Principal, Workforce Innovation

Job Description:

About the Role

Cityblock Health believes healthcare transformation starts with transforming how we work.

We're looking for an influential Talent Architect and AI expert to lead two connected functions: (1) building for the future of work, evolving our organizational workforce architecture by partnering with every team and function to identify where AI and automation can be integrated into how we work, and partner across the People org to identify where and how to invest in strengthening human capabilities, skills, and competencies; and (2) driving the AI roadmap for the People team, identifying opportunities and building solutions that directly improve how the People team operates in support of the business and our members.

This is a high-impact individual contributor role reporting to the SVP of People Business Partners and Workforce Architecture, and working in very close partnership with the Sr. Director of Talent Optimization and AI.

You are a strategic operator who loves diving deep into analytics and working across every level and function of the business. At the core, this means setting a clear roadmap and orchestrating the cross-functional work with speed and discipline; building AI capabilities and workforce recommendations and driving them to completion, not just proposal; measuring and reporting the P&L and ROI impact of your work, consistently and transparently; communicating clearly and proactively at every level to build trust through consistency; and partnering collaboratively across the organization while holding a high bar for accountability, your own and others'.

What You'll Do

1. Evolve Workforce Architecture for Future of Work

• Systematically evaluate roles across every level and function in the organization to assess where AI or automation can take on existing work, where an AI agent could augment or extend a team's capacity, and where human skills or competencies need to be built or added.

• Partner directly with the Executive Leadership team and business leaders to translate these assessments into concrete workforce architecture recommendations, not abstract frameworks.

• Build a repeatable methodology for this review so it scales across the organization rather than being a one-time audit.

• Shape the organization's workforce strategy by synthesizing ground-level operational data into high-level planning frameworks, advising the SVP on the evolution of our org-wide structure.

2. Drive AI Evolution for the People Organization

• Identify, prioritize, build, and implement AI opportunities across every People function, from Talent Acquisition to Total Rewards to Employee Relations.

• Serve as the strategic AI partner to the Chief People Officer, architecting and integrating high-leverage tools that amplify executive capacity, accelerate decision-making velocity, and scale the impact of the function.

• Design, prototype, and deploy AI-powered workflows, copilots, and agents; build a reusable library of these solutions with documented standards for governance and lifecycle management.

• Partner with Security, Legal, Compliance, and IT to ensure every solution is responsibly and compliantly implemented.

3. Own Delivery, Measurement, and ROI

•  Develop and own clear roadmaps and project plans for all initiatives across both functions, with defined milestones, owners, and timelines.

• Ensure all deployed solutions meet enterprise-grade security and accuracy standards, and measure the impact and ROI of what you ship, connecting AI and workforce investments to real business outcomes, not adoption metrics.

• Build analytics frameworks and executive-ready dashboards that track utilization, efficiency gains, cost impact, and quality improvements.

• Run a disciplined, transparent project management process so stakeholders always know where things stand, what's at risk, and what's needed from them.

4. Drive Cross-Functional Delivery Without Direct Authority

• Work collaboratively acrossPeople Business Partners, Talent Acquisition, Learning & Development, Total Rewards, People Operations, Legal, Compliance, Information Security, Product, Engineering, Data Science, Clinical Operations, and Executive Leadership.

• Influence and align stakeholders across radically different disciplines and seniority levels, from frontline analysts to senior leadership, communicating with equal clarity to each.

• Partner with teams to design solutions and hold the collective effort accountable to actually shipping, not just recommending.

How You Work

• Applied  AI Leadership: you possess a proven track record of architecting, deploying, and scaling production-grade AI agents, copilots, and/or automations, owning the full lifecycle from technical design to verifiable business impact.Analytics and insight-driven: you default to data, and you're comfortable quantifying the ROI and P&L impact of your work.

• Strong project management discipline: you architect, manage, and drive high-stakes initiatives, ensuring that complex, multi-stream strategies are executed with precision, accountability, and measurable results.

• Clear communicator at every level: you adjust tone and depth for a frontline analyst, a functional VP, or executive leadership without losing precision.

• Able to influence without authority: you navigate complex organizational dynamics to align cross-functional leaders on high-stakes, ambiguous initiatives, driving consensus even where perspectives differ.

• High autonomy and ownership: you thrive in high-ambiguity environments, exercising sound judgment to synthesize incomplete data into clear strategic direction and executing with full accountability for outcomes.

• Organized and accountable: you hold yourself and others to commitments and deadlines.

• Fast-moving and collaborative: you prioritize velocity and iterative progress over perfection. You launch, learn, and optimize in lockstep with your stakeholders, ensuring solutions are built with the business to drive seamless adoption and immediate impact.

Qualifications

Required

• 8+ years leading strategic initiatives spanning People/HR, Operations, Consulting, Product, Digital Transformation, or Organizational Effectiveness.

• Demonstrated, hands-on track record of building and shipping AI agents, copilots, workflow automations, or similar intelligent systems  with concrete success stories and measurable outcomes.

• Strong understanding of LLMs, prompt engineering, agent orchestration, and automation platforms.

• Proven project management skills - able to build and run roadmaps and project plans for complex, multi-stakeholder initiatives, and deliver on time.

• Demonstrated ability to measure and communicate P&L impact and ROI for strategic initiatives.

• Experience with workforce planning, organizational design, or job/role architecture work at scale.

• Exceptional communication skills across all levels of an organization, from frontline to C-suite.

• Demonstrated ability to influence without authority and drive accountability across teams you don't manage.

• Advanced analytical skills with experience using data and insight to drive prioritization and decisions.

• High degree of autonomy and ownership; comfortable operating with ambiguity and imperfect information.

Preferred

• Experience in healthcare or other highly regulated industries.

• Experience with Workday, HR technology ecosystems, automation platforms, and enterprise AI tools.

• Experience working alongside engineering and product teams to deliver AI capabilities.

• Prior experience supporting or advising a CPO, CHRO, or other senior executive directly.

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: 

$135,000 - $175,000 Annual

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.