<p>On this episode of BILLIONS, I’m sitting down with Reggie Marable, the Chief Revenue Officer at Sierra. </p><p>Reggie’s path wasn't a straight line. He went from being a professional linebacker in the CFL to working in a Sprint call center, and eventually rose to become the Head of Sales for Slack North America. After years at Salesforce, he walked away to join Sierra as employee #23.</p><p>Founded by Bret Taylor (former Salesforce Co-CEO) and Clay Bavor, Sierra has reached a $10B valuation and is on a path to $100M ARR in just seven quarters. </p><p>Their secret? A business model that should terrify every legacy SaaS founder: Outcome-Based Pricing. </p><p>In this masterclass, we break down:</p><ul><li>The Sierra Sprint: How to scale to a $10B valuation in record time.</li><li>Service as Software: Why Sierra only charges customers when a problem is actually resolved.</li><li>The Sales Shift: Why Reggie left a massive leadership role at Slack for an early-stage startup.</li><li>Hiring for the AI Era: Why Reggie looks for "humble, hardworking, and low-ego" talent over pedigree.</li><li>The Recovery: How getting fired earlier in his career became the foundation for his $10B mindset.</li></ul><p><br /></p><p><strong>TIMELINE :</strong></p><p>00:00 – "If your dreams don't scare you...": The Muhammad Ali mindset.</p><p>01:17 – From the CFL to a Sprint call center: Reggie’s raw beginnings.</p><p>04:07 – The "fired" moment: How losing his job led to a total reinvention.</p><p>05:33 – The Salesforce &amp; Slack era: Mentoring 200+ people and scaling Slack North America.</p><p>10:00 – Why Reggie left Slack to become employee #23 at Sierra.</p><p>12:23 – Outcome-based pricing: Why the "per seat" model is dying.</p><p>16:20 – AI agents in the wild: Real-world results for Cigna, Singtel, and Sonos.</p><p>19:00 – The resolution model: Charging for solved problems, not software access.</p><p>31:15 – Operational cadence: How a $10B startup manages its weekly rhythm.</p><p>35:50 – Hiring strategy: Why "humble and hardworking" beats high-ego sellers.</p><p>44:10 – The "diversity" advantage: Building high-performance teams through inclusion.</p><p>47:16 – Reggie’s final advice: "Success is a winding road."</p><p><strong>REFERENCES :</strong></p>