Head of Transformation (AI)

Location: New York, NY, United States; hybrid with in-office attendance 3 days per week. Other location: Holmdel.

Salary: $178,690–$293,560 base pay annually; additional incentive compensation may apply.

Company

hirify.global is an insurance company focused on supporting professional and personal well-being through technology, leadership development, community-building, and inclusive benefits.

What you will do

• Own the integrated Digital and Technology transformation roadmap, including sequencing, milestones, dependencies, risks, executive decision points, and outcome accountability.
• Establish the transformation operating rhythm through workstream cadences, leadership forums, escalation paths, performance metrics, and blocker-removal mechanisms.
• Advance the product operating model with business and technology leaders, driving adoption and measurable maturity.
• Lead the AI Engineering and PDLC transformation program, translating pilot learnings into scaled practices, adoption metrics, and sustained behavior change.
• Connect strategy, portfolio, workforce, coaching, architecture, AI, and change-readiness priorities into a coherent transformation; partner on stakeholder planning, communications, readiness, and adoption measurement.
• Build executive visibility through metrics, decision materials, operating reviews, recommendations, and leadership updates; lead and develop a small team of transformation program and workstream leads.

Requirements

• Bachelor’s degree required; advanced degree or equivalent experience is 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 delivering successful programs across a matrixed enterprise.
• Experience in a product-led organization, with strong understanding of product management practices, technology delivery, and agile ways of working.
• Ability to turn ambiguity into clarity by shaping work, defining plans, prioritizing activities, establishing management routines, and driving measurable enterprise impact.
• Strong executive influence and stakeholder management skills, including advising senior leaders, framing enterprise-wide decisions, resolving cross-functional tension, and driving 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 covering governance, execution discipline, adoption measurement, executive reporting, and value realization.

Nice to have

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

Culture & Benefits

• Full-time role with contemporary, supportive, flexible, and inclusive benefits and resources.
• Support for professional and personal goals through skill-building and leadership development opportunities.
• Opportunities to participate in philanthropic initiatives and build communities with diverse colleagues.
• Benefits apply to eligible full-time employees.
• Guardian is an equal opportunity employer and provides reasonable accommodations during employment and the application process.