Senior Strategic Customer Success Manager

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.

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.

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.

• 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

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. 

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