Most Workday professionals assume the technical ladder only goes one direction: deeper specialization.
But what if it doesn’t?
In this episode of Workday Gold, I sat down with Chris Lennon, Regional Sales Director at Kainos, to talk about his journey from QA tester to consultant, to product owner, to sales leader.
And here’s what stood out.
Sales Isn’t What You Think It Is
Chris didn’t move into sales because he loved quotas or negotiation tactics.
He moved because he enjoyed helping customers solve problems.
That’s an important distinction.
When you come from a technical background, you don’t approach sales as “pushing features.” You approach it as discovery. You understand the customer’s configuration challenges. You speak their language. You empathize with their constraints.
That credibility changes the dynamic.
The Ask Gets Easier When Trust Exists
One of the biggest fears technical professionals have about sales is “the ask.”
When do you say, “Are you ready to buy?”
Chris admitted that it was hard early on. Especially delivering big pricing numbers.
But when you build real relationships first, the pricing conversation becomes a natural next step, not an awkward sales pitch.
Relational selling is very different from cold outbound business development. And for many Workday professionals, it’s a far more natural fit.
Product Thinking Is Different Than Services Thinking
We also discussed Built on Workday apps and the distinction between services and products.
Services are project-based. You build, deliver, and move on.
Products require roadmaps, ongoing support, enhancements, and long-term investment.
That shift in mindset is significant — and it opens new career paths: product owner, roadmap manager, SaaS sales, customer success, and more.
Career Growth Doesn’t Happen Accidentally
The biggest takeaway?
Opportunities rarely land in your lap.
You have to:
- Back yourself.
- Ask for opportunities.
- Build your network early.
- Stay open to paths that don’t look traditional.
The Workday ecosystem is bigger than most people realize. And sometimes your next step isn’t deeper technical — it’s adjacent.
If you’re curious about career transitions, relational selling, product thinking, or simply how to navigate growth inside the Workday ecosystem, this conversation is worth your time.
Listen to the full episode to hear the stories behind the lessons.
Keith Bitikofer is a Workday coach and consultant who helps professionals navigate their careers in the Workday ecosystem. Listen to the Workday Gold podcast for more insights on career transitions and leadership development here
Want to learn more from the Workday ecosystem? Connect with Keith Bitikofer on LinkedIn for ongoing insights about Workday support and team management.