Director of Transportation Underwriting (REMOTE)

Superior Insurance Partners LLC•Chicago, IL

3d•Remote

About The Position

Superior Insurance Partners is a rapidly growing insurance brokerage platform, focused primarily on providing commercial lines, personal lines, and employee benefit solutions to companies and individuals. Superior acquires and partners with leading independent insurance agencies primarily in the Midwest and Eastern US. The company’s mission is to improve the lives of its agency partners. Superior does this by creating a highly tailored plan for each of its agency partners to help them achieve their goals, and providing customized resources including accounting/finance, recruiting, HR, AMS/IT, marketing, and M&A support. Agency partners are aligned through long-term economic incentives while leveraging the benefits of best practices, scale, and resources across Superior’s shared platform. Superior is backed by Tyree & D'Angelo Partners (“TDP”), a leading Chicago-based private equity firm that makes control ownership investments in, and partners with, lower middle market businesses with the goal of creating meaningful value for all involved. TDP is currently investing out of its third fund and has managed and created over $3 billion of capital and company enterprise value. TDP has significant experience investing in service businesses and has completed over 1000 investment partnerships in its history. Director of Transportation Underwriter Seren Specialty Insurance (SEREN) is a boutique program management and insurtech company delivering specialized insurance solutions across the specialty liability market. SEREN provides end-to-end underwriting, claims management, risk management, and distribution services, enabling efficient deployment of capital for our owned and contracted carrier partners. We are seeking a Director of Transportation Underwriter to join our growing team. This role is designed for a seasoned underwriting professional with deep transportation expertise who can operate with autonomy, influence agency partners, and contribute strategically to portfolio performance. Prior experience on the carrier or MGA/program side is strongly preferred. 100% Remote – flexible, collaborative environment. Role Overview The Director of Transportation Underwriter will be guiding risk selection and driving profitable growth. This individual will serve as a trusted partner to agencies and internal stakeholders while helping shape underwriting strategy, appetite, and best practices.

Requirements

7–12+ years of progressive Trucking / Transportation underwriting experience.
Demonstrated success underwriting complex transportation risks within an MGA, program, or carrier environment.
Strong working knowledge of state and federal trucking regulations (FMCSA, DOT, compliance requirements).
Proven ability to manage portfolio performance and make sound underwriting decisions independently.
Exceptional communication, relationship-building, and negotiation skills.
Comfortable operating in a remote, high-accountability environment.
Willingness to travel occasionally for industry and partner events.

Nice To Haves

Prior experience on the carrier or MGA/program side is strongly preferred.

Responsibilities

Own the full underwriting lifecycle for transportation risks, including submission review, risk analysis, pricing, quote issuance, binding, endorsements, renewals, and compliance with state and federal filings.
Exercise independent underwriting judgment and authority on complex transportation and trucking accounts.
Manage and grow a profitable transportation portfolio, balancing rate adequacy, retention, and loss performance.
Serve as a senior point of contact for agency partners, providing consultative underwriting guidance and market insight.
Collaborate with leadership to refine underwriting guidelines, appetite, and pricing strategies for transportation programs.
Partner cross-functionally with claims, risk management, compliance, and operations to ensure best-in-class policyholder outcomes.
Support business development efforts by evaluating new opportunities, agency relationships, and program enhancements.
Mentor junior underwriting staff as needed and contribute to process improvements and underwriting best practices.
Maintain proactive, high-touch communication with agency partners and internal leadership.
Act as a strategic underwriting resource, helping agencies structure risks for long-term success.
Represent SEREN at industry events, carrier meetings, and key partner engagements as appropriate.