Benefits Enrollment & Billing Tech Transformation Lead

The Guardian Life Insurance Company of America; Holmdel Township (NJ); Hybrid; USD 155,000 - 255,000; Full time

Job summary

The Guardian Life Insurance Company of America seeks a Head of Group Benefits Enrollment and Billing Technology to lead the capabilities that onboard members, manage eligibility and enrollment, and enable accurate, timely billing across the Group Benefits value stream. You’ll guide multiple products and squads, aligning with business leaders to shape a modern technology vision.

Location: Holmdel, NJ with a hybrid schedule.

Qualifications

• 10+ years of technology or engineering experience, including leading strategy, architecture, and delivery for complex enterprise platforms.
• Proven track record modernizing legacy systems and delivering platform engineering, 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.
• Ability to shape long-term technology strategy, influence architectural direction, manage investment tradeoffs, and lead through ambiguity and organizational change.
• History of building high-performing, inclusive engineering cultures that attract, grow, and retain exceptional technical talent.
• Strong executive communication, with the ability to align senior leaders and teams around measurable outcomes.

Responsibilities

• Set and champion the domain-level technology strategy and architectural vision for Group Benefits enrollment and billing.
• Translate business strategies into multi-year modernization plans that simplify the enrollment-to-billing journey and retire legacy complexity.
• Own end-to-end technology outcomes across plan setup, eligibility, enrollment, member and coverage data, billing, adjustments, payments, and integrations.
• Oversee technical design and data governance, ensuring performance, resilience, security, auditability, and financial controls.
• Build and scale reusable engineering patterns, APIs, event-driven integrations, data quality controls, and automation that reduce manual work.
• Serve as trusted escalation point for complex technical decisions, production incidents, enrollment defects, billing discrepancies, and architectural risks.
• Develop, mentor, and elevate engineers, tech leads, quality engineers, and future leaders.
• Partner with Enrollment, Billing, Operations, Finance, Product, Distribution, Customer Service, Data & AI, and enterprise teams to drive cross-domain alignment.
• Collaborate with business product managers to define quarterly plans, outcomes, dependencies, controls, and commitments mapping to value stream OKRs.
• Influence funding decisions using measurable outcomes like enrollment quality, billing accuracy, efficiency, and reliability.
• Drive continuous improvement in automation, SDLC maturity, cloud adoption, observability, tooling, and production support.
• Enable teams to apply AI and automation to reduce exceptions, improve issue detection, and productivity.
• Establish and uphold world-class engineering standards across all products.

Skills

Leadership in tech strategy

Legacy modernization

Group benefits domain knowledge

Distributed systems

Cloud architectures

APIs & integration

Data quality & controls

Executive communication

Job description

The Guardian Life Insurance Company of America seeks a Head of Group Benefits Enrollment and Billing Technology to lead the capabilities that onboard members, manage eligibility and enrollment, and enable accurate, timely billing across the Group Benefits value stream. You’ll guide multiple products and squads, aligning with business leaders to shape a modern technology vision.

Location: Holmdel, NJ with a hybrid schedule.