AVP, Digital Workplace Engineering

The Hartford•Hartford, CT

2d•$201,500 - $302,500•Hybrid

About The Position

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 Digital Workplace 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. What's Different About This Role This position is intentionally scoped to bring capabilities that are underdeveloped in today's operating model. Success will be measured on closing these gaps: AI-first engineering — the defining expectation. Drive The Hartford's AI-first engineering agenda into the workspace and collaboration domains: embed AI-first standards, agentic and automated operations, and AI-assisted engineering into how the team builds and runs platforms. AI is the default engineering approach here, not a side initiative. This leader sets the bar for what AI-first looks like across the organization. From operations to Reliability Engineering. Operationalize the firm's RE model - SLOs/SLIs, error budgets, blameless postmortems, RE Squad integration, and alignment of run operations to RE strategy, rather than managing availability through escalation and heroics. From manual to automation-first. Drive self-healing, automated and agentic remediation, and AI discipline into environments that today depend on manual change and runbooks. From reactive to observable. Build telemetry, instrumentation, and proactive detection so issues are found and resolved before employees report them, replacing ticket volume as the primary signal of health. From service management to product engineering. Manage collaboration and workspace as products with roadmaps, adoption metrics, and a defined digital employee experience (DEX) practice, not a portfolio of vendor contracts to administer. From vendor-managed to engineering-led. Own the technical depth in-house and hold vendors to our engineering and reliability standards, rather than outsourcing architecture, integration, and accountability.

Requirements

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.
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

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.
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.

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.