Senior Technical Program Manager, Calendly

• 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
• 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)
• 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

Desirable

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