All episodes of The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2026-10-10 · 68 min · 13,029 words

20Sales: Inside Ramp's Sales Playbook: How to Build a $1.7BN ARR Sales Machine with Max Freeman, SVP Sales @ Ramp

Listen to the original audio · Transcribed with NVIDIA Parakeet · Timestamps stay in sync with the live audio

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 two X what a standard SDR is gonna make. But guess what? You got to book forty, fifty, sixty meetings, which is four to six times what a standard SDR has to book. There are some sellers at Ramp that are on fifteen 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. 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 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. 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 20 VC. 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 forward slash two zero VC. If you want to redline NDAs, MSAs, DPAs, and any other procurement contracts faster, go to Crosby.ai forward slash two zero VC. 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 well the last twenty 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.

That is the first couple of minutes. The rest is $1.

We already have this episode, so unlocking it is cheap and permanent: the full transcript (68 minutes, 13,029 words), segment and word-level timestamps, and .txt, .srt, .vtt and word-level JSON downloads, as many times as you like, forever.

No account needed, we create one from your checkout email. With credits it is 1 credit; packs start at 10 episodes for $5, and monthly plans are cheaper still.

get it now

Ready in about two minutes.

Pay once, no subscription. Credits never expire.

See all plans Monthly from $9, about 23 cents an episode

Secure checkout by Stripe. No account needed: we create one from your email. By paying you agree to the terms.