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Senior Product Manager, Checkout Experience

  • Remote
  • Product

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 team? 

Calendly is currently looking for a Senior Product Manager who will join our growing team to build on the success of the Calendly product - which is the best way to schedule the meetings that matter most to a professional or a business. 

As the Senior Product Manager, Checkout experience, you’ll create the vision, strategy, and roadmap to drive paid conversion and upgrades within the application. Specifically, you’ll focus on driving free users that have experienced Calendly’s value to convert. You’ll also focus on the upgrade, expansion, and downgrade experiences to drive revenue and CSAT. This will be a dynamic role, with high demands on multitasking, communication skills, and technical knowledge.

You will be working in an environment where collegial sparring is key to the best ideas, and you will also be expected to use your creativity and drive to bring new features and ideas to market. You will work closely with engineering, design, sales, product marketing, customer experience and product leadership to ensure the defined growth, product outcomes, and customer satisfaction goals are met. 

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

  • Defining the vision, strategy, and roadmap around the in-app consideration to purchase or consideration to product-qualified lead journeys, for product-led and sales-led conversion, respectively  
  • Rapid experimentation to drive conversions and upgrades
  • Partnering with our Customer Experience team to improve the downgrade experience, including gathering an understanding of why users downgrade and experimenting with programs to reduce downgrades
  • Collaborating cross-functionally with leadership, go-to-market teams, and other key stakeholders within the company
  • Staying up-to-date on the many ways our customers use Calendly to get their jobs done

This opportunity is for you if you have/are:

  • 7+ years of experience in Product Management
  • Previous experience monetizing modern B2C or B2B SaaS products, that has given you strong intuition around why users convert, upgrade, or churn
  • Top notch analytical skills to drive prioritization of feature builds and experiments
  • Keen product sense, UX design experience with a deep empathy for customers; highly motivated to ‘remove the pain’ and power a frictionless experience for customers
  • 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.