Senior Director, Stop Loss and Funding Ops

Do you envision working for a company that has the expertise of a long-standing industry leader, but the spirit of an entrepreneur? Does the thought of making a real impact motivate and energize you? If so, HPI is the place for you. Join a team that values integrity, flexibility, loyalty, compassion and dedication—we can’t wait to meet you.

What we do

HPI is unique. A respected industry leader that’s been serving customers for over 44 years, we’re known for our innovation and adaptability. Our experience has given us our expertise, but our forward-thinking, entrepreneurial spirit has given us our strong reputation. As a third-party administrator, we offer a suite of health and benefit solutions to employers. By joining HPI, you’ll contribute to ideas that make a real difference for employers and employees nationwide. There isn’t a challenge we won’t accept and we’re looking for people who have a passion to take it on. Not just a job—a mission.

Our commitment extends beyond our clients to our own employees. We foster a supportive and inclusive work environment where innovation thrives. By investing in our team’s growth and well-being, we ensure they are equipped to provide exceptional service. 

What you’ll do

The Senior Director, Stop Loss & Funding Operations leads the end-to-end operational administration of medical stop-loss coverage, client claim funding, and premium funding for the organization’s self-funded clients. This leader has direct people-leadership accountability for assigned employees and provides functional leadership to an extended team of cross-functional partners who contribute to stop-loss and funding outcomes.

In this role, you’ll also: 

• Lead the end-to-end administration of stop-loss programs, including implementation, policy administration, reimbursement management, renewals, run-out, and terminations.
• Ensure operational processes, policies, systems, and controls are aligned with stop-loss contract provisions, plan documents, eligibility requirements, and reimbursement terms.
• Provide oversight of high-cost claimant identification, reimbursement submissions, recovery efforts, carrier communications, appeals, and operational compliance.
• Manage carrier and stop-loss vendor relationships, including performance monitoring, audits, issue resolution, and operational effectiveness.
• Develop operational reporting, performance metrics, dashboards, and quality initiatives to improve reimbursement recovery, service delivery, and operational efficiency.
• Serve as the senior escalation point for complex reimbursement issues, contractual interpretations, audit findings, and client-impacting operational concerns.

Client Claim-Funding & Premium Administration

• Direct operational processes supporting client claim funding, including funding calculations, cash calls, prefunding requirements, reconciliation activities, and exception management.
• Ensure accurate and timely reconciliation of client funding, paid claims, stop-loss reimbursements, refunds, and outstanding balances in partnership with Finance and Claims.
• Oversee premium-funding operations, including premium calculations, invoicing, collections, reconciliations, remittance coordination, and delinquency management.
• Establish and maintain strong financial controls, reporting processes, audit trails, and documentation standards that support contractual, regulatory, and business requirements.
• Monitor and communicate financial risks, unresolved variances, funding gaps, and operational exposures to leadership and key stakeholders.

People Leadership & Organizational Development

• Lead, develop, and mentor managers and team members through effective coaching, performance management, goal setting, and professional development.
• Build organizational capability through workforce planning, succession planning, cross-training, onboarding, and talent development initiatives.
• Establish clear governance, service expectations, accountability measures, and escalation protocols across direct and cross-functional teams.
• Foster a culture of collaboration, ownership, operational excellence, innovation, and continuous improvement.

Cross-Functional Partnership & Strategic Initiatives

• Partner with Product, Claims, Clinical, Finance, Technology, Client Management, and Data teams to support operational readiness, process improvements, and new product capabilities.
• Translate business and carrier requirements into scalable operational workflows, procedures, system enhancements, training materials, and reporting solutions.
• Drive modernization and automation initiatives that improve efficiency, reduce risk, enhance reporting, and strengthen the client experience.
• Support client-facing teams by providing operational expertise, reimbursement updates, issue resolution, and analytical insights.

Required Qualifications

• Bachelor's degree in Business, Healthcare Administration, Finance, Insurance, or a related field, or an equivalent combination of education and experience.
• 10+ years of progressive leadership experience in stop-loss administration, self-funded health plans, claims operations, funding operations, or a related healthcare/insurance environment.
• 5+ years of experience leading managers and operational teams, including responsibility for employee development, performance management, workforce planning, and cross-functional collaboration.
• Strong knowledge of stop-loss administration, reimbursement processes, policy and contract interpretation, high-dollar claims, and carrier requirements.
• Proven ability to improve operational performance through process optimization, controls, automation, and risk management.
• Exceptional analytical, problem-solving, communication, and stakeholder management skills, with the ability to influence decisions and lead through complexity.

Leadership Responsibilities

• Lead, develop, and mentor managers and team members in a high-performing, service-oriented environment.
• Establish clear goals, performance expectations, and accountability measures across the organization.
• Drive workforce planning, succession planning, talent development, and organizational effectiveness initiatives.
• Foster a culture of collaboration, continuous improvement, customer focus, and operational excellence.
• Partner effectively with senior leadership and cross-functional teams to achieve strategic and operational objectives.

Why choose us?

• We’re a people-first company and value giving back to our community. Ask us about our volunteer opportunities.
• Our space is a reflection of who we are—innovative, open and collaborative.
• We think feeling your best is an important factor in producing great work, so we embrace a “smart casual” dress code and work at ergonomic desks. 
• Need to reenergize? When at our Westborough headquarters, take a break to chat in the onsite café, go for a walk on one of the beautiful trails in our office park, or get in a quick workout at one of the campus gyms. 

Our Benefits Package

We care about you and believe the greatest gift you can give yourself, your family, and the world is a healthy you! We offer a comprehensive and competitive benefits package to help you lead a happy, healthy life, including:

• Medical, Dental and Vision and Prescription Drug Coverage
• Fitness Reimbursement Benefit
• Employee Assistance Program
• Flexible Spending Account & Health Savings Account
• 401(k) and Quarterly Bonuses
• Generous Paid-Time Off & Volunteering Opportunities
• Educational Assistance & Professional Development Opportunities

So, think you want to join the HPI team? We hope to hear from you!

You can read more about us at hpitpa.com/about-us/careers/

EEO/AA/M/F/Vet/Disability Employer