Technology Program Director - Enterprise Transformation

Independence Pet Group•Chicago, IL

About The Position

Independence Pet Holdings (IPH) is seeking a Technology Program Director for Enterprise Transformation. This role is crucial for a multi-year initiative to modernize the company's insurance technology ecosystem and build a scalable, digital-first operating model. The Common Core organization within IPH is responsible for building and operating shared platforms and services that will power the future-state operating model, encompassing areas like Insurance, Customer Journey, Agentic AI, Data, Integrations, Digital Experiences, and other shared enterprise services. The Technology Program Director will lead the execution and coordinated delivery across the Common Core portfolio, reporting to the Technology Portfolio & Delivery Office (TPDO). This role acts as the primary delivery partner to Common Core leadership, overseeing governance, integrated planning, dependency management, mobilization, release readiness, operational readiness, and execution coordination across multiple transformation workstreams. The position also provides leadership to Program Managers and delivery enablement functions, ensuring successful transformation outcomes for one of IPH's most strategic initiatives.

Requirements

12+ years of technology program, portfolio, or transformation management experience supporting large-scale enterprise initiatives.
Experience leading Program Managers, PMO functions, release management teams, service management functions, delivery organizations, or transformation offices.
Experience leading cross-functional programs involving business, technology, operations, vendors, and external delivery partners.
Experience managing system integrators, offshore delivery teams, and third-party vendors.
Experience supporting enterprise platform implementations, digital transformation programs, cloud modernization, customer experience initiatives, AI enablement, or large-scale operating model transformations.
Experience working within Agile / SAFe delivery environments.
Strong understanding of enterprise delivery governance, reporting, financial tracking, dependency management, release management, operational readiness, and portfolio management practices.
Strong transformation leadership and execution management skills across complex enterprise technology and business initiatives.
Demonstrated experience leading Program Managers, PMO functions, release management teams, service management functions, or delivery organizations.
Ability to manage competing priorities and operate effectively within fast-paced transformation environments.
Strong organizational, planning, dependency management, facilitation, and problem-solving capabilities.
Excellent communication and stakeholder management skills with the ability to coordinate across business, technology, and vendor organizations.
Experience leading Agile / SAFe delivery models and large-scale cross-functional delivery coordination.
Ability to facilitate collaboration across distributed teams, vendors, system integrators, and executive stakeholders.
Strong attention to detail combined with the ability to maintain visibility across interconnected workstreams and dependencies.
Demonstrated ability to proactively identify risks, escalate issues, drive execution transparency, and ensure accountability across delivery teams.
Acts as a collaborative leader who promotes accountability, continuous improvement, operational excellence, and execution discipline.

Nice To Haves

Experience supporting transformation initiatives within insurance, financial services, healthcare, or other regulated industries.

Responsibilities

Lead execution and coordinated delivery across strategic transformation initiatives supporting Common Core business and technology capabilities.
Provide leadership and direction to Program Managers and delivery enablement functions supporting governance, release readiness, operational readiness, and execution coordination activities.
Serve as the primary delivery partner to Common Core leadership, ensuring alignment between strategic objectives, roadmap commitments, and execution outcomes.
Drive integrated planning and execution coordination with business leaders, product leaders, architects, engineers, program managers, and system integrators.
Lead Agile / SAFe delivery routines, including Program Increment (PI) Planning, dependency management, governance reviews, RAID management, and execution tracking activities.
Lead integrated roadmap coordination across Insurance, Customer Journey, Agentic AI, Data, Infrastructure, Security, Digital, and shared platform workstreams.
Drive visibility and accountability for program milestones, dependencies, risks, issues, financials, and action items across multiple delivery teams.
Lead coordination with vendors and third-party delivery partners to monitor deliverables, escalate blockers, and ensure execution accountability.
Build and maintain executive-ready dashboards, governance materials, status reporting, and operational metrics supporting transformation leadership.
Partner with Enterprise Architecture, Infrastructure, Information Security, Data, Product, and Engineering teams to ensure aligned and predictable delivery outcomes.
Lead the establishment of release governance, operational readiness, service management processes, and transition-to-support frameworks supporting Common Core capabilities and the broader Pawprint transformation.
Ensure delivery activities align with TPDO governance standards, reporting requirements, financial controls, and operational processes.
Collaborate closely with Common Core leadership and business stakeholders to ensure alignment between delivery activities and broader transformation objectives.
Establish delivery accountability across Program Managers and delivery teams while promoting operational excellence, continuous improvement, and execution discipline.
Contribute to the development and maturation of portfolio management, delivery governance, planning standards, reporting practices, service management processes, and transformation execution disciplines across IPH.