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2024 Leadership Advancements

posted by TrueNorth Companies on Monday, February 12, 2024

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TrueNorth leadership aspiring and aligning to something greater.

At TrueNorth, we take pride in cultivating talent that impacts and inspires the many communities and industries we serve. This year, we are proud to feature three newly appointed executives and their instrumental role in helping TrueNorth achieve new heights and explore what’s possible.

“We have taken executive-level stability to heart as we prepare TrueNorth for everything the future holds,” said Jason Smith, CEO of TrueNorth. “It’s a privilege and an honor to announce these significant leadership advancements that will serve to fuel and strengthen TrueNorth’s planned trajectory in the years and decades to come.”

Three appointments took place effective January 2024: Robynn Westphal, TrueNorth’s General Counsel and Lead Counsel for our Transportation Division has been appointed the role of Chief Legal Officer. Chris Gulker, Transportation Practice Leader has assumed the role of Executive Vice President of Transportation. Samantha Rogers recently joined TrueNorth as Vice President of Human Resources. Trent Tillman, formerly the Executive Vice President of the Transportation Division, now serves as TrueNorth’s President and Chief Revenue Officer. Randy Rings, TrueNorth’s former CLO, will remain on the board as Secretary and has accepted the role of Managing Director working alongside Executive Vice President Dru Bridges in TrueNorth’s First MainStreet platform.

These promotions took place in January as part of TrueNorth’s thoughtful and deliberate approach to developing exceptional talent internally and positioning the firm for the future.

Robynn Westphal

Chief Legal Officer

As TrueNorth’s Chief Legal Officer, Robynn oversees contracting; negotiations; sophisticated program structures; insurance policy interpretation and coverage analysis; regulatory issues; claims and litigation; policy creation and implementation; while playing an active role on the firm’s many committees. Prior to CLO, Robynn served as TrueNorth's general counsel and lead counsel for the firm’s Transportation division.

Upon receiving degrees from Cornell College and Drake University, Robynn Westphal joined TrueNorth in 2006, after spending the first few years of her legal career in general practice. Robynn is a member of the Trucking Industry Defense Association (TIDA); the Transportation Lawyers Association (TLA); the Council of Insurance Agents and Brokers (CIAB); and the Iowa State Bar Association. Robynn also serves on the board of directors for Matthew 25, the nonprofit’s Cultivate Hope committee, and is a proud member of the Daughters of the American Revolution. Robynn and her husband, Chris, share a blended family with five children.  

“I am honored to have been appointed Chief Legal Officer of such an incredible organization.  My 17 years at TrueNorth have provided me an opportunity to learn directly from the firm’s founders, collaborate with skilled teams to provide exceptional service and achieve professional and personal growth with the support of TrueNorth’s executive team. I will continue to use these valuable lessons and experiences to lead TrueNorth's legal initiatives, leveraging the team’s integrity and talent to provide TrueNorth support and guidance.”

Chris Gulker

Executive Vice President, Transportation

As Executive Vice President of TrueNorth’s Transportation division, Chris Gulker oversees the strategic direction of the division. Chris Gulker has been an integral part of the TrueNorth family for over a decade, contributing his expertise exclusively within our Transportation division. His journey with TrueNorth began over 10 years ago and over the years, his dedication and strategic insights have played a pivotal role in guiding the firm's approach to supporting trucking companies and drivers.

“I am honored and excited to take on the role of Executive Vice President for TrueNorth’s Transportation division. My years at TrueNorth, dedicated to working with the drivers we serve, have given me valuable insights into shaping effective strategies for supporting trucking companies and their drivers. I am committed to driving innovation and excellence in our services as we continue to navigate the dynamic landscape of the transportation industry.”

Samantha Rogers

Vice President of Human Resources

Last December, we announced Samantha Rogers had joined TrueNorth as Vice President of Human Resources and a key member of the firm’s Executive Leadership Team. Over the course of her career, Samantha has offered key insight and guidance to many organizations throughout the Eastern Iowa Corridor. We believe this unique perspective serves to strengthen our vibrant culture and reinforces our commitment to colleague learning and development. This senior leadership role further defines TrueNorth’s ambitions to be a career destination while offering colleagues clarity and confidence they need to contribute to the firm’s growth and success.

“The culture at TrueNorth is electric. I’ve always enjoyed watching TrueNorth grow and evolve into one of the best workplace cultures in our region. I look forward to being a contributor to their mission and exploring new heights as an executive member of the TrueNorth team.”


About Author

TrueNorth is the largest insurance and financial services firm of its kind based in Eastern Iowa. Today, our dedicated staff consists of over 350 colleagues and is organized so each becomes a specialist in their respective practice areas. This collaboration offers our clients a coordinated approach to risk management, insurance services and financial strategies. 

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