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.

Senior Strategic Customer Success Manager

Key skills