Remote Senior Customer Success Manager @ Calendly

About the team & opportunity 

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

We provide a high touch experience to each customer and enable them to maximize our product so that they can gain valuable time back into their day to day.

Why do we need you?

Well, we are looking for a Senior Customer Success Manager who will bring strategic thinking, a proactive mindset, and experience with scaled customer engagement. You will report to the Manager, Customer Success and will be responsible for managing a strategic portfolio of customers, driving adoption, retention, and long-term growth within our Growth segment.

A day in the life of a Senior CSM at Calendly.

On a typical day, you will be working on:

• Managing a diverse portfolio of high-potential ($10K–$60K ARR) customers in the Growth segment.
• Leveraging product usage data and risk signals to inform proactive engagement strategies.
• Driving product adoption, renewals, and expansion by aligning Calendly solutions to customer goals.
• Leading complex account planning and tailoring ROI narratives for strategic customers.
• Collaborating cross-functionally with Sales, Product, Marketing, and Solutions Architecture to advocate for customer needs and influence internal strategy.
• Building strong relationships across customer organizations, including C-suite and key decision-makers.
• Contributing to internal initiatives that improve Customer Success processes, tools, and scalability.

What do we need from you?

• 4+ years of experience in Customer Success or Account Management in SaaS, with 2+ years in a strategic or senior role.
• Experience managing complex customer portfolios and driving value through consultative approaches.
• Proficiency with tools like Salesforce, Gainsight, and Slack; strong internal communication and documentation habits.
• Strong cross-functional collaboration skills and ability to influence product and go-to-market strategies.
• Comfort operating with independent discretion and navigating ambiguity in a fast-paced environment.
• Strong business acumen and communication skills across both technical and executive audiences.
• 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, Alabama, Delaware, Hawaii, Idaho, Montana, North Dakota, South Dakota, Nebraska, Iowa, West Virginia, and Rhode Island, 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$137,700—$186,300 USDTier 2 Salary$126,225—$170,775 USDTier 3 Salary$114,750—$155,250 USD