Job Search Retro: GTM Strategy & Operations

Alex landed a Manager of GTM Strategy & Operations role at a late stage cloud infrastructure company.

Hedgy Member Background

• Recent MBA grad with prior experience in venture capital, working across portfolio companies on go-to-market projects. Intentionally used business school internships to become a builder and learn to "prompt to code".
• Was exploring GTM strategy & ops and chief of staff roles across a wide range of stages, from seed to late stage.
• Received 6 intros through Hedgy, reached multiple final rounds.

Key Insights

AI case studies: build in reverse, and assume the analysis is table stakes

• Nearly every loop included an AI-native exercise. They fell into two camps: demonstrating broad proficiency with tools like Claude Code or Codex by building a small app, and structured data cases deliberately designed so the AI output alone isn't the differentiator.
• His approach was to work in reverse. Everyone probably starts by plugging in the data and info provided by the company. This leads to interviewers reviewing a dozen candidates and seeing small iterations of the same AI generated deck. Instead, scaffold the analysis or recommendation the way you would do it without AI. Define your structure, inject insights from your experience, and then incorporate the provided data last and polish from there.
• Go in assuming the interviewer will assume your numbers are right. The differentiation is the "so what" beyond the analysis. In one rev ops case (territories, deal stages, win rates), instead of stopping at "focus on bigger deals, they close at a higher rate," he layered in the channel strategy he had actually used to attack similar accounts.

In GTM interviews, lead with what you've built, not frameworks

• The MBA or ex-consulting/banking instinct is to open with a framework and stay at a strategic altitude. Early on he realized this was hurting his chances. Interviewers would rather hear something you actually did and built, even if it's not an apples-to-apples match.
• On GTM tool stack questions (e.g. Clay, HubSpot, Apollo), he was never grilled on hands-on proficiency. What mattered was designing a system and explaining where each tool would plug in.

Narrow early to manage interview fatigue

• His one do-over is he didn’t begin to narrow his search until he already felt interview fatigue. It was a good problem to have but being in multiple final round loops may have impacted his ability to have put his best foot forward. The turning point was a simple filter: only speak with companies where you'd take the job if they offered it tomorrow.
• The volume of conversations did have a silver lining. With each loop he got better at recognizing where he performed well and made incremental improvements, which made the final stretch far more efficient.

This post is part of our job search retro series where Hedgy members who have recently started a new job share learnings from their search. If we can be helpful as you navigate your search, email us at founders@hedgy.works