Customer Success Manager

About Us

We’re a startup with big ambitions: to make estate planning modern, visual, and intelligent. Vanilla is the first AI-powered estate advisory platform, built by advisors, planners, and attorneys to transform how wealth is transferred across generations. Our technology unifies scenario modeling, client visualization, and document creation into one seamless, digital experience.

Our team brings together diverse subject matter expertise across estate planning, wealth management, and scaling SaaS startups. We’re distributed across the U.S., with a mix of fully remote and hybrid roles, and we embrace flexibility while staying closely connected. At Vanilla, you’ll join curious builders and problem-solvers who thrive on speed, autonomy, and impact. Here, you won’t just join a company, you’ll help create it. If you’re excited to tackle hard problems, move quickly, and see your work shape both an industry and a growing startup, we’d love to meet you.

Working Location

This role is a remote position, you must be based out of one of the following states: California, Colorado, Connecticut, Florida, Georgia, Idaho, Illinois, Kentucky, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Rhode Island, South Carolina, South Dakota, Texas, Utah, Virginia, Washington, or Washington, D.C.

Job Summary

As a Pooled Customer Success Manager (CSM) at Vanilla, you’ll be part of a shared Customer Success team supporting a large portfolio of lower-ACV or smaller-license clients. You’ll manage customer outcomes across multiple accounts rather than owning a dedicated book of business.

Reporting to the Senior Director of Customer Success, you’ll focus on efficient onboarding, scalable adoption, proactive retention, and operational excellence. This role is well-suited for a Customer Success professional who excels in structured, team-based environments and enjoys influencing customer retention, adoption, and overall satisfaction at scale.

Responsibilities:

• Manage a shared portfolio of customers, focusing on engagement, adoption, and retention through standardized playbooks.

• Execute automated and trigger-based success plays — including onboarding workflows, adoption nudges, and renewal reminders.

• Monitor account health scores and usage data to identify at-risk customers and drive proactive outreach.

• Support the renewal motion by managing assigned renewal pods or time-based cohorts, ensuring timely communication and coordination with Sales.

• Collaborate cross-functionally with Support, Product, and Marketing to improve the customer experience and surface product insights.

• Contribute to the development and improvement of CS processes, templates, and automation tools for scalable success delivery.

• Document customer interactions and health indicators in CRM systems to maintain full visibility and accountability within the team.

• Track and report portfolio metrics (health, retention, engagement) to drive continuous improvement.

• Act as the voice of the customer, advocating for needs and sharing patterns with leadership to inform strategy.

Required Qualifications:

• 2+ years of experience in Customer Success, Account Management, or related B2B SaaS roles.

• Proven track record of driving customer retention, renewals, and account growth through consultative engagement.

• Demonstrated ability to manage a high volume of customer accounts with strong attention to detail and prioritization.

• Solid understanding of customer retention principles and how to influence renewal outcomes at scale.

• Strong understanding of the customer lifecycle with demonstrated ability to meet or exceed revenue targets.

• Proficiency with CRM and customer success tools (e.g., Salesforce, Totango, Gainsight, or equivalent).

• Analytical and problem-solving skills: able to use data to measure customer health, identify risks/opportunities, and resolve escalations effectively.

• Cross-functional collaboration experience: skilled at being the voice of the customer and influencing product, sales, and support initiatives.

• Process improvement mindset with experience optimizing tools and workflows for scalability.

• Excellent communication and relationship-building skills with high emotional intelligence and empathy.

• Adaptability and tech-savviness: comfortable learning new tools quickly and thriving in a fast-paced, high-growth environment.

Preferred Qualifications:

• Experience in financial services or wealth management,