Vice President of Insurance - Remote

Are you looking to accelerate your career without having to hide your authentic self - a place where you can be you? A career that’s making a bigger impact on the world? At OneDigital, we are on a mission to help people do their best work and live their best lives. From the services we offer to the way we show up for each other each day, we are fueling dreams, achieving big goals, and embracing each other’s truest selves.

We understand that pursuing a new job is a big deal. Maybe you’re afraid you won’t fit in. Well, here’s the good news. For us, the days of “fit in to get in” are over and being different is not a barrier to getting ahead. Greatness comes in all shapes, sizes, colors, and experience levels. If you are looking for a people-first culture that is wired for growth, driven to serve, and totally committed to having your back, give us a shot. Your best life awaits.

Must be eligible to work in the United States without the need for work visa or residency sponsorship.

Our Newest Opportunity:

The Vice President of Insurance you’ll serve as the company’s senior insurance leader, guiding strategy, analytics, and long-term financial performance across the organization. This role partners closely with executive leadership to support data-driven decision-making related to underwriting, pricing, reserving, reinsurance, exposure, and business scale. You’ll lead and develop a high-performing team while driving innovation through advanced analytics, predictive modeling, and emerging technologies in the evolving PEO insurance market.

Key Responsibilities

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.

Required Experience & Education

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.

Knowledge/Skills/Abilities

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.

Preferred Skills

PEO experience is a plus.

Work Environment

The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. This job is operated in an indoor office environment.

The typical base pay range for this role nationwide is $200,000 to $250,000 per year.

Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company’s performance. We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non-exempt employees, and robust learning and development programs. You will receive reimbursement of job-related expenses per the company policy and may receive employee perks and discounts.

To learn more, visit: www.onedigital.com/careers

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