Vice President of Total Rewards & People Technology, Cityblock Health
+ Equity program
Healthcare for underserved communities
Be an early applicant
Healthcare for underserved communities
501-1000 employees
Be an early applicant
+ Equity program
501-1000 employees
Company mission
To reduce costs, improve the experience and the quality of care, and transform the health of communities.
Role
Who you are
- 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
- 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
What the job involves
- Cityblock Health is seeking a strategic, experienced, and execution-focused Vice President of Total Rewards and People 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
- Develop and execute a competitive, scalable total rewards strategy that aligns with our values and business goals—including compensation, equity, benefits, and retention programs
- 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)
- 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
- 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
- Lead the development and continuous improvement of scalable job architecture and leveling frameworks, ensuring clarity, consistency, and career growth opportunities across the organization
- Design and implement strategic retention programs tied to performance, market competitiveness, and critical talent segments
- Build and mature our people analytics function, turning data into insights that inform workforce planning, diversity goals, pay equity, and business performance
- Serve as a strategic advisor to executive leadership and the Board on all matters related to compensation, rewards strategy, and organizational design
Our take
Cityblock Health partners with local health insurance providers and professional health practitioners to bring better healthcare to marginalized populations in the US with complex, unmet needs.
While there’s been a groundswell of startups in healthcare, and in particular the value based healthcare space, Cityblock Health sets itself apart through its focus on underserved communities in the US, rather than the wealthy. In doing so, it is helping to drive equity at a time when people need it most.
Its pulled in some serious funding and hasn't wasted a second putting it to work, rolling out its services in new cities and states across the US. And the company's set its sights on reaching 10M members by 2030, and its certainly moving with purpose to get there. Since 2021 funding, its rolled out its community-focused, value-based care model, opening new offices and locking in key partnerships to bring its vision to more people, faster.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
4% employee growth in 12 months
Company
Funding (last 2 of 8 rounds)
Sep 2021
$400m
LATE VC
Mar 2021
$192m
SERIES C
Total funding: $915m
Company benefits
- Employee connectedness - Time to retreat and connect with teammates to shape our culture and set goals together
- Great health insurance - Comprehensive medical, mental health, dental, and vision coverage for employees and their families, including 12 free therapy or psychiatry sessions per year
- Financial savings - 401(k), HSA, FSA, and Commuter benefits to support you now and for the future
- Paid time off - Up to 9 weeks of paid time off, including vacation, sick & safe time, and holidays
- Parental leave - Up to 16 weeks of paid leave for new parents, and a flexible work culture for everyone, including parents
- Learning and development - Access to LinkedIn Learning and weekly professional development classes, with reimbursement for clinical CEUs
Company HQ
Dumbo, NY
Leadership
Toyin Ajayi
(Co-Founder & CEO)Board certified Physician. Served as President of Cityblock in 2017, becoming CEO in 2022. Previously served as Chief Medical Officer at Commonwealth Care Alliance (CCA), as well as Chief Health Officer at Sidewalk Labs.
Share this job
View 6 more jobs at Cityblock Health