Director Workforce Transformation

The Hartford•Columbus, OH

2d•Hybrid

About The Position

We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future. The Director, DAIO Workforce Transformation is a pivotal leadership role responsible for helping to shape and execute the future workforce strategy for the Data, Analytics, AI, and Operations (DAIO) organization. Reporting to the VP, DAIO Strategy & Innovation, this role will lead workforce transformation initiatives that ensure DAIO has the right skills, capacity, and operating model to deliver on its strategy and enable The Hartford’s AI transformation. This leader will help develop and execute multi-year workforce strategies, playing a critical role in how DAIO attracts, develops, and sustains talent to meet future business and technology needs. The role partners closely with DAIO senior leaders, HR, and Technology teams to evolve workforce capabilities, drive future-focused skilling initiatives, assess organizational needs, inform build-versus-buy decisions, and embed AI-powered ways of working across the organization. This role will have a Hybrid work schedule, with the expectation of working in an office (Columbus, OH, Chicago, IL, Hartford, CT or Charlotte, NC) 3 days a week (Tuesday through Thursday).

Requirements

Bachelor's degree in Business, Finance, Strategy, HR, or a related field; MBA or advanced degree preferred
10+ years of leadership experience in workforce strategy, management consulting, transformation, or related roles, preferably within the insurance or financial services industry
Strong technology, analytics, or AI acumen; with strong AI/ML or analytics background preferred
Proven track record driving large-scale transformations with measurable results
Exceptional communication and presentation skills, with the ability to influence at all levels of the organization
Ability to work effectively in fast paced dynamic environment
Strong analytical and problem-solving skills, with a focus on data-driven decision-making
Strong commitment to continuous improvement and professional development
Experience operating effectively in a fast paced, matrixed environment, with cross functional teams
Comfortable navigating ambiguity and driving clarity in dynamic business scenarios
Proven ability to lead and collaborate cross-functional initiatives
Commitment to continuous improvement and innovation
Candidate must be authorized to work in the US without company sponsorship.
The company will not support the STEM OPT I-983 Training Plan endorsement for this position.

Responsibilities

Strategic Planning & Execution: Co-develop and activate the DAIO Workforce Strategy, ensuring alignment with DAIO business priorities and the enterprise AI strategy
Lead multi-year workforce transformation roadmaps, translating strategy into executable initiatives with clear outcomes
Advance & maintain DAIO’s strategic workforce planning (SWP) program, including demand, capacity, and skills forecasting
Partner with DAIO Senior Leadership Team (SLT) to identify sources of demand, critical roles, and capacity constraints
Support ongoing maintenance and evolution of workforce plans to reflect changing business and technology priorities
Establish and monitor KPIs and success metrics to measure workforce transformation impact and ROI
Conduct organization gap assessments
Lead strategic initiatives related to workforce transformation and workforce strategy
Partner with HR, Technology Learning, and DAIO leaders to shape future-focused learning strategies, including AI, analytics, and digital skilling
Coordinate and partner with DAIO SLT to ensure high quality messaging in Senior Executive deliverables
Partner with HR and DAIO SLT to determine talent pipeline strategies
Partner with LPM and Procurement to establish and manage strategic vendor relationships aligned to DAIO objectives
This role may lead a small team supporting workforce strategy and transformation initiatives