Senior Strategic Customer Success Manager

Details

• 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.
• 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
• Tier 1: San Francisco, CA, San Jose, CA, New York City, NY
• Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA.
• Tier 3: All other locations not in Tier 1 or Tier 2
• Tier 1: San Francisco, CA, San Jose, CA, New York City, NY
• Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA.
• Tier 3: All other locations not in Tier 1 or Tier 2