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Chicago, Illinois, United States
Hybrid
Established in 2021, Independence Pet Holdings is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.
We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.
Job Summary:
Independence Pet Holdings (IPH) is undertaking a multi-year enterprise transformation to modernize its insurance technology ecosystem and build a scalable, digital-first operating model across its MGAs.
A key component of Pawprint is Common Core, a technology organization responsible for building and operating the shared platforms, services, and capabilities that will power the future-state operating model. Common Core includes capabilities spanning Insurance, Customer Journey, Agentic AI, Data, Integrations, Digital Experiences, and other shared enterprise services that collectively form the Skylark platform ecosystem.
The Technology Program Director – Enterprise Transformation is responsible for leading execution and coordinated delivery across the Common Core portfolio. Reporting into the Technology Portfolio & Delivery Office (TPDO), this role serves as the primary delivery partner to Common Core leadership and is accountable for governance, integrated planning, dependency management, mobilization, release readiness, operational readiness, and execution coordination across multiple transformation workstreams.
The role provides leadership to Program Managers and delivery enablement functions responsible for release governance, service management process ownership, operational readiness, and execution coordination supporting Common Core capabilities. Working closely with business leaders, product leaders, architects, engineers, vendors, and system integrators, the successful candidate will drive delivery accountability, organizational readiness, and successful transformation outcomes across one of IPH's most strategic initiatives.
Focus Areas
Transformation Delivery Leaders: Lead execution and coordinated delivery across strategic transformation initiatives supporting Common Core business and technology capabilities.
Delivery Governance & Operational Readiness: Establish governance, release management, service management, and operational readiness capabilities required to successfully transition Common Core platforms and services from implementation into sustainable operations
Program Governance: Establish and maintain governance structures, executive reporting, decision forums, and operational cadences that support successful transformation outcomes
Integrated Planning & Dependency Management: Drive coordination across business, technology, architecture, engineering, vendor, and partner teams to manage priorities, dependencies, milestones, risks, assumptions, and execution readiness.
Agile Delivery Enablement: Support Agile and SAFe delivery practices, including Program Increment (PI) planning, dependency management, release readiness, and cross-functional execution coordination.
Vendor & Partner Coordination: Partner with system integrators, consulting organizations, and technology providers to ensure delivery commitments, quality standards, and transformation objectives are achieved
Key Responsibilities:
Lead and coordinate delivery activities across strategic enterprise 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.
Required Skills & Abilities:
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.
Education and Experience:
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.
Experience supporting transformation initiatives within insurance, financial services, healthcare, or other regulated industries preferred
#IPH
All of our jobs come with great benefits including healthcare, parental leave and opportunities for career advancements. Some offerings are dependent upon the location of where you work and can include the following:
Comprehensive full medical, dental and vision Insurance
Basic Life Insurance at no cost to the employee
Company paid short-term and long-term disability
12 weeks of 100% paid Parental Leave
Health Savings Account (HSA)
Flexible Spending Accounts (FSA)
Retirement savings plan
Personal Paid Time Off
Paid holidays and company-wide Wellness Day off
Paid time off to volunteer at nonprofit organizations
Pet friendly office environment
Commuter Benefits
Group Pet Insurance
On the job training and skills development
Employee Assistance Program (EAP)
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