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OpenLoop is a telehealth platform co-founded by Dr. Jon Lensing and Christian Williams, delivering virtual care solutions across all 50 states. The company is scaling rapidly and seeking a Director of Total Rewards to lead compensation, benefits, and equity programs.
In this hands-on build-and-run role, you will own end-to-end total rewards strategy and operations. Key responsibilities include:
**Compensation & Equity:**
- Design and manage job architecture, leveling, salary ranges, and market pricing
- Run annual and off-cycle compensation programs with budget modeling and calibration support
- Administer private-company equity programs (new-hire, promotion, refresh grants) in partnership with Legal
- Partner with Legal and Finance on equity pool sizing, burn rate, dilution modeling, and strategy
- Educate employees on equity value and ownership
- Lead pay equity analyses and ensure compliance with FLSA, multi-state pay transparency, and wage-and-hour laws
- Advise recruiters on offers and pay decisions with data-backed recommendations
**Benefits & Compliance:**
- Own benefits strategy and operations: medical, dental, vision, 401(k), leave, and wellbeing programs
- Lead annual renewals and open enrollment with brokers and carriers
- Manage compliance with ERISA, ACA, COBRA, HIPAA, Form 5500, and nondiscrimination testing
- Manage vendor relationships, contracts, and performance
**Integration & Scaling:**
- Harmonize compensation and benefits across OpenLoop's subsidiaries
- Support diligence and integration for future acquisitions
- Build reporting on compensation spend, market competitiveness, benefits utilization, and retention risk
- Leverage systems, survey data, and AI/automation tools to improve efficiency
You will report to the VP, People Operations & Total Rewards and lead and grow the Total Rewards team as the company scales. The role requires core collaboration hours in Central Time.
**Requirements:**
- Total rewards leadership experience owning both compensation and benefits
- Experience in a high-growth company
- Track record 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 Excel or Google Sheets modeling skills and experience with compensation survey data (Radford, Mercer, Pave, or comparable)
- Clear communicator who can explain trade-offs and simplify complex programs 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 post-acquisition
- Experience with Rippling, Workday, Ashby, Carta, and Pave (or similar HRIS, ATS, equity, and compensation platforms)
- CCP, CBP, or CECP certification
- Experience using AI tools to automate compensation and benefits workflows
