Senior Director of Talent Optimization & AI

Cityblock Health

29d

About The Position

About the Role The Senior Director of Talent Optimization & AI is a key member of the People Leadership Team and the organization’s primary architect of AI-enabled Talent Strategy. This leader owns Strategic Talent Acquisition, Internal Mobility, AI innovation across the People org, Predictive & Talent Analytics, and Talent Optimization — building the intelligence, systems, and capabilities required for a modern, skills-based and AI-forward workforce. Partnering closely with the CTO and AI/ML teams, this leader embeds AI deeply into how we attract, deploy, develop, and optimize talent. They operate as a customer-obsessed, operationally excellent, P&L-minded business owner, transforming TA into a proactive, predictive, and ROI-driven talent engine while maintaining budget neutrality.

Requirements

10+ years of People/Talent leadership in high-growth or complex environments.
Proven success transforming TA or People capabilities using AI and intelligence platforms.
Deep experience with Workday for recruiting and HRIS, including optimization of the Workday Talent Acquisition, Talent Optimization, and Workforce Planning suites.
Customer obsession and demonstrated operational expertise and rigor.
Experience with skills-based workforce models, Workday Talent Marketplace, predictive analytics, or workforce planning.
Strong understanding of ethical and responsible AI, compliance, and governance.
Demonstrated ability to build and lead teams, influence executives, and operate with a P&L mindset.

Responsibilities

AI-Driven People Strategy & Responsible Innovation Serve as the People organization’s AI leader and strategic partner to CTO/AI teams. Build and govern the roadmap for AI deployment across the People lifecycle — talent intelligence, internal mobility, workforce planning, automation, assessments, and analytics. Leverage Workday’s AI capabilities to govern the roadmap for AI deployment within the function. Evaluate emerging technologies, maintain responsible AI frameworks, and ensure compliance, transparency, and ethical use. Embed AI into workflows to elevate efficiency, accuracy, decision quality, and customer experience for candidates, employees, and managers.
Strategic Talent Acquisition (AI-Enabled, Predictive & Customer-Obsessed) Own and evolve Strategic TA into a predictive, market-intelligent, AI-powered engine that anticipates talent needs and drives future-fit hiring. Leverage Workday Recruiting to manage the end-to-end recruiting life cycle, from workforce planning and sourcing to advanced talent analytics and offer management. Use AI, Workday Skills Cloud, skills intelligence, and market data to forecast capability gaps, identify skill adjacencies, and guide build/buy/borrow decisions. Proactively build, nurture, and manage high-quality talent pipelines for critical, high-value, and future-skill roles using AI-driven sourcing and relationship-based engagement. Drive disciplined build/buy/borrow decisions for open roles, optimizing cost, speed, and long-term capability development. Deliver a white-glove, personalized, and high-touch recruiting experience, leveraging Workday’s integrated candidate engagement and mobile capabilities to elevate candidate satisfaction and strengthen long-term talent relationships across all levels of talent, from Executive to our amazing frontline Cityfolx. Create targeted strategies for competitive or hard-to-fill roles while maintaining budget neutrality. Elevate employer brand through differentiated, data-driven storytelling and precision engagement across digital channels.
Skills Architecture & Internal Mobility Partner with L&D, Org Development, and People Technology to define and maintain a unified skills taxonomy and skills-based workforce model. Strategically implement and evolve the Workday Talent Marketplace and Workday Skills Cloud as the operating model for an AI-enabled internal talent marketplace, matching employees to roles, projects, and development opportunities. Integrate skills intelligence into hiring, development, performance, and mobility to enable a more fluid and adaptive workforce.
Talent Analytics, Predictive Workforce Planning & Optimization Build enterprise capabilities in predictive analytics — workforce forecasting, scenario modeling, supply/demand, and cost/benefit decision support. Utilize Workday People Analytics and Workday Planning to build enterprise capabilities in predictive workforce forecasting, scenario modeling, and cost/benefit decision support. Create dashboards and models that guide talent allocation, organizational design, and workforce investment decisions. Use analytics to improve early-tenure outcomes, reduce new-hire attrition, and strengthen quality-of-hire through predictive onboarding and performance insights. Connect talent decisions to productivity, retention, and business performance to drive continuous improvement across the talent lifecycle.
Operational Excellence & P&L Leadership Operate Strategic TA and Talent Optimization as a business with clear KPIs, dashboards, SLAs, and ROI models. Drive operational rigor, standardization, and continuous improvement across hiring, mobility, and talent intelligence workflows. Own the operational excellence of Workday as the primary system of record across recruiting, workforce planning, and people analytics processes. Maintain strict cost discipline, ensure budget neutrality, and optimize internal/external resource allocation. Improve velocity, quality, efficiency, and predictive accuracy of all talent processes through experimentation, measurement, and data-driven decision-making.
Employer Brand, Candidate Experience & Hiring Excellence Partner with the Employee Experience team to execute employer brand strategy with a focus on differentiation, clarity of value proposition, and market reach. Own the full candidate experience, optimizing the Workday Recruiting module to ensure it is personalized, efficient, equitable, brand-aligned, and operationally excellent. Up-level hiring capabilities across the company through structured interviews, capability rubrics, assessments, AI-guided decision support, and manager enablement.
Leadership & Collaboration Lead and develop a high-performing cross-functional team Collaborate with People Leadership Team peers to integrate insights into L&D, performance, culture, and org design strategies. Build a culture of innovation, responsible risk-taking, customer obsession, and continuous improvement across the People function.