Vice President - People

VP, People 

Job location: Remote - US

Target Start Date: November 2025

About Waymark

Waymark is a mission-driven team of healthcare providers, technologists, and builders working to transform care for people with Medicaid benefits. We partner with communities to deliver technology-enabled, human-centered support that helps patients stay healthy and thrive. We’re designing tools and systems that bring care directly to those who need it most—removing barriers and reimagining what’s possible in Medicaid healthcare delivery.

Our Values

At Waymark, our values are the foundation of how we work, grow, and support one another:

• Bold Builders: We tackle the toughest challenges in care delivery by harnessing the power of community and technology.
• Humble Learners: We seek feedback, embrace diverse perspectives, and welcome challenges to our assumptions.
• Experiment to Improve: We use data to inform decisions and continuously assess our performance.
• Focused Urgency: Our mission drives us to act swiftly and relentlessly in pursuit of meaningful results.

If this resonates with you, we invite you to bring your creativity, energy, and curiosity to Waymark.

About this role

As Vice President of People, you will lead and scale Waymark’s People function, shaping the strategy that enables our team to thrive and our mission to succeed.  

Reporting directly to the CEO and working closely with the Executive Leadership Team, you’ll be a strategic partner to leaders across the organization–building a best-in-class, people-first culture.

You will be accountable for all aspects of People operations, including employee engagement, talent acquisition, performance management, learning and development, and DEI initiatives. Your leadership will help us build inclusive, collaborative teams and ensure every team member feels supported in doing their best work.   

Key Responsibilities

Strategic Leadership & Organizational Design

• Develop and execute a comprehensive people strategy aligned with Waymark’s mission and growth goals
• Serve as a trusted advisor to the CEO and Executive Leadership Team on organizational development, workforce planning, and change management
• Guide the organization through scale, complexity, and transformation—building clarity, resilience, and alignment

Talent Acquisition & Workforce Planning

• Develop, implement and monitor  end-to-end workforce strategy to attract, hire, and retain top talent across a distributed workforce
• Build scalable hiring processes and tools to support rapid growth and expansion into new geographies
• Partner with hiring managers to forecast workforce needs and ensure alignment with business objectives

Performance, Development & Engagement

• Design and implement performance management systems that foster accountability, growth, and continuous feedback
• Lead learning and development initiatives to support career progression and skill-building across all levels
• Champion employee engagement strategies that promote satisfaction, retention, and a sense of purpose

Diversity, Equity & Inclusion

• Architect and lead DEI initiatives that foster a culture of belonging and equitable opportunity
• Embed inclusive practices into hiring, onboarding, development, and leadership pathways
• Monitor and report on DEI metrics to drive transparency and progress

Compensation, Benefits & Compliance

• Develop, implement and monitor compensation strategy, benefits programs, and total rewards to ensure competitiveness and internal equity
• Partner with Finance to support payroll operations and budget planning
• Ensure compliance with employment laws and regulations across all states of operation

People Analytics & Operational Excellence

• Manage the People team budget and leverage HR analytics to inform strategic decisions
• Track key metrics related to hiring, retention, engagement, and performance
• Continuously improve People systems, tools, and processes to support scale and efficiency

Minimum qualifications

• 15+ years of progressive experience in People Operations / Human Resources, spanning benefits administration, employee relations, performance management, recruitment, and training & development; at least 3 years of leadership experience leading and managing a high-performing HR team and People function 
• Proven experience leading People/HR through significant scale including navigating expansion of workforce into new states. 
• Deep knowledge and understanding of employment & HR related compliance obligations and multi-state laws (federal, state, local)
• Demonstrated success in building and sustaining high-functioning and cross-functional teams and serving as a strategic partner to executive leadership
• Strong commitment to diversity, equity, inclusion, and belonging, with experience embedding inclusive practices across hiring, retention, and culture
• Self-starter with a hands-on approach and passion for improving healthcare access for underserved communities 
• Proven expertise in compensation, benefits, and compliance, including designing total rewards strategies, managing payroll in partnership with Finance, and ensuring multi-state employment law compliance
• Excellent interpersonal skills, with an ability to communicate, clearly and effectively, across different business functions, and navigate complex situations with confidence and empathy Experience delivering programs, policies, and HR support for a diverse, distributed workforce, including experience with hourly healthcare workers and technical teams (e.g., software engineers, hourly healthcare team members)
• Highly operational, data-driven mindset with the ability to design scalable processes, guide strategy and use analytics to drive decision-making
• History of rolling up sleeves and thriving in a mission-driven, fast-paced environment with comfort balancing strategic leadership and tactical execution

Salary Range: $180,000 - $231,000.  Compensation will depend on multiple factors, including job location, training, education, and experience.

In addition to salary, we offer a comprehensive benefits package. Here’s what you can expect:

Stock Options: Opportunity to invest in the company’s growth.
Work-from-Home Stipend: A dedicated stipend for your first year to help set up your home office.
Medical, Vision, and Dental Coverage: Comprehensive plans to keep you and your family healthy.
Life Insurance: Basic life insurance to give you peace of mind.
Paid Time Off: 20 vacation days, accrued over the year, plus 11 paid holidays.
Parental Leave: 16 weeks of paid leave for birthing parents after six months of employment, and 8 weeks of bonding leave for non-birthing parents.
Retirement Savings: Access to a 401(k) plan with a company contribution, subject to a vesting schedule.
Commuter Benefits: Convenient options to support your commute needs.
Professional Development Stipend: A dedicated stipend supports professional development and growth.

Offer of employment is contingent upon successful completion of a background check.

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that some of us may be less likely to apply to jobs unless we meet every single qualification. Waymark is dedicated to building a supportive, equal opportunity, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every preferred qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!