Chief Executive Officer
Leadership
Aligning and aspiring to something greater.
Our leaders are guided by a shared commitment to perpetual independence, entrepreneurial spirit and relentless drive to create value as One TrueNorth.
This is our 'true north.'
Executive Leadership
As CEO, Jason leads with vision and purpose, championing innovation, longevity and organizational health. With over 25 years of industry experience, he inspires teams to create lasting value for our clients and within our shared communities, safeguarding our position as a nationally recognized, independent legacy firm.
President & Chief Revenue Officer
Trent drives TrueNorth’s growth strategy with entrepreneurial vision and operational precision. As President & Chief Revenue Officer, he leads enterprise initiatives that align talent, technology and client solutions. His leadership fosters adaptive growth, positioning TrueNorth as a legacy firm committed to innovation, relevance and long-term value creation.
Chief Operations Officer
As Chief Operations Officer, Matt leads enterprise operations with a focus on delivering the TrueNorth Way through exceptional client experiences, strategic innovation and scalable systems. Since joining the firm in 2014, he has leveraged empathetic leadership to foster cohesion across teams, shaping a high-performance culture centered on helping clients and colleagues realize their full potential.
Chief Financial Officer
As CFO, Chad leads with strategic clarity and financial discipline. Since joining the firm in 2008, Chad has championed profitable growth, reinvestment and relevance to ensure TrueNorth remains privately held, forward-focused and committed to delivering innovative solutions that protect and maximize client assets. Chad’s leadership style is defined by a trusted, objective approach and a focus on collaboration, empowering teams to navigate challenges and drive meaningful results.
Executive Vice President, First MainStreet Insurance
Dru Davis leads First MainStreet Insurance, a TrueNorth division committed to growth through M&A, retention and exceptional client experience. As EVP, Dru drives operational excellence across FMSI’s many regional agencies, equipping local firms with shared resources that elevate performance while honoring a community-based service model.
Executive Vice President, Transportation
Chris Gulker oversees TrueNorth’s Transportation Division, the firm’s largest industry vertical. Based in Cedar Rapids, Chris oversees a national team of specialists tasked with creating industry-specific insurance solutions to meet the evolving needs of transportation companies and drivers.
Executive Vice President, Risk Management
Stu Haker leads TrueNorth’s Risk Management Division with deep expertise in enterprise risk planning and alternative risk finance. As EVP, he empowers clients across industries to reduce cost and exposure through strategic programs and proactive solutions that protect assets and elevate organizational resilience.
Vice President of Human Resources
Samantha Hamann leads TrueNorth’s Human Resources function with a focus on colleague well-being, talent development and cultural alignment. Based in Cedar Rapids, she drives strategic initiatives that foster engagement, elevate performance and reinforce TrueNorth’s mission to be a career destination and legacy firm.
Executive Vice President, Employee Benefits
Responsible for TrueNorth’s Benefits and Financial Strategies division, Kyle drives innovation and integrated solutions that address workforce wellbeing, financial stress and healthcare cost containment. Based in West Des Moines, Kyle oversees a national team focused on delivering scalable, data-driven strategies that enhance organizational performance and elevate client experience.
Managing Director
Randall (Randy) Rings serves as Managing Director at TrueNorth, guiding legal strategy and executive leadership initiatives. Formerly Chief Legal Officer, Randy brings deep expertise in corporate counsel and risk advisory. Based in Cedar Rapids, he is charged with advancing TrueNorth’s mission through strategic oversight, mentorship and operational excellence.
Chief of Staff & Chief Information Officer Emeritus
Jeff Sheetz serves as Chief of Staff and CIO Emeritus at TrueNorth, guiding strategic initiatives and enterprise technology. Based in Cedar Rapids, he mentors senior leaders and drives organizational clarity. Jeff’s legacy includes shaping TrueNorth’s entrepreneurial platform and fostering a culture of innovation, collaboration and operational excellence.
Executive Chairman
Duane Smith, Executive Chairman of TrueNorth Companies and Chairman of First MainStreet Insurance, brings decades of visionary leadership to the firm. As TrueNorth’s former President & CEO and one of the firm’s original founders, Duane champions strategic growth, mentorship and community impact — guiding and contributing to TrueNorth’s longstanding legacy of industry leadership.
Chief Commercial Officer
Max Smith serves as Chief Commercial Officer at TrueNorth, where he drives enterprise growth through strategic partnerships, specialty programs and MGA development. Based in Cedar Rapids, Max leads initiatives that expand market reach, foster innovation and position TrueNorth for long-term success in the evolving risk and insurance landscape.
Principal
Bill Teubel brings decades of financial and operational leadership to TrueNorth. Formerly Chief Financial Officer, Bill guides enterprise strategy, cross-functional alignment and long-term planning. Based in Cedar Rapids, his insight and expertise help TrueNorth’s practice areas scale with intention and purpose.
Chief Legal Officer
Robynn Westphal serves as Chief Legal Officer at TrueNorth, overseeing enterprise legal strategy, compliance and risk mitigation. Based in Cedar Rapids, she leads contract governance and supports strategic initiatives across departments. Robynn’s expertise ensures operational integrity and reinforces TrueNorth’s commitment to ethical leadership and long-term organizational resilience.
Executive Vice President, Risk & Workforce Solutions
Bill Zenk serves as EVP of Risk & Workforce Solutions at TrueNorth, leading enterprise-wide strategies that integrate risk mitigation, workforce optimization and client experience. Based in Cedar Rapids, Bill fosters innovation and operational clarity across divisions, empowering teams to deliver meaningful value that enhances client outcomes and contributes to lasting impact.
"Our vision for TrueNorth transcends mere metrics; it acts as our internal compass, embodying the aspirations, beliefs and dreams we hold for our firm. We are the architects of our future, defining the scope of our achievements and the boundaries of what's possible. Let us chart this course together."
Jason Smith
Chief Executive Officer