Director, Technology Delivery and Release Management

Job Description

The Director, Technology Delivery & Release Management is a critical leadership role within the Workforce Benefits Technology organization. This position is responsible for ensuring delivery excellence, release governance, execution predictability, and operational readiness across the division's technology portfolio.

Success in this role requires a balanced combination of technology delivery leadership, release management expertise, operational governance, stakeholder management, and continuous improvement. This leader will champion delivery and release processes that foster quality, reliability, transparency, and alignment across interconnected product, platform, infrastructure, and vendor teams.

As the organization continues to scale, this leader will drive the evolution of delivery and release management capabilities while ensuring the technology ecosystem operates as a cohesive, predictable, and governable system. The role requires strong partnership across technology leadership, product management, business stakeholders, enterprise platform teams, and strategic vendors to deliver business value while minimizing execution and operational risk. The successful candidate will demonstrate exceptional organizational leadership, execution discipline, and the ability to influence outcomes across a highly matrixed environment.

This role requires being on-site 4 days per week in Newport Beach, CA, Charlotte, NC or Omaha, NE.

Core Accountabilities

• Accountable for delivery governance and execution excellence across the technology portfolio.
• Own release management strategy, governance, planning, coordination, and execution readiness.
• Drive transparency, accountability, and predictability across strategic initiatives and technology investments.
• Establish end-to-end delivery and release management standards, controls, and operating procedures.
• Coordinate dependencies across product teams, enterprise platforms, infrastructure teams, and vendors.
• Drive continuous improvement in delivery performance, release quality, and operational stability.
• Reduce delivery risk, release failures, production incidents, rework, and escalations through disciplined execution governance.

Key Responsibilities

Organizational Leadership

• Lead and develop a high-performing team of delivery managers and release managers.
• Establish a culture focused on accountability, execution excellence, operational discipline, and continuous improvement.
• Coach and mentor leaders across the portfolio to strengthen delivery capabilities and execution maturity.
• Partner with technology and business leadership to establish delivery priorities aligned to strategic objectives.
• Serve as a trusted advisor on delivery strategy, operational readiness, and release governance.

Technology Delivery Leadership

• Own delivery governance and execution assurance across product, platform, data, and integration teams.
• Establish delivery management processes that enable predictable outcomes while maintaining agility.
• Drive cross-functional planning and coordination for key strategic initiatives.
• Monitor milestone achievement, dependency management, and execution risks across the portfolio.
• Ensure initiatives are delivered on time, within scope, and aligned with agreed business outcomes.
• Facilitate executive delivery reviews and escalation management activities.

Release Management & Operational Readiness

• Own the division's release management operating model, governance framework, and release calendar.
• Lead release planning, readiness reviews, go-live governance, and post-release assessments.
• Ensure successful coordination of releases across multiple applications, platforms, and vendor partners.
• Establish release quality gates, deployment standards, rollback procedures, and risk management practices.
• Drive production readiness reviews and operational support preparedness prior to releases.
• Maintain executive visibility into release readiness, deployment risk, and operational impacts.
• Continuously improve deployment quality, efficiency, and predictability.

Strategic Planning & Portfolio Execution

• Partner with Product Management and Technology Leadership to establish and maintain delivery roadmaps.
• Align release schedules with business priorities, regulatory deadlines, and enterprise initiatives.
• Support annual planning, quarterly planning, and execution prioritization activities.
• Evaluate delivery capacity, execution constraints, and dependency risks across the portfolio.
• Drive successful execution of initiatives requiring coordination across enterprise technology organizations and vendor teams.

Vendor & Enterprise Partnership Leadership

• Partner closely with strategic vendors and enterprise platform teams to ensure delivery commitments are achieved.
• Lead governance activities related to external delivery organizations and release dependencies.
• Facilitate issue resolution and escalation management across vendors and enterprise stakeholders.
• Influence vendor delivery practices, release schedules, and resource allocation to support business objectives.
• Establish strong partnerships that improve delivery effectiveness and operational outcomes.

Metrics, Reporting & Transparency

• Define and maintain portfolio-level delivery, release, quality, and operational metrics.
• Develop executive-ready dashboards and reporting that provide visibility into delivery health and release performance.
• Provide actionable insights that enable data-driven decision-making and proactive risk mitigation.
• Establish governance forums that improve accountability and execution transparency.
• Track trends and identify systemic issues requiring organizational attention.

Enterprise & Matrix Leadership

• Partner with Product, Architecture, Infrastructure, Security, Finance, Procurement, Risk Management, and Enterprise Technology teams.
• Lead through influence across diverse stakeholder groups and organizational boundaries.
• Act as a stabilizing force during periods of organizational change, complex transformations, and critical delivery escalations.
• Drive alignment between business priorities and technology execution strategies.
• Foster collaboration across internal and external teams to achieve shared outcomes.

Qualifications

Required Experience

• Bachelor's degree in Computer Science, Information Systems, Engineering, Business, or a related field.
• 10+ years of experience leading technology delivery, program management, PMO, or release management functions.
• 5+ years of leadership experience managing managers, delivery organizations, or enterprise-scale programs.
• Proven success leading complex technology portfolios within a matrixed organizational structure.
• Deep experience establishing delivery governance and release management frameworks.
• Demonstrated success managing strategic initiatives involving multiple products, platforms, and external partners.
• Strong executive communication and stakeholder management skills.

Preferred Experience

• Experience within insurance, financial services, or other highly regulated industries.
• Experience supporting Agile Product Operating Models.
• Experience with enterprise SaaS platforms and third-party delivery organizations.
• Experience managing enterprise release trains and complex dependency management processes.
• PMP, SAFe, ITIL, Agile, or related leadership certifications.
• Demonstrated ability to apply AI-enabled tools and automation solutions to improve technology delivery, release management processes, performance reporting, and operational efficiency.

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Base Pay Range