TrueNorth Announces Next Phase of Leadership Succession Plan

posted by TrueNorth Companies on Tuesday, February 13, 2024

(Cedar Rapids, Iowa, February 2024) - TrueNorth Companies, L.C., a closely and privately held risk management and insurance brokerage firm headquartered in Cedar Rapids, Iowa, is proud to announce more leadership advancements and transitions with the intention of securing TrueNorth’s future as a legacy company and broker of choice.    

“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. Robynn originally joined TrueNorth in 2006 and positively impacted the firm and transportation industry through volunteer and association engagements.  

“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 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 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 am proud to be a contributor to TrueNorth’s mission, exploring new heights as an executive member of the TrueNorth team.”  



TrueNorth® Companies, L.C. is a risk management and insurance brokerage firm focused on creating value for our clients, colleagues and communities.  The organization is designed to maintain its closely held and privately held business model supported by an organic growth and internal perpetuation strategy. TrueNorth is headquartered in the Midwest with offices in Iowa, Illinois and Colorado and colleagues located in over 20 states across the nation. Learn more at 

Media Contact:
Mallory Mohwinkle
(319) 739-1357