Senior Customer Success Onboarding

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: Arizona, California, Colorado, Connecticut, Florida, Georgia, Idaho, Illinois, Kentucky, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah, or Washington

The Senior Customer Success Onboarding plays a critical role in ensuring that new Vanilla customers quickly experience value from our platform. This team member supports the Premium Onboarding Program—focused on high-touch, higher ARR, often many license customers—by facilitating customized project management and a high-quality onboarding and training experience and providing proactive engagement to help customers reach early adoption milestones and value.

You’ll join Vanilla’s Customer Onboarding Team and collaborate closely with AEs and CSMs, leading and delivering guided training, managing customer communications, and ensuring customers in onboarding progress through defined workflows. The goal: drive fast time to value and early ROI before the two-month onboarding mark.

Key Responsibilities

Training & Enablement

• Host Kickoff calls, customized training sessions to the customer and 1:1 screen-sharing sessions to walk customers through setup, features, and best practices.

• Run dedicated customer office hours for large user groups to support users needing extra help during onboarding.

• Maintain and update training materials (videos, guides, decks, and user documentation) to ensure consistency and accuracy across all content.

• Contribute to knowledge base updates—ensuring articles, FAQs, and help content stay up to date after product releases

• Facilitate any technical setup needs (e.g. SSO, IP whitelisting, etc.)

Customer Communication

• Send post-training follow-ups, collect customer feedback, and confirm next steps.

• Identify customers showing signs of low engagement and flag them for follow-up or additional outreach.

• Log and escalate customer questions or technical issues to Vanilla’s Customer Care (i.e. technical support) or Product/Engineering teams as appropriate.

Process & System Support

• Track onboarding progress in Vanilla’s project software/tools, ensuring all milestones and tasks stay on schedule.

• Collaborate/communicate cross-functionally with AE, CSM, Customer Care, Product/Engineering, etc. to keep projects running smoothly and keep all internal stakeholders informed

• Pull, clean, and summarize onboarding metrics, including training attendance, product usage, and time-to-value indicators.

• Support user provisioning and setup tasks to speed up customer activation and improve onboarding efficiency

• Log customer issues and bugs for follow-up with R&D in appropriate tool (e.g., Jira)

  
  

What You’ll Bring

• 5+ years of experience in customer onboarding/training, customer success, or customer support, ideally in a SaaS or service-oriented environment.

• Strong verbal and written communication skills with a friendly, clear, and professional tone.

• Comfort with video conferencing and screen-sharing tools to guide customers.

• Excellent attention to detail and ability to follow structured processes.

• Familiarity with project tracking tools (e.g., GUIDEcx, Totango, Salesforce, etc) is a plus.

• Passion for helping customers succeed and curiosity to learn about the Vanilla platform.

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