$100M ARR in 7 quarters: inside the $10B AI machine - Reggie Marable [Sierra]

On this episode of BILLIONS, I’m sitting down with Reggie Marable, the Chief Revenue Officer at Sierra. 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.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. Their secret? A business model that should terrify every legacy SaaS founder: Outcome-Based Pricing. In this masterclass, we break down:The Sierra Sprint: How to scale to a $10B valuation in record time.Service as Software: Why Sierra only charges customers when a problem is actually resolved.The Sales Shift: Why Reggie left a massive leadership role at Slack for an early-stage startup.Hiring for the AI Era: Why Reggie looks for "humble, hardworking, and low-ego" talent over pedigree.The Recovery: How getting fired earlier in his career became the foundation for his $10B mindset.TIMELINE :00:00 – "If your dreams don't scare you...": The Muhammad Ali mindset.01:17 – From the CFL to a Sprint call center: Reggie’s raw beginnings.04:07 – The "fired" moment: How losing his job led to a total reinvention.05:33 – The Salesforce & Slack era: Mentoring 200+ people and scaling Slack North America.10:00 – Why Reggie left Slack to become employee #23 at Sierra.12:23 – Outcome-based pricing: Why the "per seat" model is dying.16:20 – AI agents in the wild: Real-world results for Cigna, Singtel, and Sonos.19:00 – The resolution model: Charging for solved problems, not software access.31:15 – Operational cadence: How a $10B startup manages its weekly rhythm.35:50 – Hiring strategy: Why "humble and hardworking" beats high-ego sellers.44:10 – The "diversity" advantage: Building high-performance teams through inclusion.47:16 – Reggie’s final advice: "Success is a winding road."REFERENCES :Muhammad Ali Jay-Z Dr. Martin Luther King Jr. Brian TracyAlbert EinsteinNelson MandelaBrett TaylorClay BavorRyan RaddingElliot GreenwaldLily WangStephanie EvansGreg MarshMandy St. Leger Morehouse College Canadian Football League SprintSalesforceSlackSierraCigna Next SingtelAfrotech & Sistas in Sales