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Senior Director, Customer Support

July 31, 2026

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.

Summary

The Senior Director, Customer Support is a senior leader responsible for shaping and executing the vision, strategy, and operations of the customer support function. This individual oversees all aspects of customer support delivery, ensuring an exceptional, consistent, and scalable customer experience. The Senior Director leads and develops high-performing teams, partners cross-functionally with Customer Success, Product, and Engineering, and uses data to drive continual improvement in support processes, customer satisfaction, and operational efficiency.

Key Responsibilities

Develop and execute a customer support strategy aligned with company goals, prioritizing customer satisfaction, retention, and operational excellence.
Lead, mentor, and scale customer support teams, fostering a culture centered on collaboration, accountability, and continuous improvement.
Oversee daily operations across support channels, including email, chat, phone, and in-app support, ensuring timely resolution and high-quality interactions.
Establish, monitor, and report on support metrics and KPIs, such as response times, CSAT, NPS, ticket backlog, and escalation rates.
Collaborate with cross-functional partners, including Customer Success, Product, Engineering, and Sales, to champion the voice of the customer and drive enhancements to the product and support experience.
Analyze support data and customer feedback to identify trends, root causes, and opportunities for process or product improvement.
Design and optimize workflows, tools, and knowledge resources to support scalability as the customer base grows.
Oversee training and development programs, ensuring team members have the knowledge and skills to deliver excellent support.
Manage support budgets, resource planning, and vendor relationships as needed.
Handle escalated customer issues and critical incidents, ensuring prompt resolution and appropriate communication with stakeholders.
Partner cross-functionally to drive initiatives focused on automation, self-service, and proactive support that reduce friction and enhance customer value.

Required Qualifications

Bachelor's degree or equivalent work experience.
8+ years of experience in customer support or customer service roles, including 3+ years of people management at the manager, director, or senior director level.
Proven track record of building, leading, and scaling customer support teams in SaaS, technology, or fast-paced environments.
Demonstrated success with operational excellence, using metrics, data, and customer insights to inform strategy and improvements.
Experience with customer support technology platforms, including CRM, ticketing, chat, and analytics tools such as Zendesk, Salesforce Service Cloud, or Intercom.
Strong leadership, communication, and interpersonal skills, with the ability to inspire and develop teams.

Preferred Skills and Qualifications

Advanced degree, such as an MBA, relevant certification, or training in customer experience, contact center management, or operations.
Experience managing global or distributed teams.
Change management expertise and a track record of leading through organizational transformation.
Experience designing or scaling automation and self-service tools, such as knowledge bases and chatbots.
Familiarity with customer-centric methodologies, including Voice of the Customer, Design Thinking, and Lean or Agile support practices.
Ability to influence and work cross-functionally to drive business outcomes.

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.

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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...