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Senior Strategic Customer Success Manager job at Calendly in US National (Not hiring in SD, MT, AK, AL, WV, DE, NE, RI, ID, IA, ND, HI)

July 29, 2026

Title: Senior Customer Success Manager Location: Remote Job Description: 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 Senior Strategic Customer Success Manager who will bring a proactive, growth-oriented mindset, deep cross-functional collaboration skills, and the ability to deliver long-term impact to customers. You will report to the Manager, Customer Success and will be responsible for owning a portfolio of our most complex, highest-value accounts, driving adoption, retention, and expansion, and serving as a strategic advisor to executive-level stakeholders. A day in the life of a Senior Strategic CSM at Calendly On a typical day, you will be working on: Managing a diverse portfolio of Calendly’s largest accounts ($40k + ARR) leading with strategic plans that ensure adoption, retention, and long-term growth. Understanding and navigating complex customer environments to uncover expansion opportunities across multiple business units and stakeholders. Delivering a white-glove experience by proactively identifying & mitigating risk and opportunities, fostering executive engagement, and building long-term roadmaps that demonstrate measurable ROI. Acting as a strategic partner by aligning Calendly’s product with customer business objectives, leveraging advanced configurations, integrations, and use cases. Collaborating cross-functionally with Sales, Product, and Support to elevate the customer voice and influence product direction. Playing a leadership role in CS operations by contributing to process evolution, playbook development, and CS-wide initiatives. Confidently representing Customer Success across internal and external forums; building trust and alignment through strong communication and strategic thinking. What do we need from you? 5+ years of experience in Customer Success, Account Management, or Sales within a SaaS/PLG environment. Strong track record of owning and growing complex Enterprise accounts, especially those with multi-team and 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, and other CS systems; dedicated to keeping internal systems up-to-date and accurate. Demonstrated ability to operate autonomously, influence cross-functional decisions, and contribute to team growth and maturity. 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 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 Hiring Range $137,700 - $186,300 USD Tier 2 Salary Hiring Range $126,225 - $170,775 USD Tier 3 Salary Hiring Range $114,750 - $155,250 USD The ranges listed above are the expected annual base salary for this role, subject to change. Apply To this Job Company : Calendly Salary : Work from home

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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...