Managing Director

Head of Agency / General Manager – Insurance Division

Location: Phoenix, AZ

Reason for Opening: Replacement

This organization is an established technology‑driven platform serving the transportation and logistics sector. As part of its next stage of growth, the company is expanding into the commercial insurance market with a focus on simplifying and digitizing insurance solutions for trucking businesses, small fleets, and independent owner‑operators.

The insurance division aims to modernize a historically fragmented market by leveraging technology, strong customer engagement, and operational efficiency to deliver a streamlined and intuitive insurance experience.

The Head of Agency / General Manager will lead the strategic growth, operational performance, and market expansion of the company’s insurance division. This individual will be responsible for building a top‑tier distribution strategy, scaling the insurance platform, developing new revenue channels, and positioning the division as a comprehensive insurance solution for customers.

This leader will work directly with the CEO and will have direct access to company resources, support, and decision‑making authority to remove barriers and accelerate growth.

• Drive overall growth and profitability of the insurance division, including strategic planning and financial oversight.
• Develop and execute a competitive go‑to‑market strategy targeting a fragmented commercial trucking insurance sector.
• Lead product and platform initiatives that digitize and simplify the insurance process for both customers and agents.
• Build and manage key relationships with agents, underwriters, carriers, and additional ecosystem partners.
• Establish and execute three primary market‑entry strategies to expand distribution and customer reach.
• Simplify complex insurance workflows by improving communication between systems, teams, and external partners.
• Analyze industry trends, competitive forces, and customer needs to evolve the insurance offering.
• Oversee P&L and ensure the division meets revenue, margin, and growth targets.
• Collaborate with internal teams such as product, marketing, engineering, and operations to ensure alignment with organizational goals.
• Lead, mentor, and develop a high‑performing team, fostering a culture of innovation, accountability, and customer focus.

• Extensive experience in the commercial trucking insurance sector, particularly in distribution, partnerships, or M&A.
• Deep understanding of the small‑fleet and owner‑operator segments.
• Proven success driving growth in a competitive insurance environment.
• Experience working with or building digital insurance platforms or insurtech solutions.
• Strong leadership capabilities with demonstrated experience leading multi‑disciplinary teams.
• Financial acumen with a track record of P&L ownership and profitable growth.
• Strong communication and relationship‑management skills across multiple stakeholders.
• Strategic mindset with the ability to identify opportunities for innovation and differentiation.

• Experience launching or scaling insurance products in the transportation or trucking industry.
• Demonstrated ability to simplify complex policy structures, workflows, and underwriting processes.

This role offers the opportunity to work closely with the CEO, with significant autonomy and organizational backing. The selected leader will have the resources needed to build, grow, and optimize the insurance business with minimal operational roadblocks.