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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?

As a Technical Project Manager at Calendly, you will have the chance to collaborate across the organization on a variety of projects and high priority initiatives. You will support our engineering teams to efficiently prioritize, track, and deliver new features. You will work closely with our product, design, QA, marketing, customer success and business stakeholders to establish project KPIs and then report on progress to convey the health of each initiative. This role is within the Engineering department, and reports to the Manager, Technical Project Management.

Our ideal candidate is a clear communicator who is exceedingly detail oriented, continually seeks opportunities to improve, 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, engaging in technical and business discussions, and working with stakeholders. 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 organizational, interpersonal, and follow-through skills. 

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


  • Support up to 3 squads
  • Identify opportunities for improvement to processes and workflows - and ensure those are defined, documented, shared, and adopted 
  • Results-oriented - stay highly organized and multi-task while maintaining attention to detail, influence across the organization, and exercise high judgment for trade-offs


  • Technical aptitude - break down large projects into manageable pieces
  • Facilitating Agile ceremonies (standup, backlog refinement, estimation, sprint planning, retrospective) and applying appropriate project management methodology to successfully drive delivery (Scrum, Kanban, or a hybrid)
  • Assist in plan management, release management, and rollouts 

Communication and Collaboration

  • Build and maintain an open line of communication with stakeholders and team members in several departments (product, design, development, marketing, customer success, QA), and communicate details of upcoming and in progress projects
  • Follow up on cross-team dependencies and risks
  • Find creative ways to pitch in on the team by acting first and foremost as a servant leader; this is shown through creating a supportive environment, highlighting successes, promoting movement on conversations, connecting people, and positively influencing the team

This opportunity is for you if you have/are:

  • 5+ years experience in software delivery (ideally B2B SaaS organizations)
  • 5+ years project management experience in an agile environment
  • Experience managing up to 3 teams concurrently
  • Experience with continuous delivery development practices
  • Interest in building out the project management team at Calendly
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Bonus if you have experience with:

  • Agile (CSM, ACP) and/or project management (PMP) certifications
  • Experience with Atlassian suite (Jira, Confluence, Trello), Aha!, Google suite
  • 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
  • Four-year university/college degree in a business or technology related field

Calendly is registered as an employer in many, but not all, states. If you are not located in or able to work from a state where Calendly is registered, you will not be eligible for employment.


Not the right time to come onboard?

No problem! We’re all about making connections that make great things happen, so if the time’s not quite right for you to join us, but you’re keen to stay in the loop, just register your details, and we’ll add you to our talent pool.

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