The Opportunity

The Sr. Captive Account Executive delivers captive management and advisory services to Capterra’s clients. This role requires a blend of underwriting and risk management expertise, financial oversight, and relationship leadership, with the ability to act as the central coordinator across internal teams and external partners. Serving as a trusted, strategic resource to boards, owners, and senior stakeholders, the Account Executive manages the day‑to‑day execution of captive programs while ensuring governance, regulatory obligations, and financial activities are addressed in a manner that supports each client’s broader risk and business objectives. As a key member of the Capterra team, this position is critical to delivering a high‑touch, consultative experience to a sophisticated and demanding client base.

Capterra Risk supports a flexible work environment. This role may be performed remotely for candidates with demonstrated experience. Periodic travel for client meetings, board meetings, and other business needs is expected regardless of location. Capterra Risk offers a competitive compensation package which includes salary, paid time off, insurance, 401k and opportunities for bonus earning potential.

To submit your resume, please email jobs@capterrarisk.com.

Key Responsibilities:

Captive Management and Client Advisory:

• Provide strategic advisory support to captive clients by evaluating program performance, captive structure, underwriting results, and long‑term objectives, and translating analysis into clear recommendations.
• Assess client programs on an ongoing basis to identify evolving risk exposures, underwriting considerations, operational needs, and opportunities to enhance captive performance and efficiency.
• Manage the day‑to‑day administration of captive programs, ensuring ongoing alignment with governing documents, operating agreements, bylaws, approved business plans, and contractual service arrangements.
• Apply underwriting and risk management expertise to evaluate client exposures, review premium drivers, analyze rating frameworks, and support the development of underwriting analyses for captive programs.
• Coordinate loss experience reporting by collaborating with claims administrators and supporting claims or risk committees as needed.
• Monitor underwriting outcomes, claims trends, reserve adequacy, and overall financial performance in partnership with actuaries and claims professionals.
• Help lead the coordination of business plans, pro formas, underwriting analyses, and supporting documentation required for domicile submissions or captive program changes.
• Serve as the primary liaison between clients, external partners, and professional advisors—including carriers, reinsurers, brokers, TPAs, auditors, actuaries, legal, tax, and regulatory contacts—coordinating communications, responding to inquiries, and supporting compliance obligations.
• Research and respond to requests from clients and related professionals through written correspondence, phone discussions, and in‑person meetings, addressing complex technical and operational questions.
• Prepare reports, presentations, and special projects that may require data gathering, coordination across parties, document drafting, and distribution to stakeholders.
• Mentor and support junior captive professionals by sharing technical knowledge, providing guidance on captive operations, and contributing to team development.

New Captive Formations, Growth & Business Development Support:

• Take a proactive, solutions‑oriented approach to identifying new captive opportunities by leveraging market insights, industry trends, and strategic relationships to create meaningful, warm introductions.
• Own opportunities through the full lifecycle—from initial relationship development and strategic discussion through coordination of internal teams and successful execution to close.
• Support new captive formations, restructurings, expansions, and run-off of programs through technical expertise and client-facing presentations.
• Participate in prospect meetings, proposal development, and presentations related to captive solutions and outreach.
• Leverage professional networks and industry relationships to help identify and introduce potential new captive clients.

Experience Required:

• Bachelor’s degree in business, finance, accounting, risk management, insurance, or a related field.
• 6+ years of professional experience supporting captive insurance programs, commercial insurance, or complex risk management structures, with exposure to underwriting concepts.
• Background in property and casualty insurance, underwriting, or risk management gained through work with an insurance carrier, brokerage, or captive management environment.
• Knowledge of captive insurance operations, governance, and domicile requirements.
• Strong written and verbal communication skills, with the ability to communicate clearly and professionally with clients, boards, and advisors.
• Highly organized with a strong attention to detail and the ability to manage multiple priorities and deadlines.
• Solid financial skills, including the ability to understand underwriting results, actuarial summaries, and financial reports.
• Advanced proficiency with Microsoft Word, Excel, and PowerPoint, and comfort preparing client‑ready documents and presentations.
• Experience coordinating with external professionals such as actuaries, auditors, tax advisors, attorneys, brokers, and service providers.
• Able to work independently, manage longer‑term projects, and balance strategic initiatives with day‑to‑day responsibilities.
• Periodic travel for client meetings, board meetings, and domicile visits.

About Capterra Risk Solutions

Capterra Risk is a boutique insurance consulting firm that offers an unparalleled level of risk management and underwriting expertise to firms desiring to expand insurance coverage, control losses, harness profits, and preserve assets through captive insurance solutions.

We are an engaged team that works closely to serve our customers with excellence. We have big growth plans; we welcome candidates who want to help lead our expansion.

To submit your resume, please email jobs@capterrarisk.com.

More information about the company can be found at www.CapterraRisk.com.