Senior Strategic Customer Success Manager

Summary

Join Calendly's Customer Experience team as a Senior Strategic Customer Success Manager and make a significant impact on our growth. You will manage a portfolio of high-value accounts, driving adoption, retention, and expansion. This role requires proactive engagement, cross-functional collaboration, and strategic advising of executive-level stakeholders. A typical day involves managing complex accounts, identifying expansion opportunities, delivering exceptional customer experiences, and acting as a strategic partner. You will collaborate with Sales, Product, and Support teams, contribute to CS operations, and represent Customer Success internally and externally. Calendly offers competitive salaries and a chance to accelerate your career within a rapidly growing company.

Requirements

• 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

Responsibilities

• Managing a portfolio of Calendly’s largest accounts 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

Benefits

• Tier 1 Salary $137,700 — $186,300 USD
• Tier 2 Salary $126,225 — $170,775 USD
• Tier 3 Salary $114,750 — $155,250 USD