Head of Transformation

Guardian’s Digital and Technology (D&T) organization is undergoing a transformation—scaling the product operating model, embedding AI-enabled ways of working, and strengthening execution discipline across the organization. As Head of Transformation, you will own the integrated roadmap, workstream sequencing, dependency management, executive visibility, and outcome accountability required to turn D&T’s strategy into measurable progress. This role is expected to operate as an enterprise transformation leader—shaping priorities with senior executives, driving tradeoff decisions, holding workstream owners accountable, and building the transformation capability required to sustain change at scale. This is an opportunity to help shape the next phase of Guardian’s D&T transformation, working directly with senior leaders on high-priority initiatives and driving successful outcomes. You are A transformation leader who can translate strategy into execution, bring clarity to ambiguity, create structure across complex work, and influence senior leaders to make decisions, align on tradeoffs, and remove barriers. You are energized by large-scale change, comfortable working across product, engineering, AI and operating model topics, and able to translate strategy into practical execution plans that teams can act on. You are equally strong at setting direction, creating management systems, and leading through others to ensure transformation commitments translate into sustained operating changes. The ideal candidate will have a unique blend of consulting skills, strategic thinking, creativity, and executional excellence and is passionate about creating impactful change for the organization. You have Bachelor’s degree required;margin-top:6.0pt;">Bachelor’s degree required;margin-top:6.0pt;">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. ;margin-top:6.0pt;">10-15 years of experience leading enterprise transformation, technology strategy, operating model, product model, or complex cross-functional change programs.;margin-top:6.0pt;">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. ;margin-top:6.0pt;">Experience leading strategic initiatives, developing roadmaps, and driving successful programs across a matrixed enterprise.;margin-top:6.0pt;">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. ;margin-top:6.0pt;">Experience working in a product-led organization, with strong understanding of product management practices, technology delivery, and agile ways of working.;margin-top:6.0pt;">Experience working in a product-led organization, with 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. ;margin-top:6.0pt;">Demonstrated ability to move from ambiguity to clarity by shaping work, defining plans, prioritizing activities, establishing management routines, and driving measurable enterprise impact.;margin-top:6.0pt;">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. ;margin-top:6.0pt;">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.;margin-top:6.0pt;">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. ;margin-top:6.0pt;">Ability to synthesize complex work into clear narratives, decision materials, operating reviews, and leadership updates.;margin-top:6.0pt;">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. ;margin-top:6.0pt;">Experience with AI-enabled transformation, engineering productivity, or digital/technology operating model change preferred.;margin-top:6.0pt;">Experience with AI-enabled transformation, engineering productivity, or digital/technology operating model change preferred. Experience building or leading transformation capabilities, including standards for governance, execution discipline, adoption measurement, executive reporting, and value realization. ;margin-top:6.0pt;">Experience building or leading transformation capabilities, including standards for governance, execution discipline, adoption measurement, executive reporting, and value realization.;margin-top:6.0pt;">Experience building or leading transformation capabilities, including standards for 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. ;margin-top:6.0pt;">Experience in management consulting, internal strategy, transformation office, enterprise program leadership, or technology operating model transformation strongly preferred.;margin-top:6.0pt;">Experience in management consulting, internal strategy, transformation office, enterprise program leadership, or technology operating model transformation strongly preferred. You will Own the integrated transformation roadmap across D&margin-top:6.0pt;">Own the integrated transformation roadmap across D&margin-top:6.0pt;">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. ;margin-top:6.0pt;">Establish and manage the transformation operating rhythm, including workstream cadences, leadership forums, escalation paths, performance metrics, and mechanisms to remove blockers quickly.;margin-top:6.0pt;">Establish and manage the transformation operating rhythm, including workstream cadences, leadership forums, escalation paths, performance metrics, and mechanisms to remove blockers quickly. Lead the continued advancement of the product operating model, partnering with coaching center of excellence, and business and technology leaders to drive adoption and measurable maturity. ;margin-top:6.0pt;">Lead the continued advancement of the product operating model, partnering with coaching center of excellence, and business and technology leaders to drive adoption and measurable maturity.;margin-top:6.0pt;">Lead the continued advancement of the product operating model, partnering with coaching center of excellence, and business and technology leaders to drive adoption and measurable maturity. Drive the AI Engineering and PDLC transformation program in partnership with Engineering Enablement, ensuring pilot learnings translate into scaled practices, adoption metrics, and sustained behavior change. ;margin-top:6.0pt;">Drive the AI Engineering and PDLC transformation program in partnership with Engineering Enablement, ensuring pilot learnings translate into scaled practices, adoption metrics, and sustained behavior change.;margin-top:6.0pt;">Drive the AI Engineering and PDLC transformation program in partnership with Engineering Enablement, ensuring pilot learnings translate into scaled practices, adoption metrics, and sustained behavior change. Ensure transformation priorities are connected across strategy, portfolio, workforce, coaching, architecture, AI, and change readiness so workstreams add up to one coherent transformation. ;margin-top:6.0pt;">Ensure transformation priorities are connected across strategy, portfolio, workforce, coaching, architecture, AI, and change readiness so workstreams add up to one coherent transformation.;margin-top:6.0pt;">Ensure transformation priorities are connected across strategy, portfolio, workforce, coaching, architecture, AI, and change readiness so workstreams add up to one coherent transformation. Partner with Strategy and Change leaders to ensure each transformation workstream has a clear stakeholder plan, readiness approach, communications path, and adoption measurement. ;margin-top:6.0pt;">Partner with Strategy and Change leaders to ensure each transformation workstream has a clear stakeholder plan, readiness approach, communications path, and adoption measurement.;margin-top:6.0pt;">Partner with Strategy and Change leaders to ensure each transformation workstream has a clear stakeholder plan, readiness approach, communications path, and adoption measurement. Build executive visibility into transformation progress through clear metrics, decision materials, operating reviews, fact-based leadership updates, and clear recommendations that enable timely senior-level decisions. ;margin-top:6.0pt;">Build executive visibility into transformation progress through clear metrics, decision materials, operating reviews, fact-based leadership updates, and clear recommendations that enable timely senior-level decisions.;margin-top:6.0pt;">Build executive visibility into transformation progress through clear metrics, decision materials, operating reviews, fact-based leadership updates, and clear recommendations that enable timely senior-level decisions. Lead and develop a small team of transformation program and workstream leads who structure the work, build plans, manage blockers, drive outcomes, and raise the overall transformation capability across D&margin-top:6.0pt;">Lead and develop a small team of transformation program and workstream leads who structure the work, build plans, manage blockers, drive outcomes, and raise the overall transformation capability across D&margin-top:6.0pt;">Lead and develop a small team of transformation program and workstream leads who structure the work, build plans, manage blockers, drive outcomes, and raise the overall transformation capability across D&T. Reporting Relationships This role will report to the Head of Technology Strategy, Transformation & Planning and will lead transformation program and workstream leads. Location The primary location for this position is New York, NY. Salary Range: $178,690.00 - $293,560.00 The salary range reflected above is a good faith estimate of base pay for the primary location of the position. The salary for this position ultimately will be determined based on the education, experience, knowledge, and abilities of the successful candidate. In addition to salary, this role may also be eligible for annual, sales, or other incentive compensation. Our Promise At Guardian, you’ll have the support and flexibility to achieve your professional and personal goals. Through skill-building, leadership development and philanthropic opportunities, we provide opportunities to build communities and grow your career, surrounded by diverse colleagues with high ethical standards. Inspire Well-Being As part of Guardian’s Purpose – to inspire well-being – we are committed to offering contemporary, supportive, flexible, and inclusive benefits and resources to our colleagues. Explore our company benefits at www.guardianlife.com/careers/corporate/benefits. Benefits apply to full-time eligible employees. Interns are not eligible for most Company benefits. Equal Employment Opportunity Guardian is an equal opportunity employer. All qualified applicants will be considered for employment without regard to age, race, color, creed, religion, sex, affectional or sexual orientation, national origin, ancestry, marital status, disability, military or veteran status, or any other classification protected by applicable law. Accommodations Guardian is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. Guardian also provides reasonable accommodations to qualified job applicants (and employees) to accommodate the individual's known limitations related to pregnancy, childbirth, or related medical conditions, unless doing so would create an undue hardship. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact MyHR@glic.com. Please note: this resource is for accommodation requests only. For all other inquires related to your application and careers at Guardian, refer to the Guardian Careers site. Visa Sponsorship Guardian Life is not currently or in the foreseeable future sponsoring employment-based visas (e.g., such as an H-1B). In order to be a successful applicant, you must be legally authorized to work in the United States, without the need for employer sponsorship/support now or at any time in the future. 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Please be aware that if you apply for a specific position with Guardian, you will have the choice of opting out of Guardian’s use of AI Tools during the job application process. If you would like to request an alternative process that does not utilize AI Tools or would like to request a reasonable accommodation, within ten business days of your position application, you must email your request to MyHR@glic.com, making sure to provide your name and job requisition identification number. Guardian will retain your applicant materials and resume and all information therefrom in accordance with Guardian’s document retention policy, a copy of which you may request via MyHR@glic.com. Additionally, at applicable times, Guardian will make public the most recent bias audit results for such AI tools, which may be found here. Current Guardian Colleagues: Please apply through the internal Jobs Hub in Workday. Every day, Guardian helps our 29 million customers realize their dreams through a range of insurance and financial products and services. Our Purpose, to inspire well-being, guides our dedication to the colleagues, consumers, and communities we serve. We know that people count, and we go above and beyond to prepare them for the life they want to live, focusing on their overall well-being — mind, body, and wallet. As one of the largest mutual insurance companies, we put our customers first. Behind every bright future is a GuardianTM. Learn more about Guardian at guardianlife.com. Visa Sponsorship: Guardian Life is not currently or in the foreseeable future sponsoring employment-based visas (e.g., such as an H-1B). In order to be a successful applicant, you must be legally authorized to work in the United States, without the need for employer sponsorship/support now or at any time in the future.