Conversation
Highlights

In this episode of How I Hire, Andy Mowat speaks with Alina Vandenberghe, Co-CEO of Chili Piper, about building high-performing remote teams through radical transparency and unconventional talent development. Over 10 years of scaling Chili Piper into a leading demand conversion platform, Alina has developed contrarian approaches to executive hiring, from requiring GTM leaders to pass technical competency tests to sharing complete financial data during interviews. Her insights reveal how treating internal promotion as the default path, rather than external hiring, creates both stronger leadership and better cultural alignment.

Topics discussed:

• Why Chili Piper opens their entire data room to all employees, including cash runway, churn rates, and board decks, and how this transparency enables SDRs to develop executive-level thinking and grow into VP roles within the company.
• The “electrons and protons” framework for role optimization: identifying energy-giving versus energy-draining tasks for each employee, then strategically deploying fractional specialists and AI agents to handle the draining work while maximizing individual impact zones.
• How to evaluate remote work readiness beyond the resume: screening for intrinsic motivation through storytelling passion, why office experience is non-negotiable for junior hires, and the correlation between self-directed learning and remote success.
• The technical competency requirement for all GTM executives, including testing CMOs and CROs on JSON and JavaScript understanding, to ensure they can credibly engage with RevOps buyers and technical stakeholders.
• The three-part framework for evaluating departure stories: verifying honesty through back-channel references, assessing ownership versus blame mentality, and gauging compassion toward their current employer as a predictor of future behavior.
• Why leading with questions rather than data during executive interviews reveals strategic thinking: asking candidates what metrics they need rather than presenting your board deck shows how they prioritize and think about the business.
• The paradox of building a fully remote company while prioritizing in-person recruiting at industry events, using stage presence and dinner interactions as leading indicators of cultural fit and relationship-building ability.
• The intensive onboarding approach where new executives spend multiple days at Alina’s home, observing founder-mode operations firsthand and understanding how personal mission integrates with business execution, plus explicitly communicating where founder support ends and external mentorship begins.

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