Vice President, Total Rewards and Technology

Job Description:

Cityblock Health is seeking a strategic, experienced, and execution-focused Vice President of Total Rewards and Technology to lead the design and delivery of our total rewards philosophy, HR technology ecosystem, people analytics, and organizational design. This role sits at the intersection of people, performance, and innovation—empowering a high-growth, mission-driven organization to scale with clarity, equity, and operational excellence.

As a member of the People senior leadership team, this executive will collaborate closely with our Finance, Legal, and senior business leaders to align total rewards and people systems with Cityblock’s long-term growth and profitability goals. This is a highly visible role that demands deep functional expertise and a passion for creating impactful, data-driven solutions that shape the future of work at Cityblock.

Key Responsibilities

• Lead Total Rewards Strategy:
  Develop and execute a competitive, scalable total rewards strategy that aligns with our values and business goals—including compensation, equity, benefits, and retention programs.
   

• Compensation & Equity Design:
  Own the development of merit-based compensation models, job-leveling frameworks, and pay-for-performance systems. Partner with Finance andLegal on equity program design and administration, with exposure to executive compensation planning (a plus).
   

• Benefits Leadership:
  Design and implement innovative benefits programs, including modeling and launching self-insured health plans and designing competitive 401(k) strategies to support attraction and retention.
   

• HR Technology & Workday Expertise:
  Serve as the company’s Workday expert, responsible for configuration, system optimization, and full ownership of compensation, benefits, and organizational design modules. Drive roadmap planning and lead cross-functional implementations and enhancements.
   

• Organizational Design & Job Architecture:
  Lead the development and continuous improvement of scalable job architecture and leveling frameworks, ensuring clarity, consistency, and career growth opportunities across the organization.
   

• Retention & Incentive Programs:
  Design and implement strategic retention programs tied to performance, market competitiveness, and critical talent segments.
   

• People Analytics & Insights:
  Build and mature our people analytics function, turning data into insights that inform workforce planning, diversity goals, pay equity, and business performance.
   

• Executive & Board Partnership:
  Serve as a strategic advisor to executive leadership and the Board on all matters related to compensation, rewards strategy, and organizational design.

What You Bring

• 12+ years of progressive leadership experience in Total Rewards, HR Technology, or People Operations within high-growth, mission-driven organizations.
  Deep functional expertise in Workday—particularly in compensation, benefits, advanced compensation planning, and organizational design modules.

• Proven success designing and launching self-insured healthcare programs and comprehensive 401(k) strategies.
   

• Strong track record of building merit-based pay programs, retention strategies, and managing complex job leveling and architecture frameworks.
   

• Experience with equity strategy and, ideally, executive compensation design and compliance.
   

• Strong business acumen with the ability to advise, influence, and partner with senior leaders and board members.
   

• Analytical mindset with experience using people data to drive strategic decisions.
   

Excellent communication, leadership, and change management skills.

We take into account an individual’s qualifications, skillset, and experience in determining final salary. This role is eligible for health insurance, life insurance, retirement benefits, participation in the company’s equity program, paid time off, including vacation and sick leave. The actual offer will be at the company’s sole discretion and determined by relevant business considerations, including the final candidate’s qualifications, years of experience, skillset, and geographic location. The expected salary range for this position is: 

Cityblock values diversity as a core tenet of the work we do and the populations we serve. We are an equal opportunity employer, indiscriminate of race, religion, ethnicity, national origin, citizenship, gender, gender identity, sexual orientation, age, veteran status, disability, genetic information, or any other protected characteristic.

We do not accept unsolicited resumes from outside recruiters/placement agencies. Cityblock will not pay fees associated with resumes presented through unsolicited means.