AVP, End User Engineering & Reliability

The Hartford•Hartford, CT

4d•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. The Hartford is accelerating toward AI-first engineering, and End User Services needs a leader to drive that shift across the platforms our employees rely on every day. We are seeking an Assistant Vice President of Engineering to lead the design, engineering, and reliability of our collaboration platforms (Teams, voice, conferencing, messaging) and digital workspace (endpoint, virtual desktop, identity-adjacent access, productivity tooling) and to operationalize Reliability Engineering across all of them. This is not a role to run these environments as they exist today. It is a mandate to re-engineer how they are built, operated, and measured: making AI-first engineering the default approach, operationalizing The Hartford's Reliability Engineering (RE) model, and managing the organization through OKRs so that availability, performance, and employee experience become measurable engineering outcomes rather than reactive, manually managed services.

Requirements

12+ years in technology engineering and operations, including 5+ years leading multi-team engineering organizations (managing managers/directors).
Proven record driving an AI-first or AI-assisted engineering transformation at scale - embedding AI and automation into how engineering teams build and operate.
A track record building or transforming a reliability engineering practice - SLOs, incident management, and measurable toil reduction.
Deep engineering background in collaboration and/or digital workspace platforms (Microsoft 365/Teams, voice, endpoint/EUC, virtual desktop, productivity tooling).
Hands-on credibility with automation and observability tooling.
Experience shifting an organization from operations-led to engineering-led delivery, including vendor and managed-service environments.
Experience leading through OKRs and outcome-based goal setting.
Enterprise-scale experience in a regulated industry (financial services/insurance preferred).
Based in or able to work in the greater Hartford, CT area on a hybrid schedule (three days per week in office).

Nice To Haves

Familiarity with agentic operations / agentic Reliability Engineering and applying AI to operational decision-making.
Experience standing up Digital Employee Experience (DEX) measurement and using it to drive investment.
Background in product-management practices applied to internal platforms.
Familiarity with chaos/resilience engineering and large-scale capacity planning.
Intune; Windows 365 or Azure Virtual Desktop/Citrix; observability platforms (Nexthink, Dynatrace, Splunk); Terraform/Ansible; PowerShell/Python; Microsoft 365, including Power Platform, and Microsoft Copilot.

Responsibilities

Set the engineering and reliability strategy for collaboration, digital workspace, and the platforms connecting them; translate it into a multi-year roadmap aligned to the CTO's AI-first engineering direction.
Set and own the engineering organization's OKRs - translating collaboration, workspace, reliability, and AI-first strategy into clear Objectives and measurable Key Results, aligned to CTO-level OKRs.
Operationalize Reliability Engineering across owned platforms – SLOs, incident standards, RE Squad integration, and run-operations-to-RE alignment - consistent with the firm's RE operating model.
Drive an AI-first, automation-first engineering culture - AI-first SDLC standards, infrastructure-as-code, automated and agentic remediation, release pipelines, and the systematic elimination of manual toil.
Build end-to-end observability and digital employee experience monitoring; make platform and experience health visible, predictive, and tied to business impact.
Lead, grow, and modernize a team of engineering directors and their organizations - raising the bar on technical depth, AI-first engineering practice, and reliability ownership.
Partner with security, identity, networking, infrastructure, and the Reliability Engineering community to deliver resilient, compliant, performant employee technology.
Own vendor and platform relationships from a position of engineering strength; ensure roadmaps, SLAs, and integrations meet our reliability and experience standards.
Define and report the Key Results that matter - availability and reliability (SLOs/SLIs, error budgets), AI-first adoption, digital employee experience, and toil/automation ratios - and review progress against OKRs with executive leadership on a regular cadence.