also true. You want to understand, talk to me about a deal that keeps you up at night, why did you lose it?
Harry Stebbings 10:09 ↗
If they can't unpack why they've lost an opportunity, was it they were single-threaded? They didn't build a champion? There was no business value? The product wasn't good enough, they didn't qualify well enough. Like figuring that out and testing for it is actually incredibly important in an interview process. What if I said to you, hey, yeah, I get you. One of the decision makers is friends with a competitor and that's why like I kind of hate it, but I also get it. Like blame deflection can also be genuine. How do you determine like good versus bad on that sort of thing?
Max Freeman 10:46 ↗
Totally. You should be able to sus that out early enough in the cycle and you should confront it head on. Hey Harry, I know you're evaluating us and another competitor. I see you have a shared board member with that competitor. Is that going to get in the way of this decision? Like how are you actually evaluating it? Is it on its merits or is it not? A seller should be able to articulate and communicate that to me. They shouldn't find out about that at the final second after they've rallied all of these internal resources to take a deal through a cycle.
Harry Stebbings 11:19 ↗
Okay. So, I've done pretty well in this set of questions. I'm running through this hypothetical interview process with you. Next step, do I need to do a demo? Do I need to do some form of case study with you? What happens next in our process?
Max Freeman 11:32 ↗
Yeah. So you definitely have to do what we call a business case which is assuming the role of a seller at RAMP and you have to go through a discovery call. We'll give a prompt in advance and we really test for three things. Those three things are RAMP as a business and as a product, the prospective company in question, like are you doing your research? Do you know what's going on? Have you read their 10K? Things of that sort. And then the third is just selling fundamentals. Do they have executive presence? Can they get second and third level discovery questions? Can they quantify pain? Can they articulate the value? And then more than anything, not to oversimplify, would I buy a product from this person? If I can't say that with conviction, I'm not going to hire them. I feel the same way about hiring leaders. If I'm trying to hire a leader and I don't think I would work for that person, I wouldn't make the call.
Harry Stebbings 12:32 ↗
And so you sit down with me and you realize that you would buy from me and you do want to work with me. What does the offer stage look like? What do you look for in how I respond to equity versus title versus comp? What then?
Max Freeman 12:49 ↗
I have so many thoughts on this. It so depends on where you are in your career. If you're a seller looking to join an early stage company, thinking about equity, cash, and comp is actually the wrong thing to index on. The right thing to index on is the market, the talent density, the business, and the founders. That's how you have to underwrite it.
Harry Stebbings 13:13 ↗
Why the market?
Max Freeman 13:15 ↗
Because there's structural advantages if you pick a business that can continue to find growth vectors. Right? My RAMP story. The reason why I left, I was a mid-market account executive. I quit my job to become an SDR all over again at RAMP. And people looked at me like I had 20 heads. The reason why I did it though is the market had unfair structural advantages. The card business, it's a trillion dollar plus a year market. Expense, same thing. Bill payments, multi-trillion dollar a year market. Travel, multi-trillion dollar a year market. Banking, multi-trillion dollar a year market. So you don't even have to be a good business to find a way to grow just given those dynamics. The fact that you have the market leading product, you have the most talent dense engineering roster that looks more akin to that of a lab, that of a SpaceX, you're going to win. And so because of that, that's where you get the career acceleration. Like if you care about, oh, I want the VP title and I want a ton of equity, but you're going to go work at a mediocre business that might grow 20, 30% a year. Who cares? You're making the wrong trade. So, with the greatest of respect, for people that go and work at like AI sales tools, I'm like, really? You're doing like AI revenue forecasting? I'm not being a dick, but I'm just being honest. I'm like, that's really
Harry Stebbings 14:48 ↗
I feel the same way because exactly. Yes, that's exactly my point.
Max Freeman 14:52 ↗
Yeah, it's like the John Sculley, you know, the Apple moment. You're really gonna spend the rest of your life selling flavored water.
Harry Stebbings 14:59 ↗
That's it. Unless you have the belief and the conviction that this could turn into something that rivals Salesforce, sure, by all means. Go swing for the fences. But that's hard.
Max Freeman 15:12 ↗
Totally get you. So, sorry. Number one was market. What was number two and number three? Talent density.
Harry Stebbings 15:17 ↗
Talent density on the current roster.
Max Freeman 15:20 ↗
Yeah.
Harry Stebbings 15:21 ↗
And then third, founders.
Max Freeman 15:23 ↗
Okay. And so talent density, if we just unpack that, like is that just how good the team is? What does that actually mean? You know, working in sales, you want to be the beneficiary of having killer engineers. And so first engineers that I met at RAMP were otherworldly. It was like the youngest person to ever graduate from MIT, someone that had already built and sold a business to Apple in his dorm room at Stanford. You know, the II gold medal Olympic track, that is that that's what you want to underwrite. And then the fact that Eric and Kareem had already built and sold a business to Capital One, that doesn't happen by accident.
Harry Stebbings 16:00 ↗
That's a pretty solid engineering team to start with, isn't it? Youngest kid to ever graduate from MIT. Gosh. God. Okay, fine. My four weeks at university are really making me feel guilty now. That's why we're sellers, Max. Okay,
Max Freeman 16:17 ↗
That's right. That's right. I went to state school, baby.
Harry Stebbings 16:20 ↗
Yeah, there we go. Okay, so that's talent density. I get that. And then the third is founders. And when we say founders, like can we unpack that a little bit because we see a rise of engineering founders who suck at sales, definitely haven't built out a sales playbook, definitely don't have really much clue about sales. How would you think about that as a potential founding team to join?
Max Freeman 16:41 ↗
That's totally fine. And I think we're going to see more and more of that. As a lot of engineers who are looking to go start their own AI native businesses, I think you need to test for a few things. Are they seller friendly? And I'll explain an example of what that might mean. And then two, their willingness to engage and be involved in taking feedback such that the product can mature and become sophisticated enough to meet the demanding needs that sales will face. But I'll go deep on the first example. Being seller friendly. What does that mean? Well, will your technical co-founder give you engineering resources to help build the machine? Sales is very much an engineering problem when you break it down. It's a data infrastructure problem. It's a math problem. And so, you need to build the systems to help give you leverage and automate such that you can create a ton of capacity. And I think I give a lot of credit to Kareem early on with providing engineering resources to myself to build out our OATS program super early on in the business.
Harry Stebbings 17:53 ↗
I'm so sorry. What is an OATS program? Why is it a data infrastructure problem? Why is it a math problem? Can you just help me understand this? Seriously?
Max Freeman 18:02 ↗
Yeah. So outbound used to primarily be a writing and a calling problem. I think increasingly it's becoming an engineering problem. In late 2020, early 21, even before the rise of AI, we built our own internal infrastructure to help automate a lot of our outbound. And that's what OATS is an acronym for, outbound automation team. And so let me break this down. So the team was understanding what I was doing to go to market. How I was creating signals inside of accounts. And the signals could be unbounded. It could be a new hire just joined the business. It could be I went to the same university as this person. We have overlapping investors on our cap table and that was very manual. You know, you got to build the templates, you got to find the contact data. Well, why is our sales team doing that? They should be focused on just speaking with the customer and helping solve their business problems and getting RAMP deployed. And so our team of engineers built a lot of automation to do the list scraping, do the email outreach, and it was
Harry Stebbings 19:23 ↗
I'm so sorry. So if I'm a founder then listening to this wanting to do the same, what do I do? I tell my engineers to get ZoomInfo.
Max Freeman 19:32 ↗
No, that's part of it. You tell one or two of your top engineers that, hey, we could build the coolest product in the world. It doesn't [__] matter if it doesn't get into the hands of paying customers. And so we need to obsess over growth as it's existential for our business.
Harry Stebbings 19:50 ↗
What are we solving for here? I don't get it. Are we solving for finding new leads or for outreach to them? How do we handle the integrations of whether it should be an email or a LinkedIn message?
Max Freeman 20:01 ↗
Yeah. You're solving for coverage, right? In the early innings of your business, you're not going to have an army of go to market talent. You might have three to a half a dozen of folks that are responsible for outbounding. Guess what? That's if you do that manually, like maybe you could get a couple hundred emails out. Maybe you could make a hundred dials. That's not enough. Especially in markets today where the TAMs are becoming more and more unbounded. You need leverage. And so the problem you're solving for is coverage and brand awareness and getting your name out. You just can't be dependent on sellers to do that.
Harry Stebbings 20:44 ↗
Do you not think you have efficacy reduction? In other words, less efficient outbound with scale versus if I sent 20 really, really great messages that are researched, thoughtful, included a joke about our alma mater and a picture of me and my mom walking on the weekend. My efficiency would be through the roof. Genuine asking, not telling.
Max Freeman 21:08 ↗
That is a concern. You have to make the system recursive to actually understand what is yielding results such that it optimizes over time. And so if you're just relying on automated emails that are going out and out and out, that's irrelevant. You have to constantly be A/B testing and pulling in what's actually going to yield the best results. And then guess what? You still allow for manual outreach from your sales team because they, to your point, if you're going to send 20 unbelievably curated notes, the likelihood of those getting responded to, sure, it is higher. And then the system can identify that, take that feedback, pull it in and start actually doing it at scale.
Harry Stebbings 21:49 ↗
Do you have engineers in sales permanently? This isn't like a one-and-done sales tool build.
Max Freeman 21:55 ↗
We do. We have a growth engineering team that, yeah, I think there's at least half a dozen engineers that truly obsess over building products for go to market.
Harry Stebbings 22:07 ↗
What's a good response rate when you're sending outbound in a tool like this?
Max Freeman 22:12 ↗
Response rates over time since the acceleration of AI have actually regressed pretty meaningfully. But response rate isn't the right metric to index on. It's meeting response rate because like you could get a 5% response rate but if they're saying please never email me again or opt out or [__] off, that's not directionally helpful.
Harry Stebbings 22:37 ↗
And so is how many you convert to a meeting.
Max Freeman 22:40 ↗
Yeah. And that should be just a hair under 1%. I think is really, really strong standard. So for every hundred emails you're sending, those convert to one. That's great.
Harry Stebbings 22:53 ↗
How quickly do you verticalize your sales team? Because all of this can become better, more efficient, more accurate with verticalization. Hey, we've got clients including British Airways, Delta, and Ryanair. Oh, wow. Okay, we're targeting the travel industry and specifically airlines. Do you see what I mean? When is the right time? And how do you think about that?
Max Freeman 23:15 ↗
Yeah, I think the right time to verticalize your business is when you need to pull the lever to lift conversion. And so I think companies actually verticalize far too early. Especially if you have a huge addressable market, you're in land grab market share mode. And so I think verticalizing the business may actually be counterproductive to doing that. But as you own more and more of the market, I think this is arbitrary, but I'd say, you know, three to 5%, guess what? The total amount of opportunities you can go after starts to become contained. And so the lever that you need to pull is you need to be able to convert leads to close one at a higher clip. And so I think that is the moment when you start to verticalize. You know, looking at companies that I think have done this moderately well, the Oracles, the Workdays, the SAPs of the world, that's exactly what they've done.
Harry Stebbings 24:14 ↗
One of the reasons I like verticalization of sales teams is what it does to sales cycles. Often the messaging is better. It's more accurate. Value props kind of clearer, and I just see a compression in the sales cycle when I see that verticalization. What are the biggest lessons you have on how to compress sales cycles?
Max Freeman 24:35 ↗
It's nuanced depending on the segment that you're going after. But the best way to compress sales cycles is qualifying with more rigor. So upstream you need to understand does this person have the influence to actually effectuate change? And are they reasonably committed to doing this within a 12-month period? If you could check those boxes, yes, swing at it.
Harry Stebbings 25:01 ↗
How do you determine that actually? Because a lot of people like to have ego and say they're very important and a lot of people will like to please you and say yes, they'll do it fast. How do you actually determine it?
Max Freeman 25:12 ↗
Yeah, you've got to test them. The way to test them is if they're not in the C-suite or they don't have a VP title, you have to know who their boss is in the org chart. And so if you've had an unbelievable call and you've earned the right to pull in another stakeholder, you have to ask for it. And there's a subtle way to do this where it's seemingly a give to get. Hey Harry, today was awesome. I have a lot of conviction that we can solve this problem for your business. We're going to knock this demo out of the park. I'm going to bring on a bunch of my technical resources in an effort to bring them onto the call. My ask would be that you bring Susan, your VP of procurement, into this next conversation. You'll know right then and there. Is this person going to, is Harry going to bring Susan into the call? Okay, great. You may have a champion. You may have someone that can effectuate change. If not, oh, why aren't you? Are you just window shopping? Do you not have a relationship with your boss? Can you not actually do this? So, it's a really good way to test that out.
Harry Stebbings 26:15 ↗
Ah, so I love that and Susan would love to come. One thing that's really important for us right now is just cost controls. And so Max, can you help me out here? You're saying that you're charging, you know, four bucks per card or four bucks per seat or four bucks per unit of whatever we're selling. I'm going to need it at two. Are you going to be able to meet me there, Max? I guess to buy we haven't even determined technically if this is going to fit for your organization.
Max Freeman 26:48 ↗
And so look, we can figure out economics. I think once you see how this product's going to transform and change your business, it's going to be a lot more financial impact back to 20VC than trading two bucks.
Harry Stebbings 27:02 ↗
But so you don't engage on discounting because so many founders say to me, I just don't know how to do it. I want to close the deal, but they want a 20% discount.
Max Freeman 27:10 ↗
Yeah. I think like early on in the conversation, if we're coming to discuss economics and pricing after call one, that's usually a bad sign. It's not a sophisticated buyer on the other end. Unless it's super down market, you're talking to a 10-person startup founder and you're trying to one-call close, like for sure, maybe I'll engage that way and we'll discount to get the deal in the door. But up market, no, you have to co-author business value assessments. Like, you really have to understand what are they trying to solve and what does the total cost of ownership look like? Are you trying to get a margin win? Are you trying to make your accounting function more efficient and give yourself FTE leverage? And if you could mutually agree to that, you could circumvent any pricing concessions because hopefully you're driving seven figures in value creation.
Harry Stebbings 28:12 ↗
Speaking of driving seven figures in value creation, we're going to go back to this like beautiful interview process because I've impressed you so much. You're so excited for me to join RAMP day one and you want to give me a job and it's time for comp design. Okay. Compensation design. Can you help me? How do you advise founders on comp design for the first AE and the first SDR?
Max Freeman 28:36 ↗
Yeah. I usually advise to not have a comp plan. I usually advise to do 100% OTE for at least the first two quarters. You just don't know what you don't know. And I've actually seen founders get into some trouble where they make a quota that gets blown out in the first six months and it's, holy [__], I owe this seller multiple six figures. I've seen the inverse happen as well where you arbitrarily finger in the air. Oh, I think this person could close this amount or I think this person can book this many meetings and it's not attainable and then you're struggling to get momentum and a tailwind going.
Harry Stebbings 29:18 ↗
And then confidence gets hit and confidence is hard to regain once lost, I find.
Max Freeman 29:23 ↗
Correct.
Harry Stebbings 29:24 ↗
Yeah. Even if they do okay, I've seen it though where even when they do okay, I'm making up numbers. Say they close 250 but you set me 500. 250 would have actually been okay. It was solid. Like decent, not a bad start. But because it was half of what you set, I feel like I'm really bad.
Max Freeman 29:41 ↗
That's right. And in some ways, there's a little bit of benefit to that where, you know, if you get the right person, they've got a fire lit under them and they feel like they're not meeting expectations. There's some healthy angst, but it depends on the archetype that you bring in.
Harry Stebbings 29:56 ↗
Well, so just to pause, so we're 100% OTE. When does that change and how do we then instigate a different discussion around correcting that plan?
Max Freeman 30:05 ↗
Data. Like typically this would take, it depends on what segments you're going after, but if you have cycle times that are less than six months, you should have enough data in the system to figure out, okay, this person has been in seat for two months, they've ramped for the first 90 days, we're seeing stage progression here, we have reason to believe that pipeline's going to be X, let's make a quota that is both ambitious and somewhat reasonable based on the data that we have. And you should never hire one seller, one SDR at a time because the problem is how are you going to benchmark their performance? How do you know if they're good? Are you going to benchmark them against yourself as the founder? I don't think that's reasonable. Also as a founder, if you're going to be spending time onboarding a seller, that's laborious, that's expensive. Do it in pairs and there's competition, there's collaboration. They're not lonely. I strongly advise against one at a time.
Harry Stebbings 31:04 ↗
Okay. I totally get that. And so we strongly advise against one at a time. Do we always shed one or do we sometimes keep them both?
Max Freeman 31:12 ↗
How do you mean? Like if someone isn't performing well?
Harry Stebbings 31:15 ↗
By nature of having two, one will always perform worse than the first. How often do you keep them both versus get rid of one?
Max Freeman 31:23 ↗
I think it depends. If someone is just a complete outlier destroying the other seller, yeah, you probably need to shed that person. If it's a 10 to 20% delta, you have to go deeper and unpack it. Like why is this person winning more? Like what structural advantage might they have? Is it pipeline that I gave them? Is it pipeline that came from our cap table? Is it something else? Do they know the product better? Are they more motivated? Do they give a [__] and the other person doesn't? Like this is on the founder to go ascertain.
Harry Stebbings 31:58 ↗
So for the 100% OTE, sorry going back to that, that's for SDRs. Does that change when we're doing comp design for AEs?
Max Freeman 32:06 ↗
No, it's unilateral across early go to market teams. Yeah.
Harry Stebbings 32:10 ↗
What are the big mistakes you think founders make when they're doing comp design? Because again, like we have challenging nuances like when you have new products you want to incentivize them more. You want to encourage bonuses for selling more of those, but I don't want to then have a load of people sell all of that and none of the core. How do you think about that?
Max Freeman 32:30 ↗
Depends on stage first. If you're an early stage founder, you're probably still trying to take one product to market and you want to focus on that. You really need to understand your ICP. Said another way, it's so much more valuable to have 20 customers that are raving and thrilled about one single product offering than you in a half-ass way serving six customers on multiple products that aren't as thrilled. You need to get the tailwind going of case studies, references, and positive momentum across your business. Later stage though, like where RAMP is today, incentive design is incredibly important and I think it's existential to over-incentivize new products to get off the ground. And so thinking through 2x to 3x quota retirement for new products, you got to get the momentum going such that you earn your way into more multi-product customers, more case studies, more momentum.
Harry Stebbings 33:39 ↗
When you get a hire wrong, Max, what do you not see that you should see? So, like for me sometimes I'm quite overtly aggressive. It's very innate. I'm intense and I'm going to [__] kill competition and I'm going to salivate over it and I'm happy to talk about that. The quiet killers I don't find as easy sometimes to uncover. That would be the talent that I miss and I try and correct for that. When you make a mistake on hiring, what do you miss that you should see?
Max Freeman 34:12 ↗
People in sales, especially leadership, naturally tend to interview well. They are sellers by trade. They know how to say the right things. They know how to respond extremely quickly in the interview process to show that they are urgent and can follow up ruthlessly. I think the only mistakes that we've made are over-indexing on pedigree and coming from, you know, the big-name brands and not truly understanding two things. One, do they have the agency and do they possess the figure-it-out X factor where they do not need to be dependent and reliant on so many different internal resources. And then two, which is related, are they going to go all-in? Are they going to have a deep obsession with working at RAMP? Like it has to become their identity. And if both of those things aren't ascertained crisply in the interview process, it could come out and it's sometimes the wrong hire.
Harry Stebbings 35:19 ↗
Chad Peterson said on the show, legendary sales leader, he said that young people just don't want to work. And that there is a different appreciation for work. They want to work from home. They want work-life balance. They want mission. They get burnt out. They want kombucha. Is he right?
Max Freeman 35:42 ↗
I love Chad. So much. He's a beast. I love Peterson,
too. That was a fun show. I think he's right. It's a bit provocative, but there are plenty of young professionals that do want to go all in, and you have to find them. And it's on you to build the culture internally to make sure people want to come into the office every single day. We have younger sellers in their career that badge in on Saturdays and Sundays. Nobody's asking them to do that. But if you create that culture, it's super infectious. And the beauty of that culture is it sniffs out people that do come in that don't want to adhere to that. Like, look, if you want to work remote and you want to make calls for four hours a day, other ICs in the business are just not going to let that permeate throughout our work.
Harry Stebbings 36:38 ↗
Help me understand. I'm delighted to accept your offer. Thank you so much, Max. What have been your biggest lessons on how to onboard new reps effectively?
Max Freeman 36:49 ↗
So early stage, you're all locked into a room. Okay, you're going through four very key components. The first of which is the product and the technology that you're selling. And I'll go through all of these in sequential order. The second is the buyer personas that you're selling into. The third is the competitive landscape, and the fourth is just like the internal operating chaos of how your systems run and what you need to know as a seller. And so on point one, look, in the age of AI, and especially as the next generation of buyers sit in seat, they have what I would describe as [__] repellent. They are direct. They could get answers quickly. And so the expectation is if they're talking to a seller, they need answers quickly, too. And so if you're not technically proficient in your product offering, you're fairly useless as a seller.
The second is the buyer personas that you're selling into. This is really important. You need to know what their priorities are. You need to understand their challenges. And it differs if you're talking to a CFO of a venture-backed software company. That conversation is going to be a hell of a lot different than if you're talking to the senior accountant of a construction business. And you need to know the two. Like, one is going to be super high level. They are trying to drive positive business outcomes. The accountant might need one workflow that is tied to the month-end close that is creating a lot of laborious chaos for them, and you need to have that context-switching capability.
The third, the competitive landscape. We obviously play in an incredibly saturated market. A lot of players claim to do many of the same things. You need to study these businesses. You need to understand their weaknesses, and you need to expose them in a diplomatic way where you're positioning your product to be as perfect as possible for the buyer in question.
Harry Stebbings 38:57 ↗
Do you have a boot camp where you go through these stages?
Max Freeman 39:00 ↗
We do.
Harry Stebbings 39:00 ↗
Can you walk me through that? Like, how long is it? Who leads it? What materials, all that?
Max Freeman 39:07 ↗
Yeah. So, we have a gentleman, Kyle, who runs our enablement business at Ramp. He's fantastic. He's not a traditional enablement leader by any means. He's a killer seller turned sales leader that we've brought in to really perfect not only onboarding but ongoing enablement for our sellers to continue to develop their acumen and product fluency. In the boot camp specifically, depending on the segment, it's going to be 60 to 90 days. The first four weeks is fairly rigorous with many milestones that you need to hit. Some of this is intense hands-on keyboard. Some of it is, you know, self-guided skills that our enablement team has created across all of these different topics.
And then the milestones, there's a lot of rigor that goes into this. You need to complete a disco certification and you need to be excellent. You need to complete a demo certification and you need to be excellent. I like to pop into these periodically, and if you don't complete them, you don't get turned on in the router. You don't get your accounts, and so it's existential that you perform well, otherwise your ability to ramp and become a successful seller is contained.
Harry Stebbings 40:33 ↗
How long before I start speaking to clients or customers on my own?

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APA

Stebbings, H. (2026, October 10). How to Build a Sales Machine | Max Freeman, Ramp [Interview transcript]. 20VC with Harry Stebbings. CEOInterviews.AI. https://ceointerviews.ai/interview/3032550/

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Harry Stebbings. "How to Build a Sales Machine | Max Freeman, Ramp." 20VC with Harry Stebbings, 10 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3032550/.

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@misc{stebbings2026_3032550,
  author       = {Harry Stebbings},
  title        = {How to Build a Sales Machine | Max Freeman, Ramp},
  howpublished = {Interview transcript, 20VC with Harry Stebbings. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3032550/},
  note         = {Speaker-attributed transcript with timestamps}
}