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Senior Manager, Customer Success

  • 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 and help shape the future of our product. 

Why join Calendly’s Customer Experience team? 

For you it’s not just the role; it’s the people, culture, and values. We get it! 

Like you, we pride ourselves on the success of our customers and fostering value-driven relationships. You crave a team that works and plays hard - that’s just as customer centric, ambitious, and committed to collaboration as you are. 

In this role, you will be responsible for building and scaling the Mid Market Customer Success function reporting directly to the Head of Customer Success. You’ll oversee a growing team of two managers and their 15+ CSMs and partner closely with other Senior Managers and business partners to scale our operational efficiency, implement new processes to accelerate our progress towards retention goals, and continuously improve our team. 

You’ll be joining us at a pivotal stage of growth as our team rapidly expands and you’ll play a key part in developing best practices, processes, and infrastructure. 

Some challenges you’ll get to tackle:

  • Recruit, train, and lead a high performing Customer Success team responsible for account heath and ARR retention.
    • Create an environment where people love coming to work
    • Assist with Manager and team onboarding and furthering their development
    • Host 1:1’s, team meetings, performance and other conversations 
    • Measure and ensure team effectiveness and quality customer outcomes
  • Engage with Customers 
    • Develop executive relationships with our most strategic accounts by joining calls weekly, in partnership with your team and other stakeholders
    • Be the escalation point for Managers, as needed escalate to the Head of CS 
  • Focus on Results
    • Track and analyze portfolio stats to meet and exceed KPI’s on account health and ARR retention.
    • Providing accurate ARR forecasting to CS/CX leadership
    • Driving continuous improvement through updating internal processes and implementing best practices in the below areas:
      • Business Review development and delivery
      • How CSMs lead customers to realize maximum value
      • Overall customer success strategy as the function evolves
  • Partner for Success Internally with: 
    • Peers in Customer Success Management
    • The Sales organization to drive account strategy alignment, focused on mutually desired business objectives
    • Customer Programs, Support, Marketing, Product, etc to increase internal customer advocacy

This opportunity is for you if:

  • You have a proven track-record of developing front line Managers and ICs of Customer Success in a remote-first environment. 
    • 5+ years experience leading SaaS Customer Success teams predominantly leading Managers; may also manage senior ICs
    • 7+ years experience in a SaaS Customer Success role managing a multi-million dollar portfolio supporting Mid-Market and/or Enterprise segments, consistently achieving goals
  • You bring a process-oriented approach. You have an eye for detail and data, and are always looking for ways to optimize and innovate.
    • Owner's mindset required, you’re ready to lead your portfolio and team to success 
    • An aptitude for fast and agile learning - a strong business acumen with the ability to quickly analyze problems and identify solutions 
    • Demonstrate determination in getting to the bottom of complex issues
  • You genuinely care 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 to a wide variety of customers at various levels
  • Passionate about quant and qual data and love deriving insights, showing strong analytical experience
    • Experience using Salesforce to manage renewals and forecasting; you must be able to build reporting and dashboards
    • Tech Stack: Vitally, Gainsight, Gong, Mode, Salesforce
  • 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.

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