The Twenty Minute VC · Oct 10, 2026 · 72m · 61m saved
With Max Freeman, SVP of Sales, Ramp
Ramp pays some of its sales development representatives twice the going rate and expects them to book four to six times as many meetings as a typical rep.
Most startups fill early sales jobs with people from other software companies. Ramp's first sales hires included investment bankers from Goldman Sachs and Citi, and engineers who automated the work of finding and emailing prospects.
"Sales is very much an engineering problem when you break it down. It's a data infrastructure problem. It's a math problem."
Max Freeman quit a mid-market account executive job in 2020 to start over as a sales development representative at Ramp, which sells corporate cards and finance software to chief financial officers. He now runs sales there as senior vice president, overseeing teams in which some reps take 15 or more calls a day.
The full interview is covered here so you can skip it. 72 minutes of audio, 11 minutes of reading.
Here are the 13 lessons that matter.
Key Takeaways
Ramp hires investment bankers as sellers and pays them above market for far more output
Freeman said bankers work long hours, have business sense and carried weight when cold-calling finance chiefs
He recruits top sellers from companies that grew despite weak products
Those reps had to create their own demand and sell at a premium price
He told sellers to pick a company by its market, its talent and its founders, not by title or equity
Outbound selling is now an engineering problem, he said, and Ramp keeps at least six engineers on it
A conversion rate just under 1% from email to booked meeting is a strong result
Founders should skip quotas for their first two quarters and hire sellers in pairs
Ramp pays 2x to 3x quota credit on new products to get them off the ground
New reps face 60 to 90 days of boot camp and cannot get accounts until they pass certifications
Ramp's quota-to-pay ratio runs 7 to 12 times, with some inside reps at 14 times
Ramp loses most deals to the status quo, which Freeman called a failure to create urgency
An internal tool cut pre-call research from as much as 30 minutes to 90 seconds, and the saved time goes into higher quotas
Freeman still sends at least five cold emails a day and said leaders who stop selling lose their teams
1. Hiring Bankers as Sellers
Freeman said Ramp's early sales team drew heavily on investment bankers, and several now run large parts of the business. He gave three reasons: bankers are used to long hours, they bring business sense, and a former Goldman Sachs banker calling a finance chief cold made a strong impression for an unknown company.
Ramp pays these hires well above market, and expects far more in return
"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." — Max Freeman
Down-market reps still book well above 50 meetings a month, he said. Inside and commercial sales reps take 10 to 12 calls a day.
