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Head of User 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 Head of User Experience to help take our product to the next level of excellence in user centered design. Calendly is the world’s best way to schedule the meetings that matter most to a professional or a business and to share your availability as quickly and efficiently as possible. You will be in charge of building and evolving all the work that contributes to being the best user experience for this purpose in the world. Your responsibilities will include evolving and maturing our design and content strategy practices and helping take them to the next level, working with all the talented people we have. You will make sure that we have stringent standards to accomplish our ‘simple’ strategy and there is upward continuous evolution and a culture of excellence. You will also be expected to use your creativity and drive to contribute to our product vision and execution as you manage and partner with seasoned designers and content strategists to build impactful user centered products.

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

  • Build, mentor, and lead a world-class team of designers and content strategists while creating and evolving the ideal organizational design
  • Establish the standards, practices and processes that take Calendly to a world class user experience company that is reflected in consistently delivering user centered software to customers
  • Guiding conceptual designs through to launch and optimizing post-launch for positive end-user feedback & adoption
  • Build and drive a strong user research and usability testing practice that uses a range of qualitative and quantitative data to inform user experience strategy
  • Ensure UX teams are “set up for success” in the execution of both roadmap and advanced concepting initiatives and sprints
  • Manage executive and stakeholder alignment to drive a common UX vision that supports the Product Roadmap
  • Evolve and strengthen a world-class user experience and design culture that is inspiring, innovative, supportive, growth-oriented
  • Recruit, nurture and retain top-tier talent
  • 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:

  • 12-15+ years of experience designing and delivering user-centered, engaging software-driven experiences across a range of platforms and can demonstrate the success and impact of your efforts for both users and business
  • Significant expertise in user research and usability practices that help discover opportunities and address customer adoption problems before products are shipped
  • 7+ years of management experience, including experience leading large design and user research teams of 15+ people within a cross functional organization
  • A leader who people want to follow; You build trust, inspire, and mentor designers and design managers
  • A leader who possesses deep knowledge of user-centered design methods and customer discovery and research practices
  • Experience working in design systems, and a highly refined visual design sensibility
  • A great communicator (verbal, written, and visual) who has the ability to influence and build consensus both within a UX team and with executive stakeholders across the company
  • An exceptional partner and collaborator who builds strong relationships with partners across functions
  • An understanding that great user experiences add value both for our customers and our business, and you are able to integrate business requirements into user experience strategy and processes.
  • Experience in modern B2B SaaS software is a key requirement
  • BA/BS and/or MA/MS in a relevant design field
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

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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