6 quotes from 1 episode on 20VC with Harry Stebbings, each with a timestamped link to the source.
6 quotes1 episode
The short version
Enterprise sales losses happen when reps fail to create urgency against customer inertia. Max Freeman reported that Ramp assigns a dedicated growth engineering team to build internal tools like Ramp Revenue for pre-call research.
Most interesting insights
Outbound prospecting historically centered on writing messages and placing phone calls.
“Outbound used to primarily be a writing and a calling problem…”
Max Freeman, 20VC with Harry Stebbings · October 2026 · Watch at 18:05 ↗
Dedicated growth engineers build custom software for sales reps
Ramp maintains an internal growth engineering team focused on sales tools. Max Freeman pointed to Ramp Revenue, an internal operating system the engineers built to perform pre-call research.
“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…”
Max Freeman, 20VC with Harry Stebbings · October 2026 · Watch at 21:54 ↗
Failing to build urgency loses deals to customer inertia
Max Freeman stated that Ramp loses to the status quo when sales reps fail to create urgency during the deal cycle.
“…the majority of the time we're losing to the status quo, which is on us. That's not a product gap. That's a we need to look ourselves in the mirror. We did not create enough urgency.”
Max Freeman, 20VC with Harry Stebbings · October 2026 · Watch at 52:51 ↗
Enterprise deals rarely die to rival software. Freeman points out that when Ramp loses, "the majority of the time we're losing to the status quo, which is on us. That's not a product gap. That's a we need to look ourselves in the mirror. We did not create eno…
Quota productivity ratios between 7:1 and 12:1 come from running sales as an engineering problem, staffing teams with former investment bankers and sellers from low-NPS competitors.
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