Jason Wickman

I'm Jason Wickman — a revenue operator who's spent 25 years in the seat, not above it. My career started with more than a decade at Microsoft selling Dynamics 365 into the Fortune 1000, going head-to-head with Salesforce, SAP, and Oracle. I learned how enterprise revenue actually moves — and where it quietly leaks.

After Microsoft I became a principal at Atrio/NuSoft (later acquired by Avtex), then took an operating-partner equity stake in a Microsoft-aligned CRM consultancy and drove its transformation from a technician-led shop to a growth-mindset commercial organization — scaling it from $1M to a $14M exit. From 2022 to 2025 I led sales for Alithya's US Microsoft practice, one of the largest in North America, delivering Dynamics 365 and Power Platform work across hundreds of clients.

Today I run Agilidy — fractional CRO services and the Brad AI revenue diagnostic — while building Orkastra.AI, a platform of AI-native revenue orchestration agents that help B2B sellers turn account intelligence and CRM data into repeatable revenue. I arrived at the Challenger methodology independently, 15 years before it was published. My bet is simple: earn the meeting, don't automate the noise.