Customer Success Manager II

About the Role

Calendly is seeking an experienced Customer Success Manager II to join our growing Customer Experience team. This is a high-impact opportunity to work with millions of users who rely on Calendly daily. You'll manage a diverse, high-volume portfolio of 200+ accounts within the scaled segment, driving product adoption, renewals, and expansion opportunities. Reporting to the Senior Manager of Customer Success, you'll be responsible for delivering exceptional customer experiences at scale while collaborating cross-functionally with Sales, Product, and Support teams to influence product direction and elevate the customer voice.

What You'll Do Day-to-Day

• Portfolio Management: Manage a high-volume, diverse portfolio of 200+ accounts within the scaled segment, balancing operational efficiency with personalized customer engagement tailored to each account's unique needs.
• Drive Renewals: Own renewals as a core priority, leveraging usage data, automation, and strategic insights to efficiently assess risk and renewal likelihood across your entire book of business.
• Identify Expansion Opportunities: Navigate complex customer environments to uncover expansion opportunities across multiple business units and stakeholders, maximizing customer lifetime value.
• Deliver Scalable Experiences: Build and execute a consistent, scalable customer experience by leveraging playbooks, automation, and data signals to proactively identify at-risk accounts and growth opportunities.
• Cross-Functional Collaboration: Work seamlessly with Sales, Product, and Support teams to advocate for customer needs, provide valuable feedback, and help shape product roadmap decisions.
• Data-Driven Strategy: Analyze customer data and usage patterns to drive strategic outcomes, uncover engagement trends, and inform proactive outreach and intervention strategies.

What We Need From You

• Experience: 2-3+ years in Customer Success, Account Management, Renewals, or Sales within a SaaS or Product-Led Growth (PLG) environment.
• Renewal Track Record: Proven success owning and driving renewals across a high-volume book of business, with demonstrated experience supporting customers with multi-team or multi-product usage patterns.
• Data Analysis Skills: Strong ability to analyze customer data, identify actionable trends, and use insights to drive strategic outcomes and customer engagement decisions.
• Technical Proficiency: Confident working with industry-standard tools including Salesforce, Gainsight, DocuSign, and other Customer Success systems. Committed to maintaining accurate, up-to-date records across a high-volume portfolio.
• Independence & Collaboration: Capable of working independently on most customer scenarios while collaborating effectively with cross-functional teams and contributing to team best practices and process improvements.
• Customer-Centric Mindset: Proactive, growth-oriented approach with genuine passion for helping customers derive maximum value from Calendly and achieve their business goals.
• Communication Skills: Excellent written and verbal communication abilities, with the capacity to engage stakeholders at all organizational levels.

Why Join Calendly's Customer Experience Team?

At Calendly, we're committed to providing a high-touch experience to every customer, enabling them to maximize our product and reclaim valuable time in their daily lives. Our Customer Experience team is at the heart of this mission. You'll join a talented group of professionals dedicated to customer success, working with a product used by millions globally. This is an exciting time for Calendly—we're experiencing significant product growth and expansion. As a CSM II, you'll accelerate your career, working alongside some of the best people in the industry, learning continuously, and doing the best work of your professional life.

The role offers remote flexibility, allowing you to manage your portfolio and collaborate with global teams from anywhere. You'll have access to world-class training, career development opportunities, and the chance to directly influence how we serve our customers.

Key Competencies

Success in this role requires strong organizational skills, the ability to manage competing priorities, comfort with ambiguity, and a results-oriented mindset. You should be comfortable with quantitative analysis, have strong written and verbal communication abilities, and demonstrate genuine curiosity about customer needs and business drivers. The ideal candidate is self-motivated, resilient, and thrives in a fast-paced, collaborative environment.

💰 Compensation not publicly listed. Market estimate for similar roles: from $70K, varying by experience and location.