Head of Transformation

Guardian Life

. Own the integrated transformation roadmap across D&T priority workstreams, including sequencing, milestones, interdependencies, risks, executive decision points, and outcome accountability .

Posted 10/23/2026full-timeNew York City • New York • United StatesLead💰 $178,690 - $293,560 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading enterprise transformation initiatives, including technology strategy and product operating models, while effectively managing stakeholder engagement and executive reporting. Proven ability to drive measurable impact through strategic planning, agile methodologies, and AI-enabled transformation.

Highest-signal resume keywords

Enterprise Transformation LeadershipTechnology Strategy DevelopmentStakeholder ManagementAI-Enabled TransformationAgile Methodologies

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Enterprise TransformationTechnology StrategyProduct Management PracticesAgile Ways Of WorkingRoadmap DevelopmentPerformance MetricsGovernanceExecution DisciplineAdoption MeasurementValue Realization

Soft Skills

Executive InfluenceStakeholder EngagementCross-Functional AlignmentNarrative SynthesisLeadership Development

Certifications & Qualifications

Bachelor's DegreeAdvanced Degree Preferred

Industry Keywords

Transformation OfficeManagement ConsultingDigital Operating ModelEngineering ProductivityComplex Change Programs

About the role

Key responsibilities & impact

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
Lead advancement of the product operating model with the coaching center of excellence and business and technology leaders
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
Partner with Strategy and Change leaders on stakeholder plans, readiness, communications, and adoption measurement
Build executive visibility through metrics, decision materials, operating reviews, leadership updates, and recommendations
Lead and develop a small team of transformation program and workstream leads
Report to the Head of Technology Strategy, Transformation & Planning

Requirements

What you’ll need

Bachelor’s degree required; advanced degree or equivalent experience preferred
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 strong understanding of product management practices, technology delivery, and agile ways of working
Ability to shape work, define plans, prioritize activities, establish management routines, and drive measurable enterprise impact
Strong executive influence and stakeholder management skills
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 with AI-enabled transformation, engineering productivity, or digital/technology operating model change preferred
Experience building or leading transformation capabilities, including governance, execution discipline, adoption measurement, executive reporting, and value realization
Experience in management consulting, internal strategy, transformation office, enterprise program leadership, or technology operating model transformation strongly preferred
Must be legally authorized to work in the United States without employer sponsorship now or in the future

Benefits

Comp & perks

Annual, sales, or other incentive compensation may be available
Skill-building opportunities
Leadership development
Philanthropic opportunities
Contemporary, supportive, flexible, and inclusive benefits and resources
Benefits for full-time eligible employees
Equal opportunity and reasonable accommodation
Option to opt out of AI tools during the application process