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$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 :
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By Guillaume MoubecheOn 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 :