Conversation
Highlights

In this episode of How I Hire, Andy Mowat speaks with Robin Bordoli, CRO & CMO at Weights & Biases, about his engineering-informed approach to hiring senior GTM talent in AI-native companies. Drawing from his experience leading revenue organizations through IPO at Marketo and Jive, plus CEO roles at Nextroll and Figure 8, Robin shares his five-element pre-search system and how he applies optimal stopping theory to make mathematically rigorous hiring decisions.

Topics discussed:

• Why VP of Field Engineering is the hardest GTM hire, requiring leaders who can manage four distinct technical roles (solution architects, pre/post-sales solution engineers, forward-deployed engineers) while balancing deep technical acumen with commercial instincts that most candidates spike one direction or the other.
• The mandatory five-element pre-search framework executed before meeting any candidates: JDs written from scratch with force-ranking criteria (specific program spend, pipeline targets, ARR stage), hunting grounds, minimum five sample profiles ranked against the JD, interview process with decider/inputs/socializers explicitly designated, and role-specific take home exercises.
• How to design AI-resistant take home exercises using open-ended scenarios (annual planning with constraints for demand gen, live sales positioning with 10 minutes prep for PMM) requiring 1-3 hours prep plus live presentation, where synthesis quality and trade-off articulation matter more than the artifact itself.
• The three-round interview structure optimized for 9-hour total candidate investment, with Round 3 socializers serving as the final gate where candidates can expose naivete about equity/board dynamics or reveal poor judgment through inappropriate requests.
• Why external recruiters provide three strategic advantages beyond sourcing: accessing passive candidates planning six-month professional exits, providing market intelligence on whether hundreds or five people fit specialized criteria, and creating trusted advisor dynamics where candidates reveal vulnerabilities they won’t share internally.
• Applying optimal stopping theory (the 37% rule) to sequential hiring decisions: estimate total qualified candidates meetable in your timeline, interview the first 37% to calibrate on the strongest, then extend offer to the next candidate exceeding that benchmark.
• Three executive diagnostic questions that expose readiness: “What four adjectives appear in a word cloud from everyone who knows you well?” “Where were you the best and worst versions of yourself and why?” “What are your decision criteria and where does your current role fall short?”
• The counterintuitive onboarding framework that prevents executive failure: explicitly contract for 30-90 days where the only ask is listening and learning, while concurrently assigning a first project that’s in their wheelhouse but requires cross-functional engagement to balance psychological safety with purposeful integration.

ABOUT YOUR HOST: 

Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating. 

Learn more about about Whispered: www.whispered.com

Interact with AI Andy: www.whispered.com/whisper-search