In this episode of Whispered Hiring, Andy Mowat speaks with Doug Hanna, Former President at Kustomer, the AI powered customer service platform acquired by Meta and since spun out independently. Drawing on executive roles at Zendesk and Grafana, Doug shares the hiring frameworks he has built through hard experience, covering role design, leveling, recruiter selection, and reference strategy.
Topics discussed:
- The three part executive role design framework Doug adapted from Cole Group: top two year outcomes (specific and measurable), a minimum experience threshold kept internal and never shared with candidates, and culturally specific attributes. The internal alignment this creates is what actually compresses time to hire.
- Why two years is the only defensible planning horizon in high growth companies. Optimizing for a leader who can take you public when you are at $10M ARR reliably produces the wrong hire for the stage you are actually in.
- How Doug handles leveling without losing the person: the reframe he uses is that even post leveling, the person is still in the biggest role of their career, and will be in an even bigger one twelve months later. He involves them in interviewing their replacement with an explicit upfront contract: demonstrate maturity and you have a real voice; become obstructionist and you are out.
- The operating altitude test as a better proxy for "builder" than anything AI related. The executives Doug most respects move from board level strategy to personal Gong call review without waiting for someone to surface conclusions for them.
- Why specialist recruiters win: Doug looks for a recruiter who personally knows 60 to 70 percent of the candidate list. The question he recommends asking peers when selecting a search partner: "Which recruiters do you actually return calls from?"
- Radical transparency as a hiring principle. Surprises do not benefit anyone. Doug tells candidates upfront that back channels will happen, then asks them to predict what he will hear. The gap between expectation and reality is its own signal.
- A pattern most hiring managers underestimate: Doug has encountered a non-zero number of candidate supplied references that were not positive. He treats this as a failure on multiple levels and calls every single reference provided, every time.
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.
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