AVP, End User Engineering & Reliability

Assistant Vice President Of Engineering

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.

Key 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.

Required Knowledge

• AI-first engineering (central to this role):
  Proven leadership applying AI-first and AI-assisted engineering at scale - embedding generative AI, agentic automation, and AI-driven standards into how platforms are designed, built, and operated. This is the defining expectation of the role, and the successful candidate will set the standard for AI-first engineering across collaboration and workspace.
• Microsoft 365 ecosystem:
  Deep, current command of the collaboration and digital workspace estate (Teams, endpoint management, virtual desktop, etc.).
• Reliability / site reliability engineering: A track record in observability, and modern incident management.
• Outcome-based leadership:
  Fluency leading teams through OKR-based goal setting and outcome measurement.

Preferred (specific tooling):

• Intune;
  Windows 365 or Azure Virtual Desktop/Citrix; observability platforms (Nexthink, Dynatrace, Splunk);
  Terraform/Ansible;
  Power Shell/Python;
  Microsoft 365, including Power Platform, and Microsoft Copilot.

Required Qualifications

• 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).

Preferred Qualifications

• Familiarity with agentic operations / agentic Reliability Engineering and applying AI to operational…