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Senior Strategic Customer Success Manager

134k – 189kUnited StatesRemote5+ YOE
Summary

Owns a portfolio of Calendly's highest-value accounts, driving adoption, retention, and expansion while serving as a strategic advisor to executive stakeholders. Requires 5+ years of SaaS customer success or account management experience managing complex enterprise accounts.

About the role

Responsibilities

  • Manage a diverse portfolio of Calendly’s largest accounts ($40k+ ARR), leading with strategic plans that ensure adoption, retention, and long-term growth
  • Understand and navigate complex customer environments to uncover expansion opportunities across multiple business units and stakeholders
  • Deliver a white-glove experience by proactively identifying & mitigating risk and opportunities, fostering executive engagement, and building long-term roadmaps that demonstrate measurable ROI
  • Act as a strategic partner by aligning Calendly’s product with customer business objectives, leveraging advanced configurations, integrations, and use cases
  • Collaborate cross-functionally with Sales, Product, and Support to elevate the customer voice and influence product direction
  • Play a leadership role in CS operations by contributing to process evolution, playbook development, and CS-wide initiatives
  • Confidently represent Customer Success across internal and external forums

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
Skills
SalesforceGainsightCustomer SuccessAccount ManagementSaaSEnterprise Account ManagementData AnalysisCross-functional CollaborationStrategic PlanningROI Analysis
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