About Jason Whitehead
Organizations don’t struggle with CRM or AI because the technology is bad. They struggle because people, data, and operating habits don’t change.
My work sits at that intersection. I help leaders turn complex systems into tools their teams actually use, trust, and rely on to drive real business results.
Drive Adoption. Realize Success.
Early in my IT career, I was focused on the technology. Getting systems configured and live was the key to success. It had to be on-time and on-budget. Nothing else mattered.
Then, while working as an internal CRM systems manager at Texas Instruments, my boss came to me and said, "Jason, it is great you have the system up and running. But if you can't get people to use it, and the executives don't see value from it, we don't need it - or you. So you better figure it out!"
These words changed my life and my career.
That moment hit me hard. I realized adoption wasn’t about training or communication campaigns - it was the key to unlocking technology value.
From that point on, I shifted my entire focus to helping leaders ensure their systems were actually used in ways that created measurable business outcomes. I’ve been helping organizations and SaaS vendors do that ever since.
That experience showed me something important: technology succeeds or fails not because of its features, but because of how people use it.
Why leaders typically come to me
Leaders usually reach out when:
• CRM or AI investments are live, but results are underwhelming
• Teams don’t trust the data and work around the system
• Adoption fades after launch and never fully recovers
• A system technically works, but the original business problem was never solved
• AI feels promising, but risky to scale without stronger foundations
In most cases, the issue isn’t the tool. It’s how work actually gets done around it.
What I bring to the work
I’ve spent decades working across customer success, revenue operations, and technology adoption, helping organizations bridge the gap between strategy and execution.
My background combines deep experience in change and adoption with hands-on work around CRM, revenue systems, and operational workflows. That allows me to move comfortably between executives, operators, and frontline teams and translate intent into action.
I’ve worked with organizations such as BP and Texas Instruments, supporting teams as they recover value from stalled systems, improve adoption, and create operating models that hold up under real-world pressure.
How my background Shapes The Way I Work
Getting a system live is rarely the hard part. Making it matter is.
Over the years, I’ve been brought into organizations at different stages:
Before major system launches where adoption needed to be done right the first time
After CRM implementations are live, but the systems are not used and not delivering needed business value
During AI pilots where leaders needed confidence the foundations were solid before scaling
My story and milestones
I’ve spent my career helping organizations navigate change, implement technology, and get people to work differently so the business actually benefits.
Along the way, I’ve led and advised teams across customer success, operations, and go-to-market functions. I’ve seen firsthand how even well-funded initiatives can stall when adoption is treated as an afterthought, and how quickly momentum can return when teams are aligned around clear outcomes.
This perspective shapes how I approach every engagement. Practical, grounded, and focused on results that last beyond go-live.
Beyond Client Work
I’m also the co-host of the Breakthrough SaaS Growth podcast, where I explore what actually drives adoption, customer outcomes, and long-term value in modern organizations.
The conversations reflect the same themes that show up in my work every day: technology moves fast, but sustainable results still depend on people and how work gets done.
Let's Talk
If you’re responsible for making CRM or AI work in practice, not just in theory, I’m always open to a conversation to see whether I can help.
