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.
The 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 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 (email, chat, phone, in-app, etc.), ensuring timely resolution and high-quality interactions.
- Establish, monitor, and report on support metrics and KPIs (e.g., response times, CSAT, NPS, ticket backlog, escalation rates).
- Collaborate with cross-functional partners (Customer Success, Product, Engineering, 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.
- 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 or director level.
- Proven track record 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 (CRM, ticketing systems, chat, analytics tools—e.g., Zendesk, Salesforce Service Cloud, Intercom).
- Strong leadership, communication, and interpersonal skills with the ability to inspire and develop teams.
- Advanced degree (MBA or 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/self-service tools (e.g., knowledge bases, chatbots).
- Familiarity with customer-centric methodologies (e.g., Voice of the Customer, Design Thinking, Lean/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 our Top Performer 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
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.
Skills Required
- Bachelor's degree or equivalent work experience
- 8+ years of experience in customer support or customer service roles
- 3+ years of people management at the manager or director level
- Proven track record building, leading, and scaling customer support teams in SaaS or technology environments
- Demonstrated success using metrics, data, and customer insights to drive operational improvements
- Experience with customer support technology platforms (e.g., Zendesk, Salesforce Service Cloud, Intercom) and related CRM/ticketing/chat/analytics tools
- Strong leadership, communication, and interpersonal skills
- Advanced degree (MBA) or relevant certification or training in customer experience/contact center management
- Experience managing global or distributed teams
- Change management expertise and leading organizational transformation
- Experience designing or scaling automation and self-service tools (knowledge bases, chatbots)
- Familiarity with customer-centric methodologies (Voice of the Customer, Design Thinking, Lean/Agile support practices)
- Ability to influence cross-functionally to drive business outcomes
What We Do
At Calendly, we are excited about changing the way the world schedules. We are a profitable company, offering ample opportunities to accelerate your career. We’re obsessed with providing an elegant, delightful experience for our customers. This shapes how we develop, design, market and support. We work hard, move fast and pitch in across departments—and always make time to celebrate our accomplishments. Join a diverse workforce, leading the way in scheduling automation. Calendly, a powerful yet simple automated scheduling tool, takes the work out of connecting with others so you can accomplish more. Millions of users benefit from an enjoyable scheduling experience, more time to spend on top priorities and flexibility to accommodate individual users and large teams alike. Calendly works with Google, Office 365 and Outlook calendars and apps like Salesforce, Stripe, PayPal, Google Analytics, GoToMeeting and Zapier for a seamless user experience.
