In this episode of How I Hire, Andy Mowat speaks with Guy Yalif, Chief Evangelist at Webflow and former co-founder of Intellimize (acquired by Webflow), about his precision-engineered approach to executive hiring in marketing. Drawing from leadership roles at Twitter, Yahoo, and BrightRoll, plus an unconventional career path from aerospace engineer to CMO, Guy shares specific frameworks for evaluating senior marketing talent across product marketing, demand gen, brand, and comms.

His insights reveal how to assess whether candidates genuinely understand AI tooling versus surface-level ChatGPT usage, why traditional case studies fail in 2025, and how to implement "SIM" interviews that actually predict on-the-job performance.

Topics discussed:

The four core marketing specialties framework for executive hiring: product marketing (messaging, positioning, value prop), demand gen (paid, organic, SEO), comms, and brand. Why clarifying a candidate's "wheelhouse" matters more than checking boxes, and ensuring they'll hire people better than themselves in weaker areas to round out the team.
Why product marketing is the hardest marketing discipline to hire for: the feedback loop takes 6+ months to see if messaging shifts drive business impact, "great" looks deceptively similar to "good" during interviews, and the role splits into two distinct types (inbound/strategic versus outbound/launch execution) that use identical terminology.
The "altitude assessment" interview technique: listen for whether candidates answer at market dynamics and business impact level versus spreadsheet mechanics level, then deliberately ask follow-up questions to force altitude changes and identify where they have genuine depth versus rehearsed talking points.
How the "SIM" (simulated meeting) approach fixes broken case studies: give candidates ~1 week on a real scenario, explicitly tell them to use you as a resource ("ping me off hours, ask anything"), and judge the prep conversations as heavily as the final presentation to see how they synthesize, ask questions, and handle ambiguity rather than how well they prompt ChatGPT.
The framework for assessing stage-readiness: look for experience at both large companies ("seen it done really well") and startups ("scrappiness and grit"), then test if their muscle memory matches your stage by listening for whether they describe slicing roles into multiple people (big company reflex) or being hands-on with zero direct reports (startup reality).
The blind reference process that works: tell candidates upfront you'll contact people they didn't introduce, ask what's off-limits to protect their current job, then do 3-5+ references. When one reference is surprisingly negative, do 4-5 more to determine if it reveals a pattern or says more about that specific reference-giver.
Why tracking consistency and variety of storylines separates real performers from interview performers: watch for candidates who tell the same story with different data to different interviewers (red flag), and assess whether they have multiple strong examples across situations or just one or two polished go-to stories indicating limited depth.
The "magic wand" question that cuts through performance: "If you could craft the perfect next gig that had you happy to go to work every day, irrespective of this discussion, what's that job look like?" This surfaces genuine alignment, reveals rote regurgitation, or uncovers the one critical dimension they haven't voiced that might be a dealbreaker.

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

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