Senior Technical Program Manager

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 systems performance, end user experiences with clear key performance indicators - Demonstrated impact leading multi-quarter initiatives across several teams with complex dependencies; track record of improving delivery predictability and quality - Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time Technical & Process Expertise - Deep understanding of SDLC and Agile at scale; expertise building integrated plans with milestones, dependencies, and objective delivery checkpoints - Experience with cloud-native environments and modern CI/CD practices; familiarity with reliability/incident management and security/compliance considerations (e.g., SOC 2, ISO 27001) - Proficiency with program tooling (e.g., Jira, Confluence, or similar) and creating source-of-truth artifacts (roadmaps, RACI, decision logs, status dashboards) Leadership & Communication - Strong cross-organizational influence and stakeholder management; excellent communication that scales from engineers to executives - Data-driven approach; skilled at defining program KPIs/OKRs and distilling complex data into actionable insights and clear executive narratives Nice to Have - Prior hands-on engineering background - Experience in platform modernization, privacy/data programs, or large-scale cross functional engineering programs at the intersection of infrastructure, data platform and the core SaaS products