How to Build a Sales Machine | Max Freeman, Ramp

Summary · 2 min read instead of 1 h 12 m

Max Freeman is SVP of Sales at Ramp, which he joined as its first sales hire after quitting a mid-market account executive job to become an SDR again. By 2025 he was leading more than 300 salespeople and had helped build Ramp's sales organisation from the ground up.

Freeman argues that sales is increasingly an engineering, data infrastructure and math problem, and describes how Ramp built internal automation for outbound and pre-call research to free seller capacity. He makes the case for hiring mispriced talent such as investment bankers and top sellers from high-growth companies with low NPS, paying above market in return for far higher output. He advises founders to put early reps on 100% OTE with no quota, hire sellers in pairs, verticalize only once market share starts to cap opportunities, and compress cycles through rigorous qualification. He also explains Ramp's 60 to 90 day onboarding, rep-to-cost ratios of seven to 12, a forecasting system within a 5% delta, and his own push to stop jumping into every deal.

Minute by minute

1. 8:56

   Decompose a candidate's number. To separate real sellers from order takers, Freeman breaks down a candidate's quota into inbound, outbound, expansion, founder-sourced and inherited deals. He asks candidates to reconstruct two won deals chronologically and explain a lost deal. Ramp then runs a business case discovery call testing research, selling fundamentals and whether he would buy from the person.

2. 23:02

   Verticalize later than most do. Freeman argues companies verticalize far too early when they are still in land-grab mode. He suggests doing it around three to 5% market share, when the pool of opportunities becomes contained and conversion becomes the lever, as Oracle, Workday and SAP have done.

3. 47:16

   Customer success drives expansion. Freeman disagrees with Dagnan's view that customer success should be paid services. Ramp's CS team is highly technical, including CPAs, and he sees it as the engine for NDR and earning the right to cross-sell new products after a strong deployment.

4. 49:44

   Forecasting accountability and status quo losses. Freeman credits finance counterpart Asher with models consistently within a 5% delta, and says forecasting accuracy is part of seller performance reviews. Ramp dropped forecasting calls and runs weekly pipeline reviews focused on at-risk and lost deals. He says Ramp mostly loses to the status quo, which means sellers failed to create urgency.

5. 58:48

   Stop jumping into every deal. Freeman says his biggest weakness is the instinct to personally take over important problems, which can teach people to wait for him. He still expects leaders to be a dual threat and sends at least five cold emails a day himself. He credits exposure to Eric and Kareem and accountability for his founder-like mindset, and cites Dave Schneider's three categories: "you are God", don't know yet, or fired.

Published Oct 10, 2026.