The Front Lines
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Melissa Rosenthal.
Co-Founder · Outlever
I'm a media and tech executive building a platform to counter the frustrations I've dealt with throughout my career. Previously, I was the CCO of ClickUp, CMO of Insight Timer, CRO of Cheddar and VP, Creative at BuzzFeed. I've been featured in Forbes' 30 Under 30, Business Insider’s 30 Most Creative People Under 30, and Digiday's "Changemakers." I've always been obsessed with the idea of net new value creation and enabling brands to own the conversations they care about while reaching their ideal customers. This passion led me to co-found Outlever. We transform brands into the #1 news source their industry, enabling them to own the conversations their customers care about at an unprecedented scale, and give them the ability to establish true authority and reach key audiences in meaningful ways. Simply put, we open a net-new marketing and sales channel for ROI-focused B2B and B2C brands by turning companies into the voice of their industry.
Guest
Melissa Rosenthal
Co-Founder
Company:
Outlever
Location:
San Diego, CA
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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:

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

Five takeaways from this conversation.

Actionable for Whispered Hiring founders

  1. Build Custom Screening Tools When Traditional Methods Consistently Fail
    Melissa and her co-founder spent two days vibe-coding a Lovable app that required candidates to answer two questions on video without previewing them or redoing responses. Out of over 1,000 submissions, 99% were blank videos from people who couldn't answer unprepared. Twenty people completed it, 10 were solid, and she made three hires from that batch. When standard hiring produces disasters despite good resumes, create friction that reveals real capability.
  2. Conduct Minimum 10 Back-Channels Before Extending Any Offer
    Melissa requires minimum 10 references for VP roles: "a mix of the five people that have worked adjacent to them, two that have worked above them, and then two that have kind of worked around them or worked with them in adjacent roles." She finds peripherals most revealing because they show how someone was viewed organizationally. As she states: "There's no offer until the ba
  3. Accept That Growth Leaders Have Finite Scaling Ranges
    Here's what most won't admit: "there's a tenure that exists within that role and then you need to cycle through to the next person and I think you can probably get the most out of them for two years." Someone who scaled 0-50M rarely has the playbook for 100M-500M. Instead of forcing fractional solutions (which she will "never hire" for VP roles because "they're not all in"), recognize when to transition to leaders who've scaled your next stage.
  4. Use the "Biggest Project" Question to Expose Ego and Gather Intelligence
    Melissa asks candidates to spend 15 minutes detailing their largest accomplishment: who was on the team, what each person did, what succeeded and failed. When candidates position themselves as "the center and the hero," it's "a pretty good indication that like that's not the right person." This simultaneously tests player-coach mentality and provides names to back-channel for role verification.
  5. Avoid Hiring Enterprise Executives for Hyper-Growth Startup Roles
    Melissa has found "less luck with hiring VPs and senior level roles when I hire them from other large companies where I'm hiring them at a scaling hyper growth startup." The operational pace and player-coach expectations don't translate from companies like ServiceNow. The profile that works: candidates who've experienced both enterprise operations and Series B/C startups, demonstrating they understand where you're headed and where you actually operate.

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