Senior Manager of Customer Success

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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. 

Our Customer Success organization will grow 3x in 2022 as we expand to support Mid Market, Enterprise, and our named account strategy. Join our team and play an active role in our growth, seeing the impact of your work as you lead CSMs supporting our largest customers and driving collaboration and operational excellence across Calendly.

Why join Calendly’s Customer Success team? 

We are looking for a proven leader capable of building, scaling & inspiring, a world-class Customer Success team. In this role as a key leader of the broader Customer Success department, you’ll build and lead a team of CSMs responsible for supporting our largest customers and strategic named accounts from onboarding to renewal.

You’ll operate as the CEO of your portfolio owning all aspects from: day to day operations, team coaching, and driving business OKRs forward. Your main priority will be increasing retention followed by adoption, and the overall health of your portfolio. 

Your team will look to you for guidance to help them reach their goals and grow in their careers. You will communicate openly and regularly with your team members about their performance, aspirations, and well-being. 

Some challenges you’ll get to tackle:

  • Building and leading a high performing Customer Success team that:
    • Embodies a WE-vs-ME mindset and lives the Calendly values.
    • Thrives working autonomously yet values learning and winning together. 
    • Leads with consultative and solution-based techniques.
  • Own your portfolio by being accountable for portfolio usage and ARR retention and health
    • Developing the long-term vision and strategy for the team and manage day-to-day operations
    • Measuring team effectiveness by clearly defining operational outcomes and creating a cadence for review with the team
    • Tracking and analyzing portfolio statistics based on key quantitative metrics
    • Providing accurate weekly/monthly ARR forecasting to leadership
    • Carry out managerial responsibilities such as 1:1’s, weekly updates, performance and growth conversations etc. 
  • Driving continuous improvement through updating internal processes and implementing best practices in the below areas:
    • CSM onboarding and furthering development
    • Business Review development and delivery
    • How CSMs lead customers to realize maximum business value
    • Overall customer success strategy as the function evolves
  • Partnering with the Sales organization to drive account strategy alignment, focused on mutually desired business objectives
  • Developing direct executive relationships with our most strategic accounts by joining calls weekly, in partnership with your team and other stakeholders
  • Coaching and mentoring other managers in the broader Success organization
  • Driving internal customer advocacy throughout Calendly with internal teams such as Sales, Support, Marketing and Product.

This opportunity is for you if you have/are:

  • 4+ years of experience leading an Enterprise/Strategic Customer Success team to achieve operational and financial KPIs and CSAT/NPS and have an operational excellence mindset
  • 5+ years of experience in a Customer Success Manager role managing a multi-million dollar book of business supporting Mid-Market and/or Enterprise segments, consistently achieving goals, and driving true customer ROI. 
  • An owner's mindset and are ready to lead your portfolio and team to success. 
  • Care deeply, genuinely and passionately about the CSM role and about the role it plays in making a customer centric company successful.
  • High positive energy, self awareness, impeccable time management skills, and an ability to self-direct.
  • Excellent interpersonal, customer service and communication skills to comfortably interact and explain complex problems succinctly and clearly a wide variety of customers at various levels.
  • An aptitude for fast and agile learning - a strong business acumen with the ability to quickly analyze problems and identify solutions
  • Are adaptable to the changing needs of our customers, CSMs, and business, and the evolving responsibilities to address those needs
  • Experience using Salesforce to manage renewals and forecasting; you must be able to build reporting and dashboards
  • Strong track record of defining and executing against key performance indicators.
  • Excellent organization, project management and time management skills.
  • Passionate about data and love deriving insights, showing strong analytical experience
  • Demonstrate determination in getting to the bottom of complex issues
  • US Citizenship or Permanent Residency (we do not sponsor 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.

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 Senior Manager of Customer Success 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 Senior Manager of Customer Success?
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