Senior Technical Program Manager

What’s in it for you?

Ready to make a serious impact? Millions of people already rely on Calendly, and we're still in the midst of exciting product growth — it's a fantastic time to join us. Everything you'll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you've ever worked with, then we hope you'll consider allowing Calendly to be a part of your professional journey.

About the Team & Opportunity

What's so great about working on Calendly's Engineering team? We make things possible for our customers through innovation.

We're seeking an exceptional Technical Program Manager (TPM) to orchestrate complex, cross-functional engineering initiatives across our infrastructure, data, and product engineering teams. You'll be driving clarity, alignment, and sharp execution with clear outcomes across the organization.

A Day in the Life of a Technical Program Manager

Strategic Program Leadership

• Lead end-to-end delivery of complex, multi-team engineering programs from problem definition to delivering clear outcomes; align stakeholders on vision, outcomes, and measurable success criteria

• Build integrated program roadmaps and dependency frameworks; manage critical paths across squads and proactively sequence work for predictable delivery

• Contribute to capacity alignment across teams; balance long-term platform investments with near-term business priorities and outcomes.

Execution & Operational Excellence

• Establish operating rhythms (kickoffs, status reviews, risk/issue forums, and executive readouts) that drive transparency, fast decision-making, and accountability

• Identify risks and systemic blockers early; drive mitigation and tradeoff decisions with data, options, and clear recommendations

• Partner with Infrastructure, Data Platform, Product and engineering on discovery and scope management; High-quality delivery and impact with appropriate change management

Technical Rigor & Continuous Improvement

• Facilitate cross-team technical alignment and engineering reviews; ensure architectural decisions consider long-term scalability, reliability, security, and maintainability

• Define and monitor program health metrics (delivery predictability, cycle time, production defect escape, availability/SLO adherence); facilitate blameless retros and continuous improvement

• Guide incident response for critical cross functional engineering programs and lead post-incident reviews; translate learnings into durable process and tooling improvements

Culture & Impact

• Coach teams and TPM peers on program best practices; raise the bar on communication quality, crisp execution, and outcome orientation

What We Need From You

Experience & Track Record

8–10+ years of technical program management experience within Infrastructure, Data and product engineering organizations, delivering large-scale, cross-functional outcomes, driving syst