20Sales: Inside Ramp's Sales Playbook: How to Build a Sales Machine with Max Freeman, SVP Sales @ Ramp
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
October 10, 2026
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. Ramp's latest reported revenue exceeds $1.7BN, with a valuation of over $40BN.
Speakers Max Freeman, Harry Stebbings
TopicsInvestingBusinessNewsTech News
Max Freeman (0:00)
There's three categories of performance in sales. One, you are god. Two, I don't know yet. Or three, you're fucking fired. We'll pay 2X what a standard SDR is gonna make. But guess what? You gotta 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 Beane. Sales is very much an engineering problem when you break it down. It's a data infrastructure problem. It's a math problem.
Harry Stebbings (0:30)
I have had enough. I've had enough of podcasts being fluffy. I want them to be granular and I want to learn very specifically how to excel across different disciplines. 20 Sales takes you inside the world of the best sales leaders. 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. But 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. But before we dive into the show today, today I want to tell you about how the first AI law firm, Crosby, helped us close a big sponsor. As you know, some of the biggest companies in the world advertise on 20VC, my British dulcet tones clearly convert well. I was working to close this big sponsor and they wanted to get through legal review quite quickly to close the deal. Crosby turned red lines around in three hours and caught major issues that would have caused us serious problems in the future. Crosby combines AI, some of the best engineers in the world, from companies like Ramp and Stripe and some of the best attorneys in the world from top 10 law firms. Customers get the best of both worlds. An elite human attorney reviews every contract, but they move incredibly quickly returning red lines in under four hours. They help the fastest growing companies like Cognition, Ramp and Clay close deals in hours, not weeks. Learn more at crosby.ai/20vc.
If you want to redline NDAs, MSAs, DPAs and any other procurement contracts faster, go to crosby.ai/20vc.
It's speed that you can really trust. While Crosby keeps your numbers sharp, OneMind keeps your customer conversation sharper. Our friends over at OneMind have a hot take. The B2B GTM model we've been using for the last 20 years. It's collapsing. Predictable revenue isn't so predictable, and buyers are just tired of explaining themselves at every handoff between SDRs, AEs, CSMs and support. You feel it in your board reporting, your sellers feel it in their coverage, your buyers feel it as they wait for answers. Well, enter OneMind and their GTM superhumans. HubSpot, Alteryx and ZoomInfo are just three of the tech companies using OneMind superhumans to qualify buyers, ride along with sales reps and coach customers. Whether you're ahead of target or under pressure to increase bookings ahead of hiring or behind on target even, and need every rep to hit quota, OneMind is the solution. See for yourself at onemind.com. That's onemind.com.
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Max Freeman (4:24)
You have now arrived at your destination.
Harry Stebbings (4:27)
Max, I am so excited for this dude. I think when people think of the fastest growing companies, they do immediately think of Ramp. 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?
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