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

Requirements

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

Benefits

Top Performer Bonus program (or Sales incentive)
Equity awards
Competitive benefits

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills

technical program managementSDLCAgilecloud-native environmentsCI/CD practicesreliability managementincident managementsecurity complianceprogram KPIsOKRs

Soft skills

cross-organizational influencestakeholder managementcommunicationcoachingproblem-solvingdecision-makingaccountabilitytransparencycontinuous improvementoutcome orientation

Certifications

SOC 2ISO 27001