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Calendly · 19 hours ago

Senior Technical Program Manager

United States

Full-time

Remote

Senior Level, Lead/Staff

8+ years exp

Calendly is a company focused on innovation within its Engineering team, and they are seeking a Senior Technical Program Manager to lead complex, cross-functional engineering initiatives. The role involves driving clarity and alignment across teams while managing the delivery of multi-team engineering programs and ensuring operational excellence.

CollaborationEnterprise SoftwareMeeting SoftwareProductivity ToolsSchedulingSoftware

No H1B

Responsibilities

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

Qualification

Technical Program ManagementSDLCAgileCloud-native environmentsCI/CD practicesProgram tooling JiraProgram tooling ConfluenceStakeholder managementData-driven approachCommunication skills

Required

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

Preferred

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