Conversation
Highlights

In this episode of How I Hire, Andy Mowat speaks with Melissa Rosenthal, Co-Founder at Outlever and former CRO at Cheddar and Chief Creative Officer at ClickUp, about her approach to vetting executive talent. Drawing from her transition from BuzzFeed creative leadership to sales leadership, Melissa shares how she vibe-coded a Lovable app that filtered 1,000 applicants to 20 candidates, why she requires minimum 10 back-channels before offers, and her view on growth leader tenure at scaling stages.

Topics discussed:

• Why hiring VPs from ServiceNow-scale companies for startups consistently underperforms, and the profile with “really good success”: candidates who’ve worked at enterprises but chose Series B/C startups, showing they grasp both corporate infrastructure and startup pace.
• The 15-minute “biggest project” question covering what the candidate did, team composition, individual roles, and outcomes, designed to expose ego when candidates position themselves as “the center and the hero” while gathering names for back-channeling.
• How Melissa and her co-founder vibe-coded a Lovable app in two days requiring candidates to answer two questions without previewing or redoing them, filtering 1,000 submissions down to 20 completions and three successful hires.
• The controversial growth marketing reality: “there’s a tenure that exists within that role…you can probably get the most out of them for two years” before needing someone who’s scaled your next stage, as finding leaders who’ve scaled 0 to 500M “is probably not really realistic.”
• The minimum 10-person back-channel protocol for VP roles: five who worked adjacent, two superiors, and two peripheral colleagues, with “no offer until the back channel is complete” after learning from having to rescind previous offers.
• Why she will “never hire a fractional person” for VP roles at high-growth companies where she’s “barely sleeping,” as fractional means “they’re not all in,” though agencies work for tactical gaps once solid leadership exists.
• The “hardest thing you’ve gone through” question designed to “open up a world of like this person’s gonna bare their soul,” revealing resilience and EQ critical for all go-to-market roles she hires.
• Why most founder hires didn’t work out: candidates aren’t transparent despite clear “work life imbalance” warnings, “rotten leaders” who treat teams poorly, people “always in the car” suggesting outsourced work, requiring her “trust and respect” leadership approach.

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