Head of Product Operations

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What Calendly is looking for in applicants

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 Product Operations team? 

We’re looking for an experienced product operations leader to help grow and scale the product operations function here at Calendly.

Calendly is growing and scaling at a rapid pace, and as Head of Product Operations, you will be responsible for helping to ensure that we have the right processes in place to continuously deliver high quality product experiences for our customers and outcomes for the business.  

In this role, you will lead a team of Product Operations Managers who are passionate about continuous improvement to the product development process, cross-functional communication, and providing visibility to both internal and external stakeholders around the product roadmap. 

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

  • Execution
    • Annual/quarterly roadmap planning
    • Product, design, and release readiness reviews
    • Post release success tracking and retrospectives
    • Sunsetting evaluation 
    • Support the product leadership team in executing our product strategy and driving cross-functional initiatives
    • Build, launch, and manage the system of operations for Calendly’s product development organization
    • Own and continuously improve the Product Development Lifecycle to remove bottlenecks, streamline communication, and help us focus and most faster 
    • Create a clear and consistent process for routing customer feedback into the product development process
    • Craft a predictable release readiness process that ensures consistent delivery of high-quality product experiences for customers through standardization of rollout phases and success metrics
  • Communication
    • Ensure internal and external customers have the right amount of advance communication, support, and lead time to utilize immediate value from a release
    • Create cross-company visibility into the product roadmap, upcoming launches, and post launch activities
    • Ensure cross-functional partners are aligned on key product objectives and collaborate with partner teams to prepare the org for upcoming launches  

This opportunity is for you if you have/are:

  • 10+ years in product leadership and/or product operations roles
  • Direct people management experience
  • Expert in best practices in product management, product design, and product operations
  • Demonstrated success in company-wide alignment and change management
  • Ability to partner and align with stakeholders across the business such as Marketing, Sales, Support, and Customer Success 
  • 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

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.

Want some tips on how to get an interview at Calendly?

What is Calendly looking for?
If this role looks interesting to you, a great first step is to understand what excites you about the team, product or mission. Take your time thinking about this and then tell the team! Get in touch and communicate that passion.
What are interviews for Head of Product Operations like?
Interview processes vary by company, role and team. The best plan is to see what others have experienced and then plan accordingly.
How to land an interview at Head of Product Operations?
A great first step is organizing your path to an offer. Check out Kiter for tools to get started!