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What does it take to run 60% of a company?
Garrett Marker, Chief Revenue Officer at Brex, oversees about 700 people across sales, customer success, RevOps, partnerships, enablement, and support - and this year, his goal was to aggressively scale a sales team that industry data recently ranked the third-fastest growing in tech, without letting rep performance slip. It hasn't all gone to plan. Garrett is refreshingly candid with host Josh Schachter, grading the scaling effort a "B" - what held up, what broke, and how his team turned around a slumping segment in dramatic fashion. Along the way, he explains why the battle cards that used to last a quarter now go stale in about a week, why Brex bet on human SDRs while the market rushed toward AI ones, and why the hardest part of AI products isn't selling them at all.
It's a look inside the operating decisions of a CRO whose remit spans the entire customer lifecycle - from first touch through renewal and expansion.
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What You'll Learn
- How a struggling Brex segment did two months' worth of revenue in eight days and the AI-assisted diagnosis behind the course correction
- Why battle cards that used to last a quarter are now stale within about a week
- How AI role plays and automated call scoring turned weeks or months of rep ramp into hours or days
- Garrett's build-vs-buy rule
- What Brex's internally built "narrative platform" does that seller-productivity tools don't (mapping the full buyer's journey across sales, CS, and support)
- The question Garrett asked at the end of every demo as a seller and the rep whose career it transformed in three months
- How the TAP program works
- Why adoption, not sales, is the bottleneck for AI products
- How a shift in CS conversations (not product changes) grew book-closing adoption 20% in twelve months
- What Garrett believes it will take to increase NRR by 30 points in the next couple of years
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Timestamps
0:00 - Preview & Intro
1:52 - Meet Garrett Marker (CRO, Brex)
4:03 - Why founders buy like consumers
5:28 - Scaling the third-fastest-growing sales team in tech
7:28 - Solving today's AND tomorrow's problems
9:25 - 2 months of revenue in 8 days after a segment course correction
11:22 - How AI made competitive diagnosis faster
14:37 - Rebuilding enablement around AI and ramping reps in days
17:27 - How Brex decides build vs. buy
18:35 - Mapping the full buyer's journey across sales, CS, and support
21:38 - Success plans and buyer psychology
25:56 - Why won't you move forward?
27:53 - How SDRs earn on-the-spot promotions to AE
32:52 - Post-sale priorities: cracking AI product adoption at scale
35:11 - Why CS teams must understand the whole tech stack, not just their product (+20% book-closing adoption)
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Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com
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Where to Find the Guest
Garrett Marker: https://www.linkedin.com/in/gmarker/
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Where to Find the Hosts:
Josh's LinkedIn: https://www.linkedin.com/in/jschachter/
Unchurned Substack: https://unchurned.substack.com/
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