Senior Director of Total Rewards

About Us

At SimplePractice, we are improving access to quality care by equipping health and wellness clinicians with all the tools they need to thrive in private practice.

More than 250,000 providers trust SimplePractice to build their business through our industry-leading software with powerful tools that simplify every part of practice management. From admin work to clinical care, our suite of innovative solutions work together to reduce administrative burdenempowering solo and small group practitioners to thrive alongside their clients.

Award-winning and people-first, SimplePractice is shaping the future of health tech. Recognized by MedTech Breakthrough, the Digital Health Awards, and BuiltIn's Best Places to Work.

About the role

We're hiring a Sr. Director of Total Rewards to own compensation, benefits, and people technology end to end, with primary operations across the US and Mexico. You'll set the strategy and do the work designing programs that attract and keep exceptional talent, building the P&C technology roadmap, and leading the People function's AI transformation with human judgment at the center. You sit on the People Leadership Team and partner across every function and the full Executive Leadership Team on the reward decisions that shape the business.

Responsibilities:

• Compensation architecture. Own the 3-year Total Rewards strategy. Maintain a total compensation framework that is competitive, internally equitable, and built to scale including job architecture, pay bands, annual compensation review, and equity. Translate philosophy into policy and manager-ready guidance.
• Variable pay and incentive design. Own and evolve bonus and equity programs tied to performance. Benchmark continuously and make sure programs motivate the right behavior and hold up under scrutiny.
• Benefits. Oversee the design and management of our benefits programs across health, welfare, retirement, and leave. Benchmark continuously and maintain cost-effectiveness and team satisfaction across a multi-country workforce.
• Manager enablement. Equip leaders and managers with the data, framing, tools and education to make great pay decisions and have direct compensation conversations with their teams.
• P&C Technology roadmap and AI transformation. Own the multi-year P&C technology roadmap across Workday, Greenhouse, and adjacent tools. Actively deploy AI across people workflows, compensation benchmarking, pay equity monitoring, band placement modeling, and people analytics with human judgment at the center of every decision.
• People analytics and data foundation. Build the data foundation that enables AI across the People function clean Workday data, integrated systems, governed access, and full auditability. Develop a real-time, action-oriented people analytics capability for HRBPs, managers, and ELT. Own reporting structure and BOD materials.
• Compliance and governance. Ensure rewards programs are administered in compliance with applicable regulations across all geographies. Manage filings, audits, and governance practices. Prepare materials for ELT and Board meetings.
• Team leadership. Lead a high-performing team across comp, benefits, and people technology. Build a strong bench. Evolve performance expectations as AI absorbs execution work and the team shifts toward interpretation and advising.

Desired Skills and Experience:

Experience

• 12+ years in Total Rewards and People Technology, majority in compensation, with growing ownership of people data and HR systems.
• Led a team of 5 or more.
• Designed and managed compensation and equity programs end to end, including executive compensation.
• Deep Workday experience: configuration decisions, data architecture, integrations.
• Multi-geography compensation and benefits experience required. Mexico experience pertaining to IMSS, statutory benefits, labor law strongly preferred.
• Track record presenting at ELT and Board level with the executive presence to take a position and defend it.
• Demonstrated deployment of AI in HR, Compensation, or People Tech workflows compensation intelligence platforms, Workday AI features, predictive analytics, or AI-powered benefits administration.
• Experience evaluating AI vendors, running pilots, and making build-vs-buy decisions for AI tooling in HR.
• Experience redesigning team roles as AI absorbs execution work, including resetting performance standards.
• PE-backed experience is a plus.

Capabilities

• Systems thinker. Compensation, benefits, and HRIS are one system. You manage them that way.
• Analytical precision. You build models others trust and catch data issues before they reach leaders or the BOD.
• Strong communicator. You translate complex compensation and people data decisions into clear, compelling narratives for any audience managers, employees, ELT, or the Board. You present with credibility, take a position, and navigate the conversation with confidence when challenged.
• Change leader. You move a team through AI transformation with honesty, pace, and care for the people involved.
• Operator. You set standards, hold them, and build for scale. You sequence redesign before automation.
• Business judgment. You listen first to leaders, team members, and the market and use what you learn to design programs, processes, and tools that meet real needs. You connect Total Rewards decisions to business outcomes

Benefits

We offer a competitive benefits program including:

• Medical, dental, vision, life & disability insurance
• 401(k) plan with company match
• Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays
• Mental health resources
• Paid parental leave & Backup Care
• Tuition reimbursement
• Employee Resource Groups (ERGs)

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