Customer Success Manager II
Job description
About the role
This role is for a Customer Success Manager II who will own a high-volume portfolio and drive adoption while shaping product direction. You will operate with autonomy within a fast-moving environment, balancing proactive outreach with data-driven decisions to create visible value for customers and the business. Reporting to a senior leader, you will manage complex accounts and translate insights into action.
About the Team and Opportunity
What makes Calendly's Customer Experience team distinctive is the focus on delivering a high-touch experience to each customer. The role exists to enable customers to maximize their use of Calendly, helping them reclaim valuable time in their daily workflows. We seek a proactive, growth-oriented professional passionate about helping customers extract real value from the product. You will work alongside talented peers while accelerating your own career through meaningful impact.
A Day in the Life
On a typical day, you will manage a high-volume, diverse portfolio of more than 200 accounts within scaled segments. Your work will balance efficiency with personalized engagement as you drive renewals and expansion. You will use usage data and automation to assess risk and opportunity across a large book of business. Navigating complex customer environments, you will uncover opportunities across multiple business units and stakeholders. By using playbooks, automation, and data signals, you will deliver a consistent and scalable customer experience. Collaboration with Sales, Product, and Support teams will ensure the customer voice influences product direction and internal decisions.
What We Need From You
- Bring 2-3+ years of experience in Customer Success, Account Management, Renewals, or Sales within a SaaS or PLG environment.
- Demonstrate a proven track record of owning and driving renewals across a high-volume portfolio, including accounts with multi-team or multi-product usage.
- Analyze customer data to identify trends and translate findings into proactive engagement strategies.
- Confidently use Salesforce, Gainsight, DocuSign, and other CS systems while maintaining strict accuracy for a large book of business.
- Work independently on diverse customer scenarios while collaborating effectively with cross-functional teams.
- Communicate clearly, balancing customer satisfaction with company goals and constraints.
- Be authorized to work lawfully in the United States of America, as Calendly does not engage in immigration sponsorship at this time.
Compensation and Location
Location is Remote within the United States. The compensation range reflects the expected annual base salary for this role and is subject to change.
- Tier 1 Salary Hiring Range: $95,605 to $109,262 USD
- Tier 2 Salary Hiring Range: $87,638 to $100,157 USD
- Tier 3 Salary Hiring Range: $79,670 to $91,052 USD
What You'll Do
- Guide expansion opportunities by mapping multiple business units and stakeholder needs.
- Design scalable customer journeys using playbooks, signals, and automation for a high-volume portfolio.
- Interpret usage patterns and data trends to prioritize accounts at risk or ready for growth.
- Coordinate with support, sales, and product teams to elevate customer feedback into action.
- Execute renewal strategies that combine insights, timing, and clear business value.
- Maintain system accuracy in Salesforce, Gainsight, and DocuSign for a large book of business.
- Build trusted relationships through consistent communication and clear outcome ownership.
- Partner with cross-functional groups to influence product decisions and customer success practices.
Requirements
- 2-3+ years of experience managing renewals and growth in SaaS or PLG environments.
- Ability to analyze customer data to uncover trends and translate findings into proactive engagement.
- Skill in navigating complex environments across teams and products to identify expansion potential.
- Proficiency with Salesforce, Gainsight, and DocuSign while ensuring records are accurate and current.
- Capability to work independently on diverse scenarios while collaborating effectively with teammates.
- Strong communication skills to balance customer satisfaction with company objectives and constraints.
- Authorization to work in the United States without sponsorship at this time.
Nice to Have
- Experience in scaled customer success operations with high touch and high volume accounts.
Skills and Tools
- Salesforce
- Gainsight
- DocuSign