Chief of Staff

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 Chief of Staff for HPI serves as a strategic partner and force-multiplier to the President, driving operational rigor, alignment, and execution across the business. The role strengthens HPI’s operating cadence, establishes disciplined processes, and ensures the organization functions with clarity, accountability, and maturity. This includes designing governance structures, aligning priorities across functions, and translating strategy into practical, repeatable ways of working.

The Chief of Staff operates as an individual contributor with significant influence responsibility. Discretion, judgment, and the ability to work effectively with senior leaders are essential.

In this role, you’ll: 

• Build and manage HPI’s operating cadence (leadership team meetings, monthly business reviews, initiative tracking, operating rhythms).
• Develop structured processes and frameworks that replace ad-hoc practices, ensuring reliability, transparency, and consistency.
• Support planning, budgeting, performance tracking, and decision-making with clear templates, data, and routines.
• Drive follow-through on commitments and ensure cross-functional accountability.
• Serve as a trusted advisor and sounding board on priorities, risks, organizational dynamics, and emerging issues.
• Prepare key materials for executive forums, enterprise partners, and the Board.
• Synthesize information and recommend clear, action-oriented paths forward.
• Establish and mature governance structures, including decision rights, escalation paths, and operating protocols.
• Manage cross-functional alignment between HPI and enterprise functions (finance, operations, people, clinical, IT, compliance).
• Support operational reviews, financial cycles, and enterprise reporting obligations.
• Build strong partnerships across HPI functions and corporate teams to ensure seamless execution.
• Anticipate interdependencies across initiatives and proactively address barriers.
• Facilitate communication and alignment between the President, leadership team, and broader organization.
• Prepare materials for Board updates, ensuring accuracy, clarity, and consistency.
• Manage key follow-ups and support the President in maintaining effective communication with senior stakeholders.

What you bring

• 10+ years in business operations, strategy, consulting, Chief of Staff, or equivalent roles.
• Demonstrated experience establishing scalable processes and governance structures in a complex or growth-oriented environment.
• Strong analytical and problem-solving capabilities; able to design frameworks and operating mechanisms.
• Exceptional communication and influence skills; able to lead through credibility rather than position.
• Experience working directly with senior executives and boards.
• Background in process improvement (Lean, Six Sigma) preferred. 

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 P