Director – People Strategy & Optimization

Job Description:

About the Role

Cityblock Health is seeking a Director, People Strategy & Optimization to serve as a trusted advisor and strategic partner within the Office of the Chief People Officer. This person will operate at the center of how the People function plans, communicates, and executes, helping translate strategy into action and ensuring alignment, momentum, and accountability across the organization.

This role spans several critical areas: serving as a strategic thought partner to the People Leadership Team, owning the development of executive level communications, including board and Talent and Compensation materials, using people analytics to surface insights that inform strategy and articulate impact to the business, identifying opportunities to strengthen and evolve how the People function operates, and driving accountability across the PLT and People org against clear, measurable goals.

This role is built for someone who can move fluidly between big-picture strategy and rigorous execution: someone who builds board-ready presentations with polish and precision, crafts brilliant insights leveraging people analytics to inform recommendations and decision-making, and can navigate complex organizational dynamics in service of the function's goals. This is a role for someone who earns trust through consistency and follow-through, not through seeking approval, and who holds themselves and others to a high bar. They are excellent project managers and able to lead independently, while collaborating across teams, influencing without authority.

This is a fully remote role with approximately 2-3 travel engagements for team strategy offsites. Candidates will be needed to work Eastern Time hours.

What You'll Do

• Act as a trusted advisor and thought partner to the People Leadership Team, offering sound judgment on strategic, sensitive, and organizational matters
• Help the People leadership team prioritize effectively, determining what requires broader leadership visibility versus what can be resolved at the team level
• Support continuity and alignment across the People function, including representing key priorities and context in meetings and initiatives as needed
• Build compelling, board- and executive-level presentations and materials, translating complex people data and strategy into clear, decision-ready narratives
• Own the development and preparation of executive-level and org-wide communications, including Board Talent and Compensation Committee materials, partnering with Finance, Legal, and executive stakeholders to ensure materials are accurate, well-framed, and delivered on schedule
• Anticipate questions and prepare supporting analyses and talking points ahead of executive and Board discussions, and track follow-up actions and commitments
• Bring deep fluency in people analytics to inform strategy, clearly articulate impact and ROI to the business, track progress against goals, and surface insights proactively
• Connect information and trends across People disciplines to surface patterns and insights that may not be visible within any single function
• Assess and improve how the People function operates, including priorities, decision-making, and resource allocation, identifying opportunities to strengthen the operating model as Cityblock scales
• Drive high-functioning capabilities across the People Leadership Team and broader People organization
• Build credibility and influence outcomes across teams and functions through expertise, consistency, and clear communication
• Anticipate and help resolve friction points across stakeholder groups in service of the function's goals
• Set and hold the People leadership team accountable both day-to-day and strategically, big picture
• Lead the team to design and deliver against clear, measurable goals, using strong SMART goal-setting and program management discipline
• Manage complex, cross-functional programs and initiatives from strategy through execution, ensuring nothing falls through the cracks
• Deliver clear, direct feedback to peers and team members in service of high performance, comfortable holding a high bar even when it's not the most popular position
• Take direction well and execute independently once aligned, bringing genuine curiosity to new problems and ambiguous situations
• Collaborate closely and lean in as a true partner to the People leadership team, while maintaining the independence to drive work forward without constant oversight

What We're Looking For

• 7+ years of experience in strategic operations, program/project management, management consulting, or a comparable high-accountability strategic role; People/HR-adjacent experience a plus, but not required if analytical and program management skills are strong
• Demonstrated ability to build high-quality, executive- and board-level presentations, with strong command of storytelling through data
• Experience preparing materials for or presenting to a Board of Directors or Compensation Committee, ideally in a People, Finance, or Strategy capacity
• Strong people analytics fluency: comfortable working with workforce data, engagement metrics, and talent metrics to inform strategy and decision-making
• Experience working within Workday (or comparable HRIS platforms) to access, interpret, and present workforce data
• Proven ability to influence without formal authority, and to navigate complex stakeholder dynamics with tact and discretion
• A confident communicator, written and verbal, who can hold a room and hold a hard conversation
• A track record of setting and enforcing accountability, including experience with SMART goal frameworks and performance tracking
• Someone who is comfortable earning trust and respect over time, rather than seeking to be liked in the short term
• Excellent program management skills, with the ability to manage multiple complex workstreams simultaneously
• A naturally curious, collaborative mindset, paired with the independence to execute without close supervision once direction is set

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: 

$165,000 - $175,000

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.