Head of Transformation

Guardian Life Insurance • New York, NY

4d • $178,690 - $293,560

About The Position

Guardian’s Digital and Technology (D&T) organization is transforming how it operates by scaling its product operating model, embedding AI-enabled ways of working, and strengthening execution discipline. The Head of Transformation owns the integrated roadmap, workstream sequencing, dependency management, executive visibility, and accountability for outcomes that turn D&T strategy into measurable progress. The role shapes priorities with senior executives, drives tradeoff decisions, holds workstream owners accountable, and builds the capability needed to sustain change at scale.

This enterprise transformation leader translates strategy into practical execution plans, creates structure across complex and ambiguous work, and influences senior leaders to align on decisions, tradeoffs, and barrier removal. The role leads the advancement of the product operating model and AI Engineering and PDLC transformation, connecting priorities across strategy, portfolio, workforce, coaching, architecture, AI, and change readiness. It also establishes transformation governance, operating rhythms, measurement, executive reporting, and value realization, while leading and developing a small team of transformation program and workstream leads.

The position is based primarily in New York, NY, and reports to the Head of Technology Strategy, Transformation & Planning.

Requirements

• Bachelor’s degree required.
• 10–15 years of experience leading enterprise transformation, technology strategy, operating model, product model, or complex cross-functional change programs.
• Experience leading strategic initiatives, developing roadmaps, and driving successful programs across a matrixed enterprise.
• Experience working in a product-led organization, with a strong understanding of product management practices, technology delivery, and agile ways of working.
• Demonstrated ability to move from ambiguity to clarity by shaping work, defining plans, prioritizing activities, establishing management routines, and driving measurable enterprise impact.
• Strong executive influence and stakeholder management skills, including the ability to advise senior leaders, frame enterprise-wide decisions, resolve cross-functional tension, and drive alignment without direct authority.
• Ability to synthesize complex work into clear narratives, decision materials, operating reviews, and leadership updates.
• Experience building or leading transformation capabilities, including standards for governance, execution discipline, adoption measurement, executive reporting, and value realization.

Nice To Haves

• Advanced degree or equivalent experience.
• Experience with AI-enabled transformation, engineering productivity, or digital/technology operating model change.
• Experience in management consulting, internal strategy, a transformation office, enterprise program leadership, or technology operating model transformation.

Responsibilities

• Own the integrated transformation roadmap across D&T priority workstreams, including sequencing, milestones, interdependencies, risks, executive decision points, and outcome accountability.
• Establish and manage the transformation operating rhythm, including workstream cadences, leadership forums, escalation paths, performance metrics, and mechanisms to remove blockers quickly.
• Advance the product operating model in partnership with the coaching center of excellence and business and technology leaders, driving adoption and measurable maturity.
• Drive the AI Engineering and PDLC transformation program with Engineering Enablement, translating pilot learnings into scaled practices, adoption metrics, and sustained behavior change.
• Connect transformation priorities across strategy, portfolio, workforce, coaching, architecture, AI, and change readiness into a coherent transformation.
• Partner with Strategy and Change leaders to establish stakeholder plans, readiness approaches, communications paths, and adoption measurement for each workstream.
• Build executive visibility into progress through clear metrics, decision materials, operating reviews, fact-based leadership updates, and recommendations that enable timely senior-level decisions.
• Lead and develop a small team of transformation program and workstream leads who structure work, build plans, manage blockers, drive outcomes, and strengthen transformation capability across D&T.

Benefits

• Skill-building and leadership development opportunities.
• Philanthropic opportunities.
• Contemporary, supportive, flexible, and inclusive benefits and resources for eligible full-time employees.
• May be eligible for annual, sales, or other incentive compensation in addition to salary.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior