Whispered Hiring with Jessica Chiew, Head of GTM Strategy & Operations @ Canva

In this episode of Whispered Hiring, Andy Mowat speaks with Jessica Chiew, Head of GTM Strategy & Operations at Canva, about her rigorous approach to hiring builders in product-led growth environments. Drawing from her experience scaling GTM operations at Asana and Canva, Jessica shares tactical frameworks for testing whether candidates can truly execute versus simply tell polished stories, structuring ops teams that span product and enterprise motions, and designing onboarding that delivers impact in the first 90 days. Her insights reveal how calculated vulnerability and continuous team evolution drive both individual performance and organizational velocity.

Topics discussed:

• How to test for customer journey fluency in PLG environments by asking candidates to describe the journey at their previous company, then present a live scenario where 260 million MAUs already exist in your domain and watching whether they shift from MQL/SQL language to customer-centric thinking.
  
  
• The "rocks and rubble" test for builder mentality. True builders describe scenarios where multiple crises hit simultaneously (missing quarterly target, product launch, doubling headcount, losing office space) and frame it as energizing rather than overwhelming, versus managers who cite isolated quarterly challenges.
  
  
• Jessica's signature 30-minute interview structure starting with "I've read your professional background, can you quickly talk me through your story and path to today's conversation" where failure states include reading their resume back for 20 minutes or lacking intentionality about how to use limited time.
  
  
• The four to five layer questioning depth that reveals hands-on leadership. Starting with "what does the future of customer success look like?" then drilling through implementation details, measurement approaches, and roadblocks encountered until candidates either demonstrate project-level ownership or reveal they're reciting refined talking points.
  
  
• Why making yourself available during case study prep is a conversion predictor. Jessica offers her cell phone number for 30-minute prep calls, 20% of all candidates take her up on it, but 50% of successful hires do, simulating their actual working style and investment level before they join.
  
  
• The continuous team restructuring philosophy where Jessica constantly reevaluates scope and structure every six months as the business evolves, maintaining team trust through upfront vulnerability about business gaps, personal motivations, and explicitly asking for flexibility while keeping career growth top of mind.
  
  
• The four-element onboarding pack that drives first-90-day impact. A written narrative of business state and their role in it (not just verbal), explicit 30/60/90 expectations including quick wins, full repository of QBRs and dashboards for self-service, and a sequenced listening tour spreadsheet with every stakeholder meeting pre-planned by week.
  
  
• The portfolio staffing approach for balancing pattern recognition with execution capability. Mixing enterprise veterans with startup athletes across the team while testing experienced hires for builder traits through SQL proficiency as a proxy for hands-on work and ensuring they have startup experience somewhere in their background to prove they can operate without massive resources.

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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