WisconsinCIO ORBIE Leadership Award recipient: For Frank, Rimerman + Co. CIO Allen Smith, the best measure of leadership is relationships
When Allen Smith reflects on his career, he doesn’t measure success by the technology he built or even the size of the teams he led. He measures it by the relationships that lasted.
“We work in a relationship business,” said Smith, Chief Information Officer at Frank, Rimerman + Co. and recipient of the 2026 Wisconsin ORBIE Leadership Award. “Being the best in a given tech stack can only take you so far. Being a great colleague, a great mentor, a great teammate—that's what builds your reputation throughout your career.”
That philosophy has shaped a career spanning more than three decades, from building some of the earliest technology systems at organizations that never had them, to growing Baker Tilly’s IT team many times over. Along the way, Smith has focused as much on developing people as he has on developing technology.
From technology “firsts” to team builder
Smith’s path into technology was somewhat accidental.
After graduating from Michigan State with a finance degree, Smith entered a challenging job market for finance positions. A recruiter noticed his technology background, including a Fortune 500 internship, and encouraged him to retool his résumé for tech roles. He landed his first technology job as an application developer at a Chicago-based insurance company.
What kept him in the field, however, was different than what got him into it.
“I stayed because it never stops changing, and because the impact felt tangible in a way I don't think I'd have found anywhere else,” he said. “That's what turned a job I stumbled into a bit by accident into one I’ve built my life around.”
Early in his career, Smith built first-generation technology infrastructure for organizations that had never had it before, including email platforms, voice and call-routing systems, networks and internet presences.
But his career eventually entered a second chapter, one focused more on people. When Smith joined Baker Tilly in 2001, there were 18 people in IT. Nearly 24 years later, the team had grown to about 250.
“The number I’m proud of isn’t 250 — it’s that several of my direct reports at the end of my tenure came from those original 18,” he said. “We grew together, and we grew the culture together, and it held.”
Lessons learned and other “Allen-isms”
For Smith, developing people is one of the most important responsibilities of any leader. His approach starts with giving people their “first chance.”
“I am proud of my record of hiring non-traditional backgrounds,” he said. “In order to give someone a second chance, shouldn’t you give them their first?”
Smith also believes leaders should “never take credit” and “never delegate failure”. In his words, “Your success is due to everyone around you. Any failure is due to your leadership failure. You are not the star of the team, the people on the team are the stars.”
Relationships outlast the work
Smith's influence extends well beyond his own organization. He served as chair of WisconsinCIO from 2022 to 2025 and is now emeritus chair, and he has sat on boards for Baker Tilly International, Intapp, and Workday. Closer to the ground, he stays active in mentoring and community work, including volunteering with i.c. stars, a nonprofit workforce development program for underserved young adults.
Over three decades, many of those working relationships have quietly turned into personal ones—colleagues who stayed in his life long after the work that first brought them together. For Smith, it all comes back to where he started. “A lot of technologists believe they're in a technology field,” he said. “But I've come to see it differently. We work in a relationship business.” Technology changes every few years, he noted; but the relationships compound.
The proof isn't any system he launched or team he built. “It's not what you built, but who's still in your life when the projects are long finished,” he said. “That, to me, is the real measure of a career in this field.”