Sr. Release Train Engineer

Independence Pet Group•Chicago, IL

About The Position

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: IPH is executing a multi-year transformation to modernize its insurance technology ecosystem across multiple MGAs, including policy administration, rating, billing, claims, integrations, digital experience, data, and cybersecurity. The Senior Release Train Engineer (Senior RTE) is the primary execution leader across one or more Agile Release Trains (ARTs) supporting this global transformation. This role is responsible for ensuring program-level flow, dependency management, and predictable delivery across distributed teams, multiple System Integrators, and cross-functional technology and business partners. The Senior RTE works side-by-side with the Sr. Technology Program Manager, Global Transformation and plays a critical role in enabling Scaled Agile (SAFe) delivery, orchestrating vendor teams, aligning stakeholders, and driving continuous improvement across the transformation. This is a senior, highly visible role requiring deep SAFe expertise, insurance delivery experience, and the ability to coordinate complex delivery environments across North America, Europe, and offshore partners.

Requirements

8+ years of technology delivery experience, including 5+ years as an RTE in a Scaled Agile (SAFe) environment.
Hands-on experience supporting large, complex transformation programs, ideally within insurance or financial services.
Strong understanding of insurance value streams: policy admin, billing, claims, rating, underwriting, servicing, and MGA operations.
Proven ability to coordinate multiple system integrators (SIs) and large vendor ecosystems across distributed global teams.
Deep expertise facilitating SAFe ceremonies, PI Planning, ART Syncs, Scrum of Scrums, and dependency mapping.
Ability to lead teams in highly matrixed environments and influence without direct authority.
Strong understanding of APIs, integrations, data flows, and modern enterprise architecture concepts.
Excellent communication, facilitation, negotiation, and stakeholder management skills.

Nice To Haves

Experience with EIS, Guidewire, Duck Creek, Socotra, Majesco, or similar core insurance platforms.
SAFe RTE, SPC, or SASM certification.
Experience working in multi-MGA environments.
Familiarity with Smartsheet, Jira Align, ADO, or other scaled work-management tools.
Experience working with offshore, nearshore, and European teams.
Experience supporting a Technology PMO or Transformation Office.

Responsibilities

ART Leadership & SAFe Execution Serve as the Senior RTE across one or more large-scale ARTs supporting the enterprise transformation.
Lead all SAFe ceremonies: PI Planning, Scrum of Scrums, ART Sync, System Demo, I&A, and release-readiness reviews.
Establish, mature, and continuously improve agile release train practices and delivery discipline.
Program Increment (PI) Planning & Delivery Cadence Own end-to-end PI Planning execution — pre-planning, facilitation, alignment, and post-PI tracking.
Maintain the program board, ensuring clear visualization of dependencies, risks, objectives, and sequencing.
Ensure teams are aligned on PI Objectives, commitments, and delivery impacts.
Execution Management & Flow Optimization Drive flow across teams and workstreams by identifying and removing blockers, escalating impediments, and accelerating decisions.
Coordinate engineering, architecture, QA, data, infrastructure, security, and external vendor teams.
Ensure stable delivery across integrations, data pipelines, platform upgrades, and shared services.
Vendor & System Integrator (SI) Coordination Partner with multiple global SIs (e.g., Capgemini, Hexaware, Microsoft, Cognizant/TCS if involved).
Ensure vendor teams follow SAFe delivery practices, maintain quality, and honor milestones.
Track vendor performance against SOW commitments and provide insights to the Sr. Program Manager.
Cross-Team Dependency & Risk Management Identify dependencies across applications, integrations, policy admin, billing, claims, data, and security domains.
Drive alignment across internal and vendor teams to mitigate delivery risks.
Manage cross-ART and cross-team commitments, sequencing, and release alignment.
Global Coordination Work with JAB Pet Services teams in the UK and Europe to align PI plans, architectural standards, release patterns, and shared capabilities.
Manage time-zone coordination across US, offshore, and European teams.
Governance & Reporting Maintain transparency through real-time dashboards, flow metrics, predictability measures, and risk registers.
Contribute to TPMO governance rituals and provide concise, executive-ready delivery updates.
Track ART health, team performance, velocity trends, and quality indicators.
Continuous Improvement & Coaching Coach Scrum Masters, Product Owners, engineering leads, and vendor teams on SAFe best practices.
Facilitate Inspect & Adapt to strengthen problem-solving and quality outcomes.
Foster an environment of continuous learning, transparency, and delivery excellence.