What’s so great about working on Calendly’s Customer Experience team?

Every day, we have the privilege of serving our millions of users with the expertise and resources needed to ensure their success on the Calendly automated scheduling platform. Ensuring our customers gain valuable time back into their day to day is our #1 priority, and we are proud to be at their service.

Why do we need you? We are looking for a Head of Customer Education & Training who will bring adult learning principles, instructional design experience and digital-first, self-service enablement strategies to the team.  You will report directly to the Chief Customer Officer and will be responsible for the strategy and delivery of all our customer-facing, digital education properties including the Calendly Help Center, Community & Academy.

A day in the life of the Head of Customer Education & Training at Calendly

On a typical day, you will be working on:

  • Developing the vision, strategies and tactics that enable our customers to learn and adopt the Calendly platform at an ever increasing level of quality and operational scale
  • Leading a team to deliver self-service customer education, training & troubleshooting through the creation & delivery of written, video and interactive content, ensuring that we provide a world-class experience throughout the entire customer journey
  • Partnering with CX Operations team on the strategic direction & content of our AI chatbot
  • Owning our localization strategy, ensuring improvements to our experience for global customers
  • Leading the teams responsible for the Help Center, Community and Academy properties and programs
  • Creating and managing a feedback loop for content iterations coming from Support interactions to education properties to the product team and back
  • Mentoring and coaching your team members to encourage their own professional growth in combination with impactful outcomes for our customers
  • Partnering with the other leaders on the Customer Experience team in Support, Success & Operations to put the success of our customers first

What do we need from you?

  • 12+ years of work experience with 4+ years experience leading high-performing customer experience teams and 2+ years of experience as a second-line manager in the technology industry
  • Experience developing omni-channel customer education strategies and direct responsibility for running them across owned (ie. Help Center, Community) and 3rd party (ie. YouTube, Twitter) digital properties with a focus on scaling customer adoption, education & support
  • Experience evaluating, implementing and maintaining the applications that deliver customer education, including but not limited to Zendesk Guide, Ada, Insided, various LMS’s and rewards/gamification technologies
  • Strong desire to create high performing teams, with a passion for building excellent customer experiences
  • Ability to create, analyze and communicate the KPI’s associated with performance, with a focus on continuous improvement
  • Leadership in a fast-pace and ever-changing environment, where ambiguity fuels your curiosity, creativity and tenacity
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

What’s in it for you? 

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

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 recruiting@calendly.com . 

Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, California, Hawaii, Montana, North Dakota, South Dakota, Nebraska, Iowa, and West Virginia, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here

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

The ranges listed below are the expected annual base salary for this role, subject to change.

Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity.

Base salary is just one component of Calendly’s total rewards package. All full-time (30 hours/week) employees are also eligible for our Quarterly Corporate Bonus program (or Sales incentive), equity awards, and competitive benefits.

Calendly uses the zip code of an employee’s remote work location, or the onsite building location if hybrid, to determine which metropolitan pay range we use. Current geographic zones are as follows:

  • Tier 1: San Francisco, CA, San Jose, CA, New York City, NY
  • Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA.
  • Tier 3: All other locations not in Tier 1 or Tier 2
Tier 1 Salary
$173,400$234,600 USD
Tier 2 Salary
$159,000$215,100 USD
Tier 3 Salary
$144,500$195,500 USD
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