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Senior Customer Success Manager, Enterprise

  • Remote
  • Customer Experience

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 to drive value for our customers. 

Why join Calendly’s Customer Experience team? 

As we continue to expand in the Enterprise space we’re seeking a Senior Enterprise Customer Success Manager with 5+ years of experience serving Fortune 500 SaaS customers, who is ecstatic at the opportunity to be a part of our world class Customer Success organization at Calendly. 

You’ll be responsible for building effective relationships and maximizing the customer lifetime value within your portfolio of Calendly’s largest strategic accounts.  As our Senior Customer Success Manager you’ll own the full customer journey: onboarding of new customers, increasing adoption and overall health, navigating the renewal process, and assisting with customer growth by identifying add-ons and upsell opportunities.

To be successful in this role you’ll deliver an exceptional customer experience that exceeds expectations; you’ll focus on maximizing the use of our products and driving outcomes, results, and value. 

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

  • Primary ownership and accountability for meeting and exceeding  customer ARR retention,  satisfaction, and adoption targets within a portfolio of 100+ of Calendly’s largest strategic customers
  • Serve as an SME on Calendly’s offering and scheduling best practices to influence and guide your portfolios success
  • Use a consultative approach to develop a strategy and plan for achieving customer objectives 
  • Forge relationships with new customers, including management and executive stakeholders, and understand their objectives
  • Leverage new and existing tools, processes and best practices to ensure customers are realizing the greatest possible value from Calendly
  • Manage the full customer journey: 
    • Onboard customers in a timely and efficient manner by streamlining account configuration, sharing product and best practice guidance, hosting user/admin trainings, and other change management activities
    • Focus wisely to support ongoing successful adoption of Calendly’s products and to drive additional value throughout the lifetime of the subscription term to ensure renewal via periodic business reviews with customers
    • Own the renewal process leading strategic engagements that showcase progress on customer objectives and value delivered, and provide insights on industry trends, benchmarking, opportunities for additional value.
    • Partner with Sales Account Executives for strategic account planning, including customer renewals, add-ons and upgrades within your portfolio
  • Maintain impeccable administration of your accounts in our CRM
  • Coordinate with technical support for technically complex questions 
  • Drive cross-functional initiatives that will improve the overall customer experience and lead to greater satisfaction and loyalty among customers.

This opportunity is for you if you have/are:

  • Bachelor’s Degree or equivalent work experience and education preferred
  • 5+ years experience as an Enterprise or Senior CSM serving Fortune 500 companies in a SaaS environment
  • Embodies a WE-vs-ME mindset and embodies the Calendly values.
  • An owner's mindset and are ready to lead your portfolio to success 
  • Lead with positivity and have impeccable time management and organization skills
  • Possess the ability to self-direct and thrive with minimal supervision
  • Strong interpersonal, customer service and communication skills to comfortably interact and explain complex problems succinctly and clearly to a wide variety of customers at various levels
  • Ability to build a rapport through phone calls, email and video conferencing
  • Are resourceful and adaptable to the changing needs of our customers, and business, and the evolving responsibilities to address those needs
  • A passion for solving business problems with creativity and empathy
  • Experience with Salesforce or other CRM
  • Experience with Google Workspace Applications
  • 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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