Whispered Hiring with Ryan Westwood, CEO @ Fullcast

In this episode of How I Hire, Andy Mowat speaks with Ryan Westwood, CEO and founder of Fullcast and serial entrepreneur who previously scaled Simplist to over $600 million in revenue. Ryan reveals his systematic approach to M&A and executive hiring, including why he uses physical activities to assess mindset beyond polished interviews and maintains a multi-decade spreadsheet of talent observed in authentic contexts. His frameworks demonstrate how maintaining six executives with 10+ year tenure creates compound advantages in speed and decision-making.

Topics discussed:

• Using physical activities to reveal authentic leadership beyond interviews: Why Ryan uses VR skydiving for acquisition target CEOs and walking or fly fishing for executive candidates. These contexts bypass the "professional interviewer" problem where senior leaders have refined responses across 25+ similar conversations. Ryan notes: "I will find without fail, I will learn very insightful things. I've never been on a walk in an interview process where I didn't pick up on really great nuggets that I never gathered in the interviews."
  
• The decisive integration framework for M&A success: After vetting the CEO, the critical success factor is decisive clarity on two variables: the CEO's specific role going forward and whether products will integrate. The failure zone is ambiguity or the "middle ground." If a CEO is tired after 15 years, that's acceptable if explicitly acknowledged upfront rather than pretending continued enthusiasm while the team detects misalignment through actions.
  
  
• The compounding advantage of hiring one executive at a time: Ryan has never hired more than one executive in a year time frame, maintaining six executives with 10+ year tenure. This creates asymmetric advantages: zero political dynamics, executives who proactively solve problems without CEO involvement, and bandwidth to deeply support the single new hire versus the typical scenario of simultaneously training four executives competing for attention.
  
  
• The board composition question that reveals company dynamics: Ryan walks through how to decode company risk, culture, and power dynamics by understanding board makeup (common vs. preferred seats, independents, investor types). The specific question to ask during interviews: "Tell me about the board you've constructed." This single question reveals more about a company's trajectory than hours of other diligence.
  
  
• The repeat executive diagnostic for vetting CEO quality: When evaluating offers, ask "How many people are repeat executives for you?" If a CEO built a unicorn but zero executives from their prior company joined their next venture, that's a signal about working relationship quality. Ryan's six long-term executives each received double-digit equity stakes, creating aligned economics beyond typical executive compensation.
  
  
• Maintaining a talent observation system across decades: Ryan keeps a spreadsheet of impressive operators observed in non-interview contexts: cubicle colleagues who stayed focused during company chaos, HR consultants who delivered executive-caliber presentations, people demonstrating character in everyday situations. This becomes the first hiring source because authentic behavior reveals more than performative interviews.
  
  
• The 50-page CEO Operating Rhythm document for accelerated onboarding: Ryan maintains a living document covering his complete operating philosophy, department-specific frameworks, decision-making preferences, and working style. New executives review relevant sections to compress the getting-to-know-you period from years to weeks. Supplement with daily check-ins initially, weekly video calls, and mandatory first-week meetings with all other executives who report observations back to Ryan.

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