Vice President of Insurance

OneDigital

Vice President of Insurance guiding strategy, analytics, and long-term financial performance at OneDigital. Leading a high-performing team to innovate in the evolving PEO insurance market.

Posted 6/11/2026full-timeRemote • 🇺🇸 United StatesLead💰 $200,000 - $250,000 per yearWebsite

About the role

Key responsibilities & impact

Own the enterprise insurance and underwriting strategy, ensuring alignment with organizational goals, workforce strategy, and financial controls.
Play a central role in developing the company’s global insurance and risk-financing strategy, ensuring alignment with operational realities, growth plans, and executive risk appetite.
Establish governance models, controls, and escalation frameworks to ensure payroll accuracy, compliance, and risk mitigation.
Serve as the executive authority on payroll-related matters, including audits, regulatory inquiries, and complex workforce scenarios.
Execute enterprise-level underwriting strategy aligned with company growth, profitability, and risk tolerance goals.
Partner with senior executives to shape underwriting philosophy, pricing models, and long-term portfolio strategy.
Drive innovation and transformation initiatives, including process optimization, automation, and system enhancements.
Ensure underwriting practices support revenue growth while maintaining disciplined risk management.
Lead system implementations, upgrades, integrations, and automation initiatives.
Lead and develop a multidisciplinary organization team members.
Build a culture of accountability, continuous improvement, customer service, and compliance excellence.
Identify opportunities to streamline processes, improve controls, and enhance the employee payroll experience.
Leverage analytics and reporting to monitor performance, identify trends, and drive data-informed decisions.

Requirements

What you’ll need

Bachelor’s degree in business, Human Resources, Finance, Accounting, or a related field required; Master’s degree preferred.
12–15+ years of progressive experience in payroll, HR operations, or related fields, including senior leadership responsibility.
Demonstrated experience leading complex, large-scale environments and managing cross-functional teams.
Deep expertise in insurance and underwriting operations, and compliance.
Strong understanding of insurance operations, data analytics.
Proven executive leadership, change management, and stakeholder influence skills.
High attention to detail balanced with strategic, enterprise-level thinking.
Exceptional problem-solving, analytical, and decision-making capabilities.

Benefits

Comp & perks

health, wellbeing, retirement, and other financial benefits
paid time off
overtime pay for non-exempt employees
robust learning and development programs
reimbursement of job-related expenses

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

insurance strategyunderwriting strategypayroll accuracyrisk managementprocess optimizationautomationdata analyticscompliancefinancial controlsportfolio strategy

Soft Skills

executive leadershipchange managementstakeholder influenceproblem-solvinganalytical skillsdecision-makingattention to detailstrategic thinkingcustomer servicecontinuous improvement

Certifications

Bachelor’s degreeMaster’s degree