Group Engineering Manager - Calendar Scheduling

Microsoft•Redmond, WA

About The Position

We are looking for a Group Engineering Manager (GEM) to lead the Calendar Scheduling engineering org—a mission-critical pillar of Microsoft’s Calendar and Copilot experiences. This role will lead the teams that build the end-to-end scheduling stack: helping people find the right time faster, navigate constraints, reduce back and forth, and confidently get meetings scheduled. Scheduling is one of the hardest problems in productivity: it combines human preferences, organizational norms, time zones, recurrence, resource constraints, and rapidly changing context. Our ambition is to turn scheduling into a high-trust agentic workflow—moving users up the ladder from assist → propose → delegate → agency. You’ll lead the transformation from “Copilot helps me schedule” to “a calendar that runs itself”—where Copilot can proactively manage conflicts, negotiate time on a user’s behalf, and execute scheduling work end-to-end across clients, services, and partner surfaces, while meeting Microsoft-scale expectations for reliability and trust. Ship at Microsoft Scale Drive execution across multiple scheduling workstreams with dependencies on shared platform teams and partner experiences. Make principled tradeoffs between capability, velocity, privacy/security, and operational reliability. Operate effectively in a fast-paced, large, cross-org environment—building alignment while keeping delivery crisp. Raise the bar on engineering excellence: telemetry, experimentation rigor, evaluation frameworks, and live-site health. What Success Looks Like Agentic Scheduling becomes the default path for users because it consistently saves time and reduces friction. Scheduling in Microsoft Calendar is considered gold standard when compared to other scheduling systems. The experience is trusted: users don’t second-guess calendar copilot, and outcomes feel explainable and dependable. Engineering teams thrive: strong ownership, product judgment, high craft, and a culture of inclusion and accountability. Teams can execute rapidly, experimenting on a daily basis making data driven decisions. Microsoft’s mission is to empower every person and every organization on the planet to achieve more. As employees we come together with a growth mindset, innovate to empower others, and collaborate to realize our shared goals. Each day we build on our values of respect, integrity, and accountability to create a culture of inclusion where everyone can thrive at work and beyond.

Requirements

Bachelor's Degree in Computer Science or related technical field AND 8+ years technical engineering experience with coding in languages including, but not limited to, C, C++, C#, Java, or Python
OR equivalent experience.

Nice To Haves

Solid technical background in distributed systems (service design, scale, reliability, and operations).
Experience building AI-powered experiences or agentic workflows where trust and quality are central.
Hands on experience with evaluation frameworks, experimentation, and telemetry for AI systems (quality, safety, regressions, satisfaction).
Proven experience leading multiple teams and/or managers in complex, cross-cutting product areas.
10+ years of professional engineering experience, including 3+ years of managing multiple engineering teams.
Track record of shipping customer-facing features with high quality, adoption, and operational maturity.
Excellent written and verbal communication—able to align stakeholders and articulate crisp tradeoffs.
Solid product judgment—knowing when “good enough” is not good enough, and where simplicity beats cleverness.

Responsibilities

Own the technical vision, strategy, and multi-year roadmap for Calendar Scheduling—partnering closely with product and senior leadership.
Lead multiple teams across core scheduling capabilities, platform components, and end-to-end user outcomes.
Drive architecture and design quality, ensuring solutions are scalable, maintainable, and aligned with long-term strategy.
Deliver measurable outcomes through solid execution: clear goals, milestone planning, risk management, and crisp accountability.
Build durable cross-org partnerships with adjacent platform and experience teams (clients, identity, policy, compliance, data, AI platform, etc.).
Establish quality and evaluation discipline: guardrails, success metrics, offline evaluation, online experimentation, and regression detection.
Own operational excellence: reliability, latency, incident readiness, and continuous improvement through observability and automation.
Recruit, retain, and develop talent, cultivating an inclusive culture and coaching leaders across the org.

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