Director, Total Rewards

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

About the Role

OpenLoop is looking for a Director, Total Rewards to run the compensation, benefits, and equity programs that support our fast-growing workforce. This is a hands-on build-and-run role: you’ll own the day-to-day of our total rewards programs while designing the frameworks that will carry OpenLoop and our family of companies through the next stage of growth, making sure our programs are competitive, fair, and easy to understand.

What You’ll Do

• Own OpenLoop’s compensation programs end to end: job architecture, leveling, salary ranges, market pricing, and offer guidelines.

• Take full ownership of the annual and off-cycle compensation cycles, including budget modeling, calibration support, manager tools, and enablement.

• Advise recruiters and leaders on offers and pay decisions with clear, data-backed recommendations.

• Administer OpenLoop’s equity program, including new-hire, promotion, and refresh grant guidelines, and partner with Legal and Finance on equity pool sizing, and burn rate and dilution modeling.

• Help employees and candidates understand the value of their total rewards package, including equity, through clear education and communication.

• Own benefits strategy and operations: medical, dental, vision, 401(k), leave, and wellbeing programs.

• Lead annual renewals and open enrolment with our broker and carriers, balancing employee experience with cost.

• Manage benefits and rewards vendors, including contracts, performance, and escalations.

• Manage benefits compliance, including ERISA, ACA, COBRA, HIPAA, Form 5500, and nondiscrimination testing.

• Own compensation and benefits integration for acquisitions and harmonize pay and benefits across OpenLoop’s subsidiaries and pharmacy network.

• Lead pay equity analyses, and partner with HR business partners and Legal on FLSA exemption reviews and compliance with multi-state pay transparency and wage-and-hour laws.

• Build reporting on compensation spend, market competitiveness, benefits utilization, and retention risk, turn findings into clear recommendations for leadership.

• Use systems, survey data, AI and automation to make rewards processes faster and more accurate

• Manage and develop the Total Rewards team.

Who You Are

• Experience leading total rewards across both compensation and benefits pillars at high-growth companies.

• A track record of leading and developing team members.

• Experience owning annual comp cycles and building or evolving job architecture, leveling and salary structures.

• Experience administering private-company equity.

• Working knowledge of benefits and pay compliance: ERISA, ACA, COBRA, HIPAA, FLSA, and state pay transparency laws.

• Strong modeling skills in Excel or Google Sheets, plus experience with compensation survey data (e.g., Radford, Mercer, Pave, or comparable).

• Effective communicator who can explain trade-offs to partners, leaders, and make complex programs clear for employees.

Preferred Qualifications

• Total rewards experience in healthcare, telehealth, pharmacy or patient care settings.

• Experience integrating compensation and benefits after acquisitions.

• Experience with Rippling, Workday, Ashby, Carta, Pave or similar platforms.

• CCP, CBP or CECP certification.

• Experience using AI tools to automate compensation and benefits workflows.

Our Benefits

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans

• Flexible Spending/Health Savings Accounts

• Flexible PTO

• 401(k) + Company Match

• Life Insurance, Pet insurance, and more

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.