AVP, Digital Workplace Engineering

Role Overview

What's Different About This Role

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.
• 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; PowerShell/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 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.

Leadership Competencies

Work Arrangement

• Location: Hartford, CT (preferred), Charlotte, NC, or Columbus, OH.
• This position operates in a hybrid work environment. Candidates may be based in any of the listed locations.
• Relocation assistance is available for candidates who wish to relocate to Hartford, CT.
• Candidates must be authorized to work in the United States without employer sponsorship.

Compensation

• The annualized base pay range for this role is $201,500 - $302,500.
• The listed annualized base pay range is primarily based on analysis of similar positions in the external market.
• Actual base pay could vary and may be above or below the listed range based on factors including but not limited to performance, proficiency and demonstration of competencies required for the role.
• Other rewards may include short-term or annual bonuses, long-term incentives, and on-the-spot recognition.