Customer Success Manager II

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?

We are looking for a Customer Success Manager II who will bring a proactive, growth-oriented mindset and a passion for helping customers get real value out of Calendly. You'll report to the Senior Manager, Customer Success and will be responsible for managing a high-volume portfolio of accounts, driving product adoption, and owning renewals — using your product knowledge, data, and playbooks to engage the right customers at the right time.

A day in the life of a CSM at Calendly

On a typical day, you will be working on:

• Manage a high-volume, diverse portfolio of 200+ accounts within the scaled segment, balancing efficiency with personalized customer engagement.
• Drive renewals as a core priority, using usage data and automation to efficiently assess risk and likelihood to renew across a large book of business.
• Understanding and navigating complex customer environments to uncover expansion opportunities across multiple business units and stakeholders.
• Deliver a consistent, scalable customer experience across a high-volume portfolio by leveraging playbooks, automation, and data signals to proactively identify risk and expansion opportunities.
• Collaborating cross-functionally with Sales, Product, and Support to elevate the customer voice and influence product direction.

What do we need from you?

• 2-3+ years of experience in Customer Success, Account Management, Renewals, or Sales within a SaaS/PLG environment.
• Proven track record of owning and driving renewals across a high-volume book of business, with experience supporting customers who have multi-team or 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, DocuSign, and other CS systems; dedicated to keeping internal systems up-to-date and accurate across a high-volume book of business.
• Able to work independently on most customer scenarios, collaborate effectively with cross-functional teams, and contribute to team best practices and process improvements
• 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