(Jill Cummings ~ 2019 Award Winner)
As CBN celebrates our 19th year of honoring young business leaders in Central Oregon, we — along with our sponsor, Washington Trust Bank — thought it would be fun to reach out to some of our past award winners and ask…
Where Are They Now?
What advice would you give to your former self at the time you were featured as an Accomplished Under 40 Award recipient?
Don’t be afraid to take on new challenges. Explore opportunities that may push you outside your comfort zone. Growth often happens when navigating unfamiliar territory and taking calculated risks. Use the momentum from the award to fuel future endeavors and set new, bigger and more ambitious goals that challenge and inspire you to keep pushing forward. Cultivate genuine connections with your peers. Build a strong support system within your industry and personally.
What has changed the most in Central Oregon since then?
In terms of population growth — everything. Central Oregon has experienced a significant influx of people and businesses which has brought change in the form of both new opportunities and challenges. What hasn’t changed is the need for authentic community. If anything, it’s needed now more than ever. That’s why I’m proud Summit Bank expanded to Redmond in 2024 while keeping the same core model we started in Bend in 2015: relationship-based, community-first banking. Staying local, listening and taking care of your customers still matters.
How has your career and community involvement changed since you were selected?
The nature of my involvement has evolved, but the commitment has stayed the same. Like life, it ebbs and flows — some years are heavier with board service, others with volunteer work or mentorship. But I’ve never stepped away from being engaged. That is a non-negotiable for me. I believe leadership means showing up where you’re needed, even when it’s not convenient.
What did it mean to you to receive the award?
It meant the world. Not just because of the recognition, but because someone I respected took the time to see me, to believe in me and to nominate me. That kind of support is incredibly meaningful. It was a moment that reminded me how much impact we can have on each other’s lives — just by showing up, speaking up and lifting up one another.
What are some of your proudest accomplishments that make you who you are today?
At the top of the list is my family. Watching one of my sons get married and the other graduate from high school has been a beautiful reminder of what matters most. Professionally, stepping into the SVP, Commercial Banking Team Leader role and helping lead the growth of our bank has been fulfilling. The bank’s expansion to Redmond–where we have raised our family–has been highly successful and meaningful. It’s not just about expansion; it’s about deepening roots in a place I call home.
What advice would you give to this year’s — and future — recipients of the Accomplished Under 40 Award?
Don’t shy away from doing the hard stuff. Show up when it’s not easy or flashy. Volunteer. Mentor. Say yes, and raise your hand. It’s amazing to discover the next doors that open after you step through the first one by being receptive to something new and even uncomfortable. The titles and achievements are great, but what really lasts is the impact you have on others and the legacy you help build in your community.
What question would you ask yourself for this interview?
Who inspired you along the way, or supported you when you needed it most?
None of us become “accomplished” alone, especially in business. I think it’s important to reflect on the people — colleagues, mentors, friends, family — who poured their experience, knowledge and wisdom on us when we were still figuring it out. Then we ask ourselves: how can we be that person for someone else now?
