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 carry OpenLoop and our growing family of companies through the next stage of growth, including harmonizing pay and benefits across subsidiaries and future acquisitions. Throughout, you'll make sure our programs are competitive, fair, and easy to understand.

You’ll report to the VP, People Operations & Total Rewards and lead and grow the Total Rewards team as OpenLoop scales.

What You'll Do

• Own OpenLoop's compensation programs end to end: job architecture, leveling, salary ranges, market pricing, and offer guidelines.
• Run the annual and off-cycle compensation programs, including budget modeling, calibration support, manager tools, and enablement.
• Advise recruiters on offers and pay decisions with clear, data-backed recommendations.
• Administer OpenLoop's equity program, including new-hire, promotion, and refresh grant guidelines in partnership with Legal.
• Partner with Legal and Finance on equity pool sizing, burn rate and dilution modeling, grant guidelines, and strategy.
• Help employees understand the value of their 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 enrollment with our broker and carriers, balancing employee experience with cost.
• Manage benefits compliance, including ERISA, ACA, COBRA, HIPAA, Form 5500, and nondiscrimination testing.
• Manage benefits and rewards vendors, including contracts, performance, and escalations.
• Harmonize compensation structures and benefit plans across OpenLoop's subsidiaries, and support diligence and integration for future acquisitions.
• 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, and turn findings into clear recommendations for leadership.
• Use systems, survey data, and AI and automation tools to make rewards processes faster and more accurate.
• Other Duties As Assigned.

Who You Are

• Total rewards leadership experience owning both compensation and benefits.
• Experience in a high-growth company.
• A track record of building or overhauling job architecture, leveling, and salary structures.
• Hands-on 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).
• Clear communicator who can explain trade-offs to partners and leaders, and make complex programs simple for employees.
• Comfortable working remotely with core collaboration hours in Central Time.

Preferred

• Total rewards experience in healthcare, telehealth, or healthcare services.
• Experience integrating compensation and benefits after an acquisition.
• Experience with Rippling, Workday, Ashby, Carta, and Pave (or similar HRIS, ATS, equity, and compensation planning 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.