Location: On site or Remote
Position Summary:
Dynamic Specialty Inc. is seeking an experienced and driven Program Manager to lead the development, implementation, and ongoing management of specialized commercial trucking and auto liability insurance programs. This is an opportunity for a seasoned industry professional to bring their expertise, market relationships, and underwriting knowledge to a high-impact role with significant earning potential and operational autonomy. The ideal candidate has spent their career building deep expertise in commercial trucking and auto liability markets — and is ready to leverage that experience in an environment that rewards performance, values industry knowledge, and supports long-term growth.
If you have deep technical expertise, strong market relationships in commercial trucking and auto liability, and are ready for a high-autonomy, high-reward contractor opportunity — this role was built for you. Compensation for this role is structured to reflect the value a top-tier industry professional brings. Base compensation is highly competitive, with significant performance-based earning potential tied directly to program results. The full structure is discussed during the interview process.
Essential Duties / Responsibilities:
- Develop, launch, and manage commercial trucking insurance programs, ensuring profitability, compliance, and long-term sustainability.
- Aggressively pursue and develop commercial trucking and auto liability markets through direct outreach, networking, and leveraging existing industry relationships.
- Serve as the senior underwriting authority on commercial trucking and auto liability programs — capable of attesting to program structures, risk selections, and coverage decisions with full confidence.
- Apply deep technical underwriting expertise to evaluate complex risks, set pricing and terms, and maintain underwriting discipline across all managed programs.
- Collaborate with the underwriting department to develop and integrate technology solutions that enhance underwriting processes, focusing on workflow optimization, risk selection, and underwriting discipline.
- Establish, negotiate, and manage contracts, procedures, and ongoing relationships with carrier partners and MGAs.
- Lead detailed onboarding and ongoing management of carrier relationships and approved insurance programs, ensuring alignment with underwriting appetite and operational standards.
- Collaborate with IT and technology partners on software development and system enhancements related to underwriting workflows, agency integrations, and program management.
- Prepare and deliver monthly underwriting productivity, performance, and forecast reports to the CEO.
- Support the evaluation, onboarding, and stabilization of new programs and carrier opportunities while strengthening and maintaining existing program relationships.
- Collaborate with carrier partners, reinsurers, and underwriting teams to design program structures, pricing models, coverage forms, and underwriting guidelines.
- Coordinate with claims partners to review claims performance, loss control strategies, and claims handling effectiveness to improve overall program results.
- Lead renewal strategies and negotiations with carrier partners and MGAs.
- Support sales and distribution teams by providing underwriting training, technical guidance, and program education to approved agencies.
- Drive brand awareness and market presence by representing the company at approved industry conferences, events, and networking opportunities, with a focus on expanding relationships in trucking and auto liability markets.
- Contribute to agency engagement and attraction efforts by supporting program positioning, underwriting clarity, and operational excellence.
- Participate in training, development, and performance management of the underwriting team in collaboration with company leadership.
Knowledge / Skills / Abilities (KSA’s):
- Underwriting Authority & Technical Expertise — Possesses hands-on underwriting depth in commercial trucking and auto liability sufficient to personally attest to program structures, coverage decisions, and risk selections without oversight. Able to set terms, evaluate complex risks, and defend underwriting rationale to carriers and partners.
- Market Development & Business Generation — Demonstrated ability to identify, pursue, and close new program and market opportunities. Proactively picks up the phone, works existing relationships, and opens new ones to grow the book. Knows the trucking and auto liability market and moves with urgency.
- Carrier & MGA Relationship Management — Deep, established network of carrier, MGA, reinsurer, vendor, and agency relationships in the commercial trucking and specialty insurance space. Able to leverage these connections to bring programs to market and sustain long-term partnerships.
- Program Structuring & Pricing — Skilled in structuring insurance programs from the ground up — including coverage design, pricing models, underwriting guidelines, and reinsurance arrangements — that are profitable, compliant, and sustainable.
- Negotiation — Strong negotiator in carrier contract discussions, MGA agreements, and renewal terms. Able to represent Dynamic Specialty Inc.’s interests effectively while maintaining productive long-term relationships.
- Data Analysis & Performance Reporting — Comfortable using loss ratios, program performance data, market analytics, and financial forecasts to inform decisions, identify risks, and communicate program health to leadership.
- Strategic Thinking — Develops and executes strategies to grow market presence, expand program offerings, and strengthen competitive positioning in the commercial trucking and auto liability space.
- Communication — Speaks and writes clearly and persuasively with carriers, agencies, reinsurers, and internal teams. Capable of delivering executive-level reports and representing the company at industry events with credibility.
- Problem Solving & Initiative — Able to identify program performance issues, underwriting gaps, or market shifts and develop practical, timely solutions without waiting to be directed.
- Ethics & Professionalism — Treats partners, clients, and colleagues with respect; upholds confidentiality; works with integrity; and represents Dynamic Specialty Inc. with professionalism in all interactions.
- Organizational Skills — Manages multiple programs, carrier relationships, and deadlines simultaneously without losing accuracy or momentum.
- Innovation — Brings creativity and resourcefulness to program design, market strategy, and operational challenges. Constantly looks for ways to improve processes and outcomes.
Minimum Qualifications:
Required
- Bachelor’s degree in Business, Finance, Risk Management, Insurance, or a related field, or equivalent relevant experience.
- 15–20 years of progressive experience in specialty commercial insurance, with deep specialization in commercial trucking and auto liability.
- Sufficient underwriting expertise to personally attest to program structures and risk decisions.
- Demonstrated ability to independently underwrite commercial trucking and auto liability risks, including evaluation of fleet size, commodity type, driver qualifications, loss history, and coverage structuring.
- Experience setting and managing underwriting guidelines, appetites, and authority levels within a program or MGA environment, including the ability to read, interpret, and negotiate policy forms, endorsements, and coverage terms specific to commercial auto and trucking liability.
- Working knowledge of reinsurance structures — including quota share, excess of loss, and facultative arrangements — and experience with loss ratio analysis, rate adequacy review, and portfolio management to maintain program profitability.
- Familiarity with DOT regulations, motor carrier filings (MCS-90), and compliance requirements relevant to commercial trucking insurance.
- Proven track record of building and working trucking auto liability markets — established carrier, MGA, vendor, and agency relationships.
- Active Property & Casualty (P&C) insurance license in the applicable state(s), or ability to obtain required licensing within a specified timeframe.
- Ability to work independently as a contractor while collaborating effectively with internal teams.
- Strong organizational skills with the ability to manage multiple programs, priorities, and deadlines.
Preferred
- Advanced underwriting/brokering certifications (e.g., CPCU, AU, ARM, CIC, or similar).
- Prior experience managing captive programs or surplus lines distribution channels.
- Prior experience in a Managing General Agency (MGA) or specialty insurance environment.
- Demonstrated experience working directly with carriers and negotiating underwriting expectations.
- Experience supporting business growth initiatives and market expansion strategies.
- Track record of automating and streamlining processes.
- Proven ability to leverage data in risk analysis and strategic decision making.
Physical Demands and Work Environment:
- Primarily seated, computer-based office role.
- Moderate noise level typical of a professional office environment.
- On-site position or remote if based outside of office area.
- Standard business hours with occasional extended hours to support service demands.
- Travel might be possible for carrier meetings, agency visits, and industry conferences.
License/Certification:
- Property & Casualty insurance license (General Lines 2-20) (Preferred)
Work Location: In person
