Head of Group Benefits Enrollment and Billing Technology

Head of Group Benefits Enrollment and Billing Technology 

Position Overview 

As the Head of Group Benefits Enrollment and Billing Technology, you will serve as the strategic and technical leader for the capabilities that onboard members, manage eligibility and enrollment, and enable accurate, timely billing across the Group Benefits value stream. You will guide multiple products and squads while partnering closely with business product managers and owners to shape and execute a modern technology vision. Your leadership will simplify complex processes, modernize core platforms, strengthen data quality and controls, and drive secure, resilient delivery aligned to business value—fueling Guardian’s transformation and “Journey to 2030.” 

You will also be a force multiplier for our engineering community, cultivating the next generation of technology leaders across enrollment and billing. Through hands-on mentorship, coaching, and role-model leadership, you will inspire teams to deepen their domain expertise, strengthen engineering discipline, and embrace continuous improvement. You will champion automation, observability, quality engineering, and modern delivery practices that improve accuracy, throughput, and customer and partner experiences. 

Your leadership will transform strategy into measurable outcomes across the enrollment-to-billing lifecycle. You will translate ambitious business goals into clear, outcome-driven roadmaps; orchestrate complex initiatives spanning plan setup, eligibility, enrollment, member data, billing, payments, and integrations; and shape investment decisions with a strong focus on operational efficiency, financial accuracy, and risk reduction. You will partner across Value Stream, Platform, Data, AI, Finance, Operations, and Enterprise teams to drive alignment, scale, and sustained momentum. 

You Will (Responsibilities)

• Set and champion the domain-level technology strategy and architectural vision for Group Benefits enrollment and billing, ensuring products and platforms evolve cohesively toward a modern, scalable future. 

• Translate business strategies into multi-year modernization plans that simplify the enrollment-to-billing journey, retire legacy complexity, and improve speed, accuracy, and service outcomes. 

• Own end-to-end technology outcomes across plan setup, eligibility, enrollment, member and coverage data, billing, adjustments, payments, reconciliation, and related partner integrations. 

• Oversee technical design and data governance, ensuring performance, resilience, security, auditability, and financial controls remain uncompromising across squads and platforms. 

• Build and scale reusable engineering patterns, APIs, event-driven integrations, data quality controls, and automation that reduce manual work and improve straight-through processing. 

• Serve as the trusted escalation point for complex technical decisions, production incidents, enrollment defects, billing discrepancies, and architectural risks—providing clarity, direction, and decisive leadership. 

• Develop, mentor, and elevate engineers, tech leads, quality engineering professionals, and future leaders—strengthening both technical depth and enrollment and billing domain expertise. 

• Partner with Enrollment, Billing, Operations, Finance, Product, Distribution, Customer Service, Data & AI, and enterprise platform stakeholders to drive cross-domain alignment and unified outcomes. 

• Collaborate with business product managers and owners to define clear quarterly plans, outcomes, dependencies, controls, and commitments that map directly to value stream OKRs. 

• Influence funding prioritization and investment decisions using measurable business outcomes such as improved enrollment quality, billing accuracy, operational efficiency, platform reliability, and customer satisfaction. 

• Drive continuous improvement in automation, SDLC maturity, cloud adoption, observability, engineering tooling, release quality, and production support. 

• Enable teams to apply AI and intelligent automation to reduce enrollment exceptions, improve billing issue detection, accelerate resolution, and enhance employee productivity. 

• Establish and uphold world-class engineering standards—CI/CD, testing, security, supportability, data quality, controls, and metrics—ensuring consistent excellence across all products. 

You Have  (Required Skills)

• 10+ years of technology or engineering experience, including demonstrated success leading strategy, architecture, and delivery for complex enterprise platforms. 

• A proven track record modernizing legacy systems and delivering platform engineering, process automation, and operational improvements at enterprise scale. 

• Strong knowledge of group benefits, employee benefits, insurance, or adjacent financial-services domains; direct experience with eligibility, enrollment, billing, payments, or reconciliation is strongly preferred. 

• Deep technical expertise across distributed systems, cloud architectures, APIs, integration patterns, data platforms, event-driven design, security, and modern engineering practices. 

• Demonstrated ability to improve data quality, financial accuracy, operational controls, resilience, and customer outcomes across complex business processes. 

• The ability to shape long-term technology strategy, influence architectural direction, manage investment tradeoffs, and lead through ambiguity and organizational change. 

• A history of building high-performing, inclusive engineering cultures that attract, grow, and retain exceptional technical talent. 

• Strong executive-level communication, with the ability to align senior leaders, business and technology partners, and cross-functional teams around measurable outcomes. 

Location:

• Hybrid Work arrangement with three days a week at a Guardian office in Holmdel, NJ, Bethlehem, PA or New York, NY.

Salary Range:

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 [email protected]. 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.

Notice Regarding Guardian’s Use of Artificial Intelligence in Recruitment

As part of Guardian’s job application process, Guardian may use artificial intelligence tools (“AI Tools") to automate the sorting and filtering of information provided by applicants as part of its preliminary screening. This preliminary screening may be used to help identify applicant materials and resumes relative to their indication that the applicant meets the requirements for the specific job for which they are applying, as specified in the listing posted on Guardian’s jobs website (Careers at Guardian at https://www.guardianlife.com/careers). At Guardian, we do not use AI Tools to substantially assist or replace human judgment or discretionary decision making in our hiring process. All hiring decisions will be made by Guardian colleagues.

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 [email protected], 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 [email protected].

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.