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…