Customer Success Manager II

September 15, 2026

Other Jobs To Apply

No other job posts for this day.

What’s in it for you?

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — 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.

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 Customer Success Manager II who will bring a proactive, growth-oriented mindset and a passion for helping customers get real value out of Calendly. You'll report to the Senior Manager, Customer Success and will be responsible for managing a high-volume portfolio of accounts, driving product adoption, and owning renewals — using your product knowledge, data, and playbooks to engage the right customers at the right time.

A day in the life of a CSM at Calendly.

On a typical day, you will be working on:

Manage a high-volume, diverse portfolio of 200+ accounts within the scaled segment, balancing efficiency with personalized customer engagement.
Drive renewals as a core priority, using usage data and automation to efficiently assess risk and likelihood to renew across a large book of business.
Understanding and navigating complex customer environments to uncover expansion opportunities across multiple business units and stakeholders.
Deliver a consistent, scalable customer experience across a high-volume portfolio by leveraging playbooks, automation, and data signals to proactively identify risk and expansion opportunities.
Collaborating cross-functionally with Sales, Product, and Support to elevate the customer voice and influence product direction.

What do we need from you?

2-3+ years of experience in Customer Success, Account Management, Renewals, or Sales within a SaaS/PLG environment.
Proven track record of owning and driving renewals across a high-volume book of business, with experience supporting customers who have multi-team or multi-product usage.
Skilled in analyzing customer data to drive strategic outcomes and uncover trends that inform proactive engagement.
Confident with tools like Salesforce, Gainsight, DocuSign, and other CS systems; dedicated to keeping internal systems up-to-date and accurate across a high-volume book of business.
Able to work independently on most customer scenarios, collaborate effectively with cross-functional teams, and contribute to team best practices and process improvements
Excellent communicator with strong business acumen and a sharp eye for balancing customer satisfaction and company goals.
Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Tier 1 Salary Hiring Range

$95,605—$109,262 USD

Tier 2 Salary Hiring Range

$87,638—$100,157 USD

Tier 3 Salary Hiring Range

$79,670—$91,052 USD

The ranges listed above 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 equity awards, and competitive benefits. Eligible Sales employees also qualify for a Sales Incentive program.

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

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 let your Recruiter know when first connecting with them. Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Delaware, Hawaii, Idaho, Iowa, Montana, Nebraska, North Dakota, Rhode Island, South Dakota, 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

This role may require occasional travel for company events, team collaboration, or offsites.

Compensation (from employer):
Tier 1 Salary Hiring Range — 95,605 – 109,262 USD
Tier 2 Salary Hiring Range — 87,638 – 100,157 USD
Tier 3 Salary Hiring Range — 79,670 – 91,052 USD

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...