Head of AI-Driven Workforce Transformation

Cityblock; Northern (KY); Hybrid; USD 125,000 - 165,000; Full time

Benefits offered by this job

Health insurance

Retirement benefits

Equity program

Paid time off

Vacation & sick leave

Job summary

Cityblock is seeking a Principal, Workforce Innovation to lead the enterprise-wide future of work and AI-enabled talent optimization. You will partner with People Leadership to design roles, teams, and functions across Cityblock, deciding what should stay human, what to automate, and what to buy or borrow.

You will build a 12–36 month plan, measure ROI, and drive AI-powered workflows and copilots that improve efficiency and decision quality across the People function.

Qualifications

• 8–10+ years in workforce planning, organizational design, or related operating model changes.
• Experience building AI agents, copilots, or workflow automations with measurable impact.
• Ability to manage multi-workstream roadmaps and communicate ROI to executives.

Responsibilities

• Develop a rolling 12–36 month plan for evolving roles, teams, and functions.
• Evaluate options for keeping, borrowing, buying, or building capabilities with AI/automation.
• Design future state for enterprise roles with a human-in-the-loop model and clear ownership.
• Build analytical foundations with task-level breakdowns for cost and time.
• Identify future skills needs and gaps to inform workforce planning and talent strategy.
• Track and report progress on productivity, quality, cost, and retention.

Skills

Workforce planning

Organizational design

Work design

Operations

Process transformation

AI automation

Project management

P&L analytics

Stakeholder management

AI ethics/bias review

Education

Bachelor's degree (Industrial Engineering/Organizational Dev/Human Resources)

Tools

Workday (Skills Cloud)

Data analysis tools

Job description

Cityblock is seeking a Principal, Workforce Innovation to lead the enterprise-wide future of work and AI-enabled talent optimization. You will partner with People Leadership to design roles, teams, and functions across Cityblock, deciding what should stay human, what to automate, and what to buy or borrow.

You will build a 12–36 month plan, measure ROI, and drive AI-powered workflows and copilots that improve efficiency and decision quality across the People function.