Senior Director, Customer Support

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.

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.

• 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.

• 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.

• 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.

• Familiar…