After recently being promoted from inside to outside sales, Wyatt has once again hit an important milestone, transitioning to a Senior Account Manager. Serving our Southern Alberta clients and leading the Stride Capital/Servus Credit Union referral program, Wyatt brings a high level of commitment and a strong work ethic to everything that he does. We asked him a few questions about his transition, what he’s learned, what’s been most fulfilling, and his advice for others looking to make a similar jump. Keep reading to learn more.

1. What made you want to transition to outside sales initially? 

I’d been in inside sales for a long time, and I loved the pace and the learning curve. Running a broker desk doing about $90MM a year taught me a lot. But after a while, I wanted to get out from behind the screen and actually meet the people I was helping.

Outside sales felt like a chance to build real relationships, not just move deals. Southern Alberta has a lot of strong communities and hardworking business owners, and I wanted to be out there with them, not just on email.

2. What has the transition from inside sales to outside sales looked like for you?

Honestly, it’s been energizing. It’s a different rhythm, for sure. Instead of spending my whole day at a desk, I’m on the road, in branches, meeting vendors, and getting to know business owners face‑to‑face.

I’m still using the same skills I developed during my time in inside sales, like structuring deals, communicating clearly, and staying organized. But now I’m also building the pipeline myself, instead of actioning whatever comes in. Leading the Stride/Servus referral program has been a big part of that too. It’s rewarding to connect with branches and help their members in ways that feel collaborative, not transactional.

3. At Stride Capital and in the equipment financing industry, what are the key differences between inside and outside sales?

Inside sales is very fast-paced and technical. You’re juggling emails, calls, approvals, documentation, and more. You learn to be quick and accurate because you don’t really have a choice.

Outside sales is more about showing up and being present. It’s relationship-first. People don’t work with you because of a rate, they work with you because they trust you and know you’re consistent.

Both roles matter, they’re just different beasts.

4. How has your experience working in inside sales prepared you for outside sales? What lessons or skills have you learned or developed that have set you up for success?

Inside sales gave me the best foundation I could’ve asked for. When you’re handling high volume, you figure out very quickly how to prioritize, how to communicate clearly, and how to solve problems without overthinking.

Some skills that transferred really well include:

Those abilities help a lot in the field. People appreciate when you’re easy to work with and you don’t drop the ball.

5. During your transition, what was A) most surprising B) most challenging and C) most fulfilling for you? 

A) Most surprising:
How much small, simple touchpoints matter. A five‑minute visit or a quick check‑in goes a long way.

B) Most challenging:
Balancing being out in the field with staying on top of everything behind the scenes. You can’t let your responsiveness slip just because you’re on the road.

C) Most fulfilling:
Seeing the impact firsthand. When you help a Servus member or a local business get the equipment they need, and you’ve met them in person and seen their operation, so it feels different. You see the real value of the work you’re doing each day. 

6. What advice would you give to someone looking to do a similar transition? 

Take the tools you learned in inside sales and run with them. If you already understand urgency, follow through, and staying organized, you’re already ahead of most people. 

Above all, be honest with people. Clients appreciate straight answers, even when it’s not what they hoped to hear.  Do not over promise and under deliver. Transparency builds long-term relationships.

And just have fun with it. Meeting people is genuinely the best part of this job.

Learn more about Wyatt and get in touch today.