The Real Reason Your Revenue Team Is Failing/Bridget Winston - Metrics, Cheetahs, B2B+B2C ~ Spark of Ages Ep 65
We sit down with Bridget Winston to unpack what separates a real Chief Revenue Officer from a bookings-focused sales leader, and why the org chart tells you the truth faster than the job title. We get practical about SaaS metrics, AI-driven go-to-market, and the leadership habits that keep teams performing as the playbook keeps changing.• Evaluating a CRO remit by reporting lines and revenue accountability• Using GRR and NRR to diagnose product-market fit and ICP clarity• Treating revenue as a lagging indicator of customer centricity• Preparing for LLM-driven discovery with brand, PR, and earned media• Testing AI tools that shrink territory and quota planning cycles• Shifting budget from paid ads to community-led growth and local events• Turning customer testimonials into repeatable social proof loops• Managing humans and AI agents with specific, camera-ready feedback• Fixing incentives and systems before blaming the team• Creating urgency with day-five impact expectations instead of tired 30-60-90 plansYour org chart can tell you whether you’re hiring a true Chief Revenue Officer or just renaming a VP of Sales. We sit down with Bridget Winston, CRO at Patient Now and a three-time CRO, to get brutally clear on what revenue ownership actually means and why “bookings” is a dangerous north star when retention and expansion are what compound.We dig into the SaaS metrics that expose reality fast: GRR, NRR, LTV to CAC, and how boards interpret dashboards when product-market fit and ideal customer profile are still shaky. Bridget shares a sharp reframing that stuck with us: revenue is a lagging indicator of customer centricity. From there, we zoom out to the “SaaS-pocalypse” conversation and what happens to pricing, planning cycles, and revenue per employee as AI turns some companies into dinosaurs and others into cheetahs.Then we get tactical about the LLM era of B2B discovery. If buyers are finding software through ChatGPT-style answers, Reddit threads, G2-style reviews, and YouTube, we need consumer-grade brand building, PR, and community-led growth that creates earned media AI can’t ignore. Bridget also breaks down AI tools she’s used to compress territory planning and quota work from months to weeks, plus AI coaching that improves call quality and handoffs without blowing up day-to-day operations.We even take a fun detour into Spark Tank wine trivia, then bring it back to leadership: how to give feedback with real specificity, fix systems before blaming people, and set expectations for day-one impact. Subscribe, share this with a revenue leader, and leave a review so more builders can find the show.Bridget Winston: https://www.linkedin.com/in/bridgetwinston/Bridget Winston is the Chief Revenue Officer at PatientNow, leading go-to-market and customer-facing teams across a rapidly growing vertical SaaS platform in the fast-expanding $20 billion aesthetics and wellness industry. A three-time CRO with over 20 years of experience, Bridget was formerly the CRO at Chief, where she led membership growth and helped the company reach a $1.1 billion valuation. During her tenure, Chief was recognized by TIME as one of the 100 Most Influential Companies and by Fast Company as one of the Most Innovative Companies. Before that, Bridget served as the CRO at Shutterstock, growing revenue to $300 million.Website: https://www.position2.com/podcast/Rajiv Parikh: https://www.linkedin.com/in/rajivparikh/Email us with any feedback for the show: sparkofages.podcast@position2.com




