Head of Purchase and Underwriting Transformation (Pittsfield)

We are seeking a strategic, ambitious, and entrepreneurial leader to serve as Head of Purchase & Underwriting Transformation, a highly visible leadership role responsible for shaping and delivering the future of Guardian’s purchase experience and underwriting capabilities across Life, Disability, and Annuity products. This program plays a foundational role in Guardian Financial Protection and Retirement Solutions’ (FPRS) Journey-to-30 strategy. Our objective is clear—make purchasing protection and retirement solutions frictionless by minimizing evidence requirements using third party data and develop machine learning models to make pricing more dynamic and granular. Offer turnaround times should take minutes rather than weeks or months with little to no effort required by an applicant and no rework when applying for multiple coverages. In this role, you will lead the strategic modernization of the purchase and underwriting ecosystem, helping define the long‑range vision for how customers, advisors, and colleagues experience the application, risk management, and policy activation journeys. You will partner with senior leaders to translate this bold vision into a multiyear roadmap with prioritized work efforts aligned with measurable outcomes, powered by modern platforms, advanced data, automation, and AI‑enabled decisioning. In addition to managing a team of transformation consultants, product managers, and product owners aligned to the various systems, you will work across business units and corporate functions to deliver material improvements in advisor productivity, prospect conversion, operational efficiency, and risk outcomes. This will include collaborating with colleagues across Product, Pricing, and Underwriting, Distribution, Data & Technology, and Data Science, amongst other important functional stakeholders.A successful candidate will set bold strategic direction, delivering a clear and compelling business case, and aligning investments and resources. You and your team must ensure initiatives are delivered efficiently and effectively, while also managing a comprehensive go-to-market plan that drives in market adoption of new capabilities.What You Will DoYour work will span across the following areas:Enterprise Strategy, Innovation & Value DeliveryDefine and execute a multi‑year transformation vision, strategy, and roadmap for Purchase and Underwriting, aligned to enterprise priorities, manufacturing objectives, and growth goals.Identify, evaluate, and prioritize high‑impact initiatives that improve customer and advisor experience, underwriting effectiveness, and operational scalability.Establish and monitor clear success measures, KPIs, and financial outcomes to ensure transparency and accountability for value realization.Purchase Experience TransformationLead modernization of the end‑to‑end purchase experience, including eApp, eMed, eDelivery, orchestration, and omni‑channel journeys.Drive digitization and automation to reduce customer and advisor effort, increase transparency, and accelerate placement and cycle times.Partner with Distribution, Marketing, Operations, and Technology to ensure purchase capabilities are seamlessly executed and broadly adopted.Own Guardian’s Underwriting Transformation and Innovation agenda, including automation, data‑driven underwriting, and AI‑enabled decisioning.Champion the adoption of advanced technologies such as GenAI, predictive analytics, triage models, and auto‑assessment tools across underwriting workflows.Improve underwriting productivity, flow case handling, placement rates, scalability, and risk outcomes while maintaining strong governance and regulatory compliance.Guide the integration of new data sources, decision engines, and modern architectures into core underwriting processes.Operating Model & Execution LeadershipProvide clear leadership across cross‑functional teams delivering purchase and underwriting initiatives, reinforcing disciplined execution and outcome‑based delivery.Partner closely with Technology, Data, and Platform leaders to manage dependencies, sequencing, and delivery at enterprise scale.Apply BTOM principles and ways of working pragmatically to drive clarity, accountability, and sustained performance.Investment, Governance & Stakeholder LeadershipOwn investment strategy and funding trade‑offs across Purchase and Underwriting Transformation, ensuring spend is tied to measurable outcomes.Lead and participate in governance forums, including underwriting and purchase transformation steer‑cos and cross‑functional workstreams.Serve as an executive sponsor for change management, communications, and adoption across impacted teams.Act as a primary liaison with key internal stakeholders, vendors, and external partners as needed.Talent & Capability DevelopmentBuild, lead, and develop high‑performing, multidisciplinary teams spanning underwriting, analytics, technology, and subject‑matter expertise.Foster a culture of innovation, collaboration, continuous learning, and knowledge sharing.Partner with HR and enterprise centers of excellence to strengthen leadership capability and succession.You AreA strategic problem‑solver, with demonstrated experience using structured frameworks and analysis to make data‑driven decisions and recommendations for complex problems without easy answers.Experienced in executing strategy and transformation initiatives, including scoping work, managing timelines, and conducting or overseeing quantitative and qualitative analyses to deliver actionable, impactful recommendations.An effective influencer with strong interpersonal skills, maturity, and judgment, able to align senior stakeholders and cross‑functional teams.A confident communicator, both written and verbal, with experience presenting to senior audiences in highly visible forums.Highly organized and efficient, with the ability to prioritize across multiple initiatives and competing demands, while using time and forums thoughtfully and effectively.Results‑oriented and pragmatic, focused on driving real, tangible impact and ensuring strategies can be operationalized and sustained.Intellectually curious and innovation‑minded, consistently asking “what’s next?” and exploring new approaches to improve outcomes.You Have10+ years of experience in life insurance or financial services, including leadership roles within underwriting, manufacturing, operations, or transformation.Proven success leading large‑scale transformation initiatives with measurable business outcomes.Demonstrated experience implementing AI‑enabled, data‑driven, and automated underwriting or insurance solutions.Deep understanding of life insurance underwriting, distribution models, competitive dynamics, and regulatory requirements.Strong financial, portfolio, and business judgment.Experience working effectively in highly matrixed, enterprise environments.Bachelor’s degree required; advanced degree preferred.You WillShape the future of Guardian’s purchase and underwriting capabilities through innovation, digitization, and modern decisioning.Influence and partner closely with Guardian senior executives and functional leaders.Lead some of the company’s most visible and strategically important transformation initiatives.Build deep expertise across businesses, functions, and advanced technologies.Salary Range:$155,370.00 - $255,255.00The 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 PromiseAt 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-BeingAs 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 . Benefits apply to full-time eligible employees. Interns are not eligible for most Company benefits.Equal Employment OpportunityGuardian 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.AccommodationsGuardian 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 View email address on apply.placed-app.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 SponsorshipGuardian is not currently or in the foreseeable future sponsoring employment visas. In order to be a successful applicant. you must be legally authorized to work in the United States, without the need for employer sponsorship.Notice Regarding Guardian’s Use of Artificial Intelligence in RecruitmentAs part of Guardian’s job application proces