What he says

Founders “misdiagnose the opportunity to acquire customers as something related to conversion rates.” If you needed one deal and it pushed, you should have had five, “so that if three of them close, you finish way over target.” [10:11] “If you have a company worth building, there's like 100 times more customers that you could be talking to than you're talking to.” [11:14]

What he says

Going from 10% to 20% conversion “sounds like you're improving by 10% but you're actually doubling” — it means retraining reps or the founder getting “far better at pitching and closing.” Doubling leads is easier if the market is big enough. [11:34] “I would rather deliver two times the number of leads to a rep and have their conversion rates come down slightly.” [12:46] Judge on outcome: “There aren't pictures on the scorecard.” [13:15]

What he says

Setting undifferentiated opportunity goals meant “more lower quality opportunities that converted at lower rates that led to less revenue.” He grades early Zenefits RevOps “a D plus.” [17:43] At Brex he started RevOps early: pattern-match the companies and personas that convert, then point the targeting there — “where we pointing our missiles.” [18:04]

What he says

1. Google, Meta and LinkedIn ads are “easy, low-friction, not creative, everyone is doing it… the lowest ROI, a fairly efficient market.” [53:25]

2. “Early on, I would try and bucket like 100% of the marketing spend” on things that directly benefit the prospect. Billboard vendors and ad platforms benefit no one you're targeting. [55:15] Monaco Invitational: $100K prize pool, 100 players, 8 of 9 finalists were customers. [56:46] Referrals at $2,000 each are “my favorite bill to approve.” [57:52]

His process

• At least one “big splashy” campaign a month [49:15]
• A marketing committee — can be just the co-founders
• Everyone brings two ideas to a whiteboard; eight ideas, pick two or three
• A failure is “a win because you learned”

Why most companies don't

Two excuses: “I'm not good at this, I'm an engineer,” and “I don't want to light money on fire.” His answer: “No one starts being an expert at this stuff.” [47:30] The plane was a bounded bet — “worst case it's a $60,000 learning.” [51:42]

What he says

“If you aren't educating the buyer on how to onboard, receive value, and ultimately buy your product, the customer doesn't know how to buy your product.” [63:19] Bring a “happy path” from today to fully onboarded, map it together, then ask what's missing (security, procurement, legal). His sample: meeting two shows a pre-built custom environment → two-week trial with agreed outcomes → onboard the rest. The most common founder problem: “I've followed up three times… ‘give me a week.’ A week passes.” [64:42]

Truthful urgency [65:14]

“Much of sales is psychology,” and “we certainly never want to say anything that is untrue or misleading.” His script: “We are onboarding three customers into our pilot this month. Two spots are spoken for. I can't guarantee the spot if you don't speak for it today.”

Nautilus: this is simply true for us — onboarding capacity per month is finite (POS connections, SMS registration, site build). Name the number of slots and the date. Never invent one.