Brake or Accelerator? The Most Important Question a GC Will Answer in 2026

Lawyers participate in the downside and never the upside, and Jason Barnwell argues that is the single most important thing about to change. David Cowen sits down with Jason, the former Microsoft GM and associate GC who now leads legal at Agiloft, to unpack why the GC role is being rewritten around upside risk, why contract intelligence is becoming business intelligence, and why the legal leaders selling signal back to the enterprise will earn a seat at the CFO's table. Key Topics Covered: Upside risk vs. downside risk: Why legal moves from brake to accelerator and what that changes Probabilistic practice: Accepting outcomes that are less than perfect to open the aperture on what legal can do at scale Contract intelligence as business intelligence: How aggregated contract data becomes a strategic asset The cut line: How budget conversations reward the best stories — and what legal needs to do to stay above the line Storytelling as leadership: Lessons from Microsoft legends Brad Smith, Neil Suggs, and Hossein Nowbar Selling signal back to the enterprise: Packaging contract data into predictive insights that earn legal upside participation Faster deals as legal's superpower: Why predictive contracting becomes the GC's new currency 🎧 Subscribe on Apple Podcasts, Spotify, or wherever you listen. Share this episode and take your career from now to next! 💡To learn more about the future of legal innovation, visit https://solid.legal/podcasts/ Never eat alone!