Senior Customer Success Manager

Summary

Join Calendly's Customer Experience team as a Senior Customer Success Manager and manage a portfolio of high-potential customers, driving adoption, retention, and growth. Leverage data to inform engagement strategies, align Calendly solutions with customer goals, and lead complex account planning. Collaborate cross-functionally to advocate for customer needs and contribute to internal initiatives. This role requires 4+ years of experience in Customer Success or Account Management in SaaS, with 2+ years in a strategic or senior role. Proficiency with Salesforce, Gainsight, and Slack is necessary. Calendly offers a competitive total rewards package including base salary, quarterly corporate bonus program or sales incentive, equity awards, and benefits.

Requirements

• 4+ years of experience in Customer Success or Account Management in SaaS, with 2+ years in a strategic or senior role
• Experience managing complex customer portfolios and driving value through consultative approaches
• Proficiency with tools like Salesforce, Gainsight, and Slack; strong internal communication and documentation habits
• Strong cross-functional collaboration skills and ability to influence product and go-to-market strategies
• Comfort operating with independent discretion and navigating ambiguity in a fast-paced environment
• Strong business acumen and communication skills across both technical and executive audiences
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Responsibilities

• Managing a diverse portfolio of high-potential ($10K–$60K ARR) customers in the Growth segment
• Leveraging product usage data and risk signals to inform proactive engagement strategies
• Driving product adoption, renewals, and expansion by aligning Calendly solutions to customer goals
• Leading complex account planning and tailoring ROI narratives for strategic customers
• Collaborating cross-functionally with Sales, Product, Marketing, and Solutions Architecture to advocate for customer needs and influence internal strategy
• Building strong relationships across customer organizations, including C-suite and key decision-makers
• Contributing to internal initiatives that improve Customer Success processes, tools, and scalability

Benefits

• Quarterly Corporate Bonus program (or Sales incentive)
• Equity awards
• Competitive benefits