Conversation
Highlights

In this episode of How I Hire, Andy Mowat speaks with Eric Gilpin, President GTM at G2, about his systematic approach to executive hiring built on 22 years of sales leadership at companies like Upwork and CareerBuilder. Eric shares his contrarian philosophy on recruiting directly from your customer base, his specific four-stage VP+ interview process that treats candidates as collaborators rather than supplicants, and why he maintains relationships with his next three hires before roles even open. His insights reveal how leveraging conversation intelligence tools and transparent back-channeling can transform executive hiring outcomes.

Topics discussed:

• Why recruiting from your customer base provides a competitive moat. Eric actively evaluates every customer CRO and CMO he meets for potential fit, and uses Gong as a “cheat code” to review two years of recorded customer calls before initial conversations.

• The role design framework that prioritizes team capability gaps over individual credentials. Eric audits his entire leadership team for gaps in AI literacy, data-driven thinking, or emotional intelligence before defining what each new executive hire must bring to raise the bar across the organization.

• How Eric maintains an “always on” executive pipeline by knowing his next three VP+ hires right now despite all roles being filled. This eliminates reactive recruiting and prevents managers from hoarding talent due to lack of pipeline.

• The four-stage interview process for VP+ hires: 30-minute relationship call, context deck deep dive with 15 slides of non-public data, panel of no more than three people, then collaborative working session on real business problems where output gets used in actual kickoffs or strategy.

• Why executive search agencies are non-negotiable for senior hires despite cost. Agencies handle initial vetting so conversations focus on co-authoring roles, plus they maintain year-round relationships with passive candidates and access to unlisted opportunities in the private market.

• The outbound gap revealing selection bias in funnels. Despite 20 open roles generating thousands of monthly applicants, Eric receives only one quality outbound per month, yet he forwards every single one because the effort signals exactly what GTM roles require.

• The transparent back-channel approach where Eric tells candidates upfront “I’m going to poke around, you should too” and asks what’s off limits. He never outsources this to recruiters to control market noise and hear context firsthand.

• Why cross-functional customer journey reviews must precede GTM hiring. Eric runs weekly reviews covering the entire funnel with every function present, tracking 90 days forward given G2’s 66-day sales cycle plus 28-day speed to lead, ensuring aligned input metrics before making hires.

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