Release Train Engineer

The Hartford•Chicago, IL

31d•Hybrid

About The Position

We're determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals - and to help others accomplish theirs, too. Join our team as we help shape the future. We are seeking a high-caliber, self-driven Release Train Engineer to lead the end-to-end execution, governance, and flow of the Middle & Large business Product Transformation value stream. This is not a traditional "ceremony facilitator" RTE role. You will operate as the COO of the value stream, owning delivery, predictability, risk posture, budgeting alignment, dependency management, and cross-functional orchestration across engineering, product, architecture, underwriting, and shared service teams. The ideal candidate is a systems leader who brings structure, clarity, and calm execution to complex programs, while championing an engineering-centric culture grounded in flow metrics, technical excellence, and accountability. You will be trusted to manage the value stream without requiring daily oversight from the VS leader - presenting information at the right altitude (CIO-ready high-level to deep operational detail) and demonstrating full control over scope, timelines, and risks. This role will have a Hybrid work schedule, with the expectation of working in an office (Columbus, OH, Chicago, IL, Hartford, CT or Charlotte, NC) 3 days a week (Tuesday through Thursday).

Requirements

7+ years of experience as RTE, Program Manager, or Senior Scrum Master in large-scale Agile environments
Proven ability to run complex ARTs/value streams across multiple products, teams, and domains
Deep experience with:
Flow metrics (flow time, load, efficiency, predictability)
WSJF prioritization
Risk and dependency management
PI Planning orchestration
Executive-level communication
Strong understanding of engineering processes (DevOps, CI/CD, testing, cloud, observability)
Exceptional facilitation, conflict resolution, and influence without authority
Ability to own delivery outcomes end-to-end with minimal oversight
Calm under pressure
Thinks in systems, not tasks
Obsessed with predictability and flow
Data-driven, not opinion-driven
Empathetic, but drives accountability
Able to challenge product, engineering, and architecture respectfully
High integrity; gives credit to engineering, never steals spotlight
Executive presence with humility and clarity
Candidate must be authorized to work in the US without company sponsorship.
The company will not support the STEM OPT I-983 Training Plan endorsement for this position.

Responsibilities

Own end-to-end delivery execution of epics and capabilities across multiple ARTs and teams.
Drive predictable delivery through flow metrics, capacity planning, dependency mapping, and risk management.
Ensure budget adherence, resource utilization visibility, and proactive forecasting.
Operate with a mindset of continuous improvement and operational excellence.
Translate VS strategy into executable roadmaps and PI objectives.
Run pre-PI activities to eliminate ambiguity before planning.
Coordinate sequencing, scope negotiation, and trade-offs with product, engineering, and architecture.
Ensure intake → estimation → prioritization → execution → release is smooth, scalable, and data-driven.
Build a proactive risk culture, not reactive fire-fighting.
Identify systemic blockers early using flow metrics, not opinions.
Maintain a transparent, no-surprises cadence with leadership.
Resolve multi-team conflicts with clarity, data, and executive presence.
Promote engineering fundamentals - design, quality, observability, testing, and technical debt visibility.
Ensure RTE function supports engineering, not substitutes for it.
Never operate as a "status collector"; own the details personally through systems, metrics, and direct engagement.
Give full credit to engineering leads and team members; reinforce high trust and high ownership culture.
Present status differently depending on audience:
CIO-level: outcomes, risks, decisions needed, high-level flow indicators.
Value Stream Leader: timeline, budget, cross-team risks, dependencies, bottlenecks, mitigation clarity.
Engineering/Team level: scope, impediments, alignment, actions, next steps.
Drive alignment without noise and create a predictable flow of communication.
Coach Scrum Masters, Program Teams, and Product partners on Lean-Agile practices and flow optimization.
Improve team health, team accountability, and cross-team collaboration.
Shift culture from "ceremony-driven" to data-driven, system-driven, and outcome-driven.