Senior Vice President, Insurance Services

Job Description

Job Level: E7

The SVP of Insurance Services will lead the strategic direction, growth, and operational excellence of our insurance & benefit offerings, which are integrated with our payroll and HR technology platform. This executive will be responsible for driving revenue, deepening client relationships, and ensuring compliance across all insurance & benefit products, including workers' compensation, health benefits, liability, voluntary offerings, and benefit technology services.

• Develop and execute the insurance & benefit services strategy aligned with company goals and client needs.
• Identify market trends and opportunities to expand insurance & benefit offerings within the payroll and HR ecosystem.
• Collaborate with executive leadership to integrate insurance & benefit solutions into broader platform capabilities.
• Oversee the hiring and development of current and new personnel to achieve organizational objectives.

• Lead and mentor a high‑performing sales team focused on insurance & benefit products.
• Partner with payroll and HR sales teams to deliver bundled solutions that drive client value.
• Build and maintain relationships with brokers, carriers, and strategic partners.

• Oversee the development and delivery of insurance & benefit products, ensuring seamless integration with payroll and HR systems.
• Ensure operational efficiency, scalability, and compliance with regulatory requirements.
• Manage carrier relationships and negotiate favorable terms and commissions.

• Ensure all insurance & benefit offerings meet federal and state regulatory standards.
• Collaborate with legal and compliance teams to manage risk and maintain licensing requirements.

• Set and monitor KPIs for insurance & benefit services revenue, client retention, and cross‑sell success.
• Drive innovation in product design, pricing models, and service delivery.

• Bachelor's degree required; MBA or relevant advanced degree preferred.
• 10+ years of experience in insurance services, with at least 5 years in a senior leadership role.
• Proven success in selling and managing insurance products within a technology‑enabled environment.
• Deep understanding of payroll, HR platforms, and how insurance integrates with these services.
• Strong leadership, negotiation, and strategic planning skills.
• Active insurance licenses (e.g., Life, Health, Property & Casualty) preferred.

Agency and brokerage oversight experience preferred. Evidence of passing previous licensing requirements normal and customary with selling and distributing insurance and benefits products.

Guides and inspires others to work with abstract ideas or situations across functional areas of the business. Sets strategy and guides senior leaders in identifying and evaluating fundamental issues and direction for business unit(s). Requires in‑depth knowledge of the business unit, business strategies, and the company's goals.

Interacts internally and externally with executive and C‑Level level management, requiring negotiation of extremely critical matters. Influences policy making.

Directs and controls the activities of one or more business unit, division, product groups or service areas through senior leaders who have overall responsibility for the successful operation of those assigned areas. Clear expertise as a leader and operator.

Typically requires a Bachelor's degree and 15+ years of direct experience, with 10+ years of leadership experience. May require advanced degree.

Sets direction, strategy, and vision for business unit(s). Holds senior leaders accountable for results. Helps shape, exemplify, and hold senior leaders accountable to the management standards of the company. Approves corporate and/or organizational policies and authorizes their implementation. Inspires senior leaders to develop innovative concepts and promote new ideas. Drives meaningful impact and improvements across multiple functions or…