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Senior Technical Project Manager

  • Remote
  • Engineering

What is Calendly?

Calendly takes the work out of scheduling so our customers have more time to work on what’s really important. Our software is used by millions of people worldwide—with thousands more signing up every day. To maintain this exciting growth, we’re looking for top talent to join our team and help shape the future of our product.

Why join Calendly’s Engineering team? 

The Core Group consists of 8 squads and is responsible for Calendly's core product capabilities of scheduling and meeting management. As a Senior Technical Project Manager (TPM) in the Core Group, you will be expected to seamlessly shift between different altitudes - from working directly with the squads one moment, to collaborating with R&D leadership around driving high priority initiatives the next. You will work with a cross-functional squad (engineering, product, UI/UX, QE, research, etc) to efficiently prioritize, track, and deliver new features. You will work closely with other Core Group TPMs to report on project progress to convey the health of each initiative. This role is within the Engineering department, and reports to the Senior Manager, Technical Project Management.

Our ideal candidate is a clear communicator who is exceedingly detail oriented, continually looks for opportunities to automate and has excellent knowledge of project management best practices as applied in an agile environment. Candidates should be proactive problem solvers that are comfortable asking probing questions and engaging in technical and business discussions. Most importantly, they are eager to overcome challenges of scale by motivating the team to work together in the most efficient manner by utilizing their strong interpersonal skills to influence without authority. 

What are some of the high impact opportunities you’ll tackle? 

  • Program manage Core Group initiatives - including progress tracking and reporting of status, dependencies, milestones, and risks
  • Collaborate with Product & Engineering leaders to drive strategic R&D OKRs
  • Identify opportunities to automate processes, frameworks, and workflows - and ensure those are defined, documented, and adopted 
  • Mentor TPMs and raise the overall maturity of the TPM department
  • Facilitate Agile ceremonies (standup, backlog refinement, estimation, sprint planning, retrospective) and applying appropriate project management methodology to successfully drive delivery (Scrum, Kanban, or a hybrid)

This opportunity is for you if you have/are:

  • 8+ years experience in software delivery (ideally B2B SaaS organizations)
  • 8+ years project/program management experience in an agile environment
  • Results-oriented - stays highly organized and multi-tasks while maintaining attention to detail, influence across the organization, and exercise high judgment for trade-offs
  • Experience automating manual processes to increase Engineering productivity
  • Agile (CSM, ACP) and/or project management (PMP) certifications
  • Experience with Atlassian suite (Jira, Confluence, Trello), Aha!, Google suite, Miro, Slack
  • Previous startup experience and an unwavering passion and ability to flex to the scope required based on the business needs
  • Experience managing projects with teams across different geographic locations
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at

This specific role is not eligible for employment in California, Hawaii, or Alaska. Note that all individual roles will specify location eligibility.

Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection