Hire proven execs or grow your own?

In this episode of Whispered Hiring, Andy Mowat speaks with Heather Doshay, Founder of Waypoint Works and former VP of People at Webflow and Head of Talent at SignalFire, about identifying and developing high-slope talent. Heather introduces her PEAKS framework for spotting individuals whose growth rate matches or exceeds company trajectory, and challenges conventional hiring wisdom on everything from why charisma can be a trap to how pairing up-and-comers with advisors often outperforms hiring proven executives.

Topics discussed:

• The PEAKS framework for identifying high-slope talent: Persistence, Emotional grounding, Action orientation, Knowledge orientation, and Systems thinking. Candidates spiking in three can be high potential, but truly high-slope individuals demonstrate all five.
• Why "shiny object syndrome" derails executive hiring. Companies interview candidates and form roles around them rather than first defining what the role needs to solve over the next 24 months.
• The case for pairing up-and-coming executives with experienced advisors through equity arrangements rather than defaulting to "seen-the-movie-three-times" hires who may be tired and less immersed in new capabilities like AI.
• How to detect candidates who have lost their fire. Listen for verbal signals like "looking for a change of pace," watch response times, and ask directly: "Tell me the last time you faced burnout. What was happening?"
• Why charisma is deliberately excluded from the high-slope framework. Sales candidates especially can wow interviewers while lacking actual capabilities. Structured competency-based questions with a clear rubric prevent likability bias from overriding signal.
• The two bookend questions that reveal everything. Open with "Why this role? Why this company? Why now?" to assess intent and build your closing script. End with "What questions do you have?" If they have none or ask something from the homepage, Heather's done.
• Why high-slope talent requires organizational readiness. These individuals push boundaries, beg forgiveness rather than ask permission, and surface problems constantly. Without cultural values that honor this behavior, the org will reject them.
• The rigidity reframe on ageism. It's not age that creates hiring risk. It's rigidity. A 25-year-old can be just as set in their ways as a veteran executive. Name flexibility as a competency and design questions to assess it directly.

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

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