Bryan Cox is the VP of Worldwide Sales at Braintrust, the eval and observability platform that builders and frontier model providers alike rely on to ship AI agents. Before Braintrust, Bryan spent nearly five years at Grafana, joining at Series A/B and helping build one of the most respected go-to-market motions in developer tooling. Earlier in his career he cut his teeth selling complex cloud and data-center infrastructure, including a stint at Flexera, learning what large strategic "whale-hunting" deals look like in action. A former college tennis player and self-described history major who fell into sales, Bryan treats the work like the craft it is, and is moving his family from Santa Barbara to the Bay Area to get closer to the action.

Timestamps:

(00:00) Cold open: the one-click "no" that exploded a seven-figure deal

(01:22) Welcome to the Crew podcast + sponsors

(02:52) From early cloud computing to Flexera's whale-hunting deals

(06:02) Why Grafana produced so much elite sales talent

(07:23) Choosing Braintrust: going where the highest-value problem is

(09:34) Job as craft: loving the technical, hard-to-understand sale

(13:31) What separates great reps from good ones on enablement

(14:35) Sales as an ultramarathon: balance, burnout, and your "why"

(22:05) The motion offense: circling a deal instead of running waterfall

(25:08) The seven-figure deal that died, and operationalizing champions

(29:41) How to interview a company: TAM, durability, and who's buying

(33:10) The 40-call diligence process before joining Braintrust

(36:50) Why everyone's moving to voice agents for ramp and enablement

(42:25) The AI tool stack and a hot take on too much DIY

(44:21) Rapid fire: GTM teams he admires and what he tests for in hiring

(46:47) "Why are you in sales?" and the Shrek/onion test

(50:44) The most creative way to break into Braintrust (hint: it’s not through Bryan)

About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies.

Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today.

No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.

About CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.

Where to Find Crew

LinkedIn: https://www.linkedin.com/company/crewgtm

YouTube: https://www.youtube.com/@thecrewgtm

Newsletter: https://www.withcrew.blog/

Website: https://www.withcrew.ai/

This episode is brought to you by the following sponsors:

Dust

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