Kyle Norton, CRO at Owner.com and a former sales leader at Shopify, shares his expertise in systematic hiring processes for high-velocity sales environments. He reveals his 'hire 18 months ahead' framework that helped scale Owner.com and discusses how traditional sales performance metrics can mislead hiring decisions. Leveraging Kahneman's principles, he emphasizes structured evaluations to minimize bias. Additionally, he advocates for quarterly hiring analyses to refine talent assessment and improve overall accuracy in hiring.
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question_answer ANECDOTE
Pulled-Forward SVP Hire To Unlock Bottlenecks
Kyle hired an SVP of Go-To-Market Strategy from HubSpot because he was personally a bottleneck.
The hire unlocked initiatives Kyle couldn't lead full-time and accelerated strategic work.
volunteer_activism ADVICE
Hire 18 Months Ahead At Scale
For companies >$20M ARR still doubling, hire someone who can do the role needed in 18 months.
Over-hire seniority now so they can level up as the company scales.
insights INSIGHT
AI Creates More Work, Not Smaller Teams
AI increases capacity, so teams do more, not fewer tasks, following Jevons' paradox.
Short-term leverage improves productivity but competitors quickly replicate the advantage.
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In this episode of How I Hire, Andy Mowat speaks with Kyle Norton, CRO at Owner.com, about building systematic hiring processes that overcome cognitive bias in high-velocity sales environments. Drawing from his experience scaling Owner.com from $20M to approaching $50M ARR while maintaining 2.5X year-over-year growth, Kyle shares data-driven frameworks for evaluating talent in SMB-focused sales organizations. His approach reveals how structured processes and post-hire analysis can dramatically improve hiring accuracy when traditional interview methods fail.
Topics discussed:
The "hire 18 months ahead" framework for companies above $20M ARR still doubling - specifically how Kyle hired an SVP of Go-to-Market Strategy from HubSpot to unlock initiatives he was personally bottlenecking, demonstrating when to pull senior hires forward versus waiting.
Kyle's counter-intuitive discovery through quarterly hiring analysis that sales craft performance in case studies was non-predictive of role success - leading to a complete restructuring toward evaluating "psychotic work ethic," organizational skills, and coachability over traditional sales acumen.
The systematic bias-fighting approach using Kahneman's principles: independent scorecarding across five company values, asking identical questions in identical sequence, and providing the same feedback to all candidates to create controlled comparison environments that prevent halo effect contamination.
Kyle's quarterly "hiring autopsy" process where RevOps correlates interview scores from all stages (recruiter screen, hiring manager, case study, bar raiser) against actual performance metrics, then conducts 90-minute outlier analysis sessions to identify process gaps and manage blind spots.
The champion-based hiring model that explicitly avoids consensus decision-making - where bar raisers provide structured feedback on specific criteria but hiring managers retain full ownership, preventing diluted accountability while maintaining quality control.
Kyle's "mutual references" system including his template that lists every direct report and counterpart from his career, granting candidates permission to source their own references while requesting the same access - plus his specific back-channel questions like percentile ranking among all functional peers.
Why cold calling the functional hiring manager remains the highest-conversion candidate strategy, and how Kyle's systematic LinkedIn content creation (generating 40-80K impressions per job post pre-algorithm change) created hiring flywheels that sourced 80% of initial IC team through network effects.
The shift toward hiring new graduates over experienced reps when backed by heavy enablement infrastructure - Kyle's data showing university hires ramp faster than experienced SDRs due to coachability and lack of bad habits, supported by strong enablement team investment.
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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