Director of Customer Success

About Us

Estate planning is vital for anyone who wants to ensure their loved ones are cared for when they’re gone. But traditional estate planning is broken. It’s confusing, expensive, and tedious, and it’s often done without regard to a person’s financial plan. Vanilla is here to change all that. We are reinventing estate planning for financial advisors, attorneys, and their clients. We’re transforming it into an ongoing conversation, where dense legal documents are brought to life through easy-to-understand visualizations, and considered  in concert with clients’ financial plans and evolving life milestones and goals.

Vanilla is the world’s first estate advisory platform, built by advisors and estate professionals to help deliver a modern, visual estate planning experience to their clients. Harnessing a purpose-built AI engine called VAI, the Vanilla platform provides valuable insights to advisors and attorneys while demystifying the planning process for clients at all levels of wealth. Vanilla supports the entire estate planning process, including understanding client goals and current plans, visualizing the plan, and strategizing on taxes. Clients can even create trusts, healthcare directives, powers of attorney, and more through Vanilla. The Vanilla platform enables advisors, planners, and attorneys to foster stronger relationships, achieve greater retention, and help their clients build meaningful legacies.

Job Summary

As the Director of Customer Success, you will be responsible for driving the long-term success and satisfaction of our customers. Reporting to the SVP of Customer Experience, you will lead and scale a high-performing team of Customer Success Managers (CSMs) and work cross-functionally to ensure a seamless customer journey. You are highly experienced in all things customer success and are ready to build stronger operations to help your team scale to meet the growing needs of a fast-paced and maturing customer base. You are a natural builder and collaborator - going above and beyond to work across teams to solve customer needs. Your goal is to drive customer retention, expansion, and advocacy by delivering a best-in-class customer experience.

This role is a remote position, you must be based out of one of the following states: CA, CO, CT, DE, FL, GA, ID, IL, IN, KY, MA, MD, ME, MN, NC, NH, NJ, NY, OH, OK, PA, RI, SC, SD, TX, UT, VA, WA, or WA D.C.

Responsibilities 

• Build strong, trust-based relationships with key customer stakeholders to drive loyalty and advocacy, translating successful partnerships into case studies and testimonials.

• Builder stronger operational infrastructure and standard operating procedures that help scale and focus the role of customer success for each customer segment. 

• Develop strategies to increase customer retention and identify upsell/cross-sell opportunities to grow existing customer relationships.

• Oversee the customer onboarding process to ensure customers quickly realize the value of our product, while maintaining a high level of customer engagement throughout their lifecycle.

• Develop proactive strategies to identify at-risk customers and implement early intervention tactics to reduce churn.

• Hire, mentor, and manage a growing team of Customer Success Managers, ensuring they have the tools and resources to deliver exceptional service and meet key performance goals.

• Define and track key Customer Success metrics (e.g., NPS, churn, customer health scores, time to value). Present actionable insights and recommendations to the SVP and leadership team.

• Continuously improve Customer Success processes and workflows, identifying bottlenecks or gaps in the customer journey that could impact customer satisfaction.

• Work closely with Product, Sales, and Marketing teams to ensure customer feedback is integrated into product development and to align on customer needs and expectations.

• Partner with the Sales, Product, and Support teams to ensure a cohesive customer experience from pre-sales through product adoption and ongoing support.

• Act as a key voice in shaping the company’s overall customer experience strategy, providing thought leadership on how to enhance customer success at scale.

Qualifications

• 10+ years of experience in Customer Success, Account Management, or similar roles in a SaaS or technology company.

• 3+ years of experience managing a team. 

• Proven track record of building and leading high-performing Customer Success teams at a fast-growing startup or tech company.

• Strong understanding of customer success metrics (e.g., NPS, churn, LTV, customer health) and how to drive improvements.

• Experience working with C-level executives and managing relationships with large, complex enterprise customers.

• Ability to mentor and coach a team, fostering a collaborative and customer-centric culture.

• Data-driven approach to decision-making, with the ability to analyze customer data and present insights clearly.

• Experience with Customer Success software (e.g., Gainsight, ChurnZero) and CRM platforms (e.g., Salesforce) is preferred.

Benefits

• Flexible paid time off policy and 12 company-wide paid holidays 

• Parental leave, 4 weeks for all full-time employees and up to 12 weeks for birthing parents

• Medical, dental, and vision benefits coverage for employees and their families 

• 401K and employer match eligibility after one month of employment

• Budget for learning & development, health & wellness, and home office setup 

• Paid parking or transit for hybrid and in office employees

Vanilla Technologies Inc. (dba "Vanilla") provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.

Vanilla participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S.