Real Alpha
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20VC · 2 min · Oct 10, 2026

Decompose a rep's number to separate talent from order taking

MF

Max Freeman

SVP of Sales, Ramp

Joined Ramp as its first sales hire and was leading 300+ salespeople by 2025.

  • Harry StebbingsHost · Founder, 20VC

    Built a venture firm on his podcast; its third fund closed at $400M.

About this segment

Max describes how he tests whether a candidate's results were real. He breaks down their quota by source and has them reconstruct deals chronologically, including a deal they lost.

From “How to Build a Sales Machine | Max Freeman, Ramp”, Oct 10, 2026. Watch the full episode

“you have to decompose their number. And so, okay, you did 2 million. That's great. How much of it was inbound? How much of it was outbound?”
MFMax Freemanat 9:25 · 20VC9:25

Takeaways

  1. Split their number by inbound, outbound, expansion and founder-sourced
  2. Make candidates rebuild two deals step by step in order
  3. Ask about a lost deal; weak reasons signal weak sellers
Watch 1:36 from 9:25

In this episode

Full episode

  1. 9:25Decompose a rep's number to separate talent from order taking1:36

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Transcript

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

  1. 9:37

    Yeah, you have to decompose their number. And so, okay, you did 2 million. That's great. How much of it was inbound? How much of it was outbound? How much of it was expansion? How much of it was sourced by your founder? How much of it was from existing opportunities that you inherited? And then you really have to drill down such that you can spot and figure out if someone is bullshitting you. And then to get even more deep into testing their acumen around sales, it's all right, talk to me about two deals.

  2. 10:06

    You have to make them reconstruct them chronologically. The best candidates give so much texture and like you're really trying to figure out, well, how did you advance this? Well, what was it? Were you articulating business value? Was it some workflow that you tied to a business outcome? They'll know that. And if they can't describe that, not a good sign. The inverse is also true. You want to understand.

  3. 10:26

    Talk to me about a deal that keeps you up at night. Why did you lose it? If they can't unpack why they've lost an opportunity, was it they were single threaded? They didn't build a champion. There was no business value. The product wasn't good enough. They didn't qualify well enough. Like figuring that out and testing for it is actually incredibly important in an interview process. What if I said to you, hey, I get you. One of the decision makers is friends with a competitor.