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."

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