Senior 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 Senior 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, and WA D.C.

Responsibilities

• Build strategic, trust-based relationships with key customer stakeholders to drive loyalty, advocacy, and long-term partnerships.

• Design and implement scalable operational frameworks and standard operating procedures tailored to diverse customer segments.

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

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

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

• Hire, mentor, and lead a growing team of Customer Success Managers, providing the tools and resources necessary to achieve exceptional outcomes.

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

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

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

• Partner with 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 and providing thought leadership to enhance Customer Success at scale.

Qualifications

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

• 5+ years of experience managing and scaling high-performing teams, including leadership of senior managers.

• Proven track record of building and leading Customer Success organizations at high-growth startups or technology companies.

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

• Demonstrated ability to manage relationships with enterprise-level customers and C-suite executives.

• Experience mentoring and coaching teams, fostering a collaborative and customer-centric culture.

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

• Hands-on experience with Customer Success software (e.g., Gainsight, ChurnZero) and CRM platforms (e.g., Salesforce).

• Exceptional communication, presentation, and stakeholder management skills, with a proven ability to influence cross-functional teams.

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.