[Remote] Senior Strategic Customer Success Manager

Note: The job is a remote job and is open to candidates in USA. Calendly is a rapidly growing company that provides scheduling solutions for millions of users. They are seeking a Senior Strategic Customer Success Manager to manage a portfolio of high-value accounts, driving adoption and retention while serving as a strategic advisor to executive-level stakeholders.

Responsibilities

• 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

Skills

• 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

Benefits

• Quarterly Corporate Bonus program (or Sales incentive)
• Equity awards
• Competitive benefits
• Top Performer Bonus program (or Sales incentive)
• Equity awards
• Competitive benefits
• Occasional travel for company events, team collaboration, or offsites

Company Overview