Remote Director, Customer Success

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.

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 CCO you will lead and scale a high-performing team of Customer Success Managers across both our Pooled and Named segments, and work cross-functionally to ensure a seamless customer journey.

You are a natural builder and collaborator, highly experienced in all things customer success, and 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 not afraid to get into the details and are willing to dive into operational processes, build out workflows, design experiences, and uncover data trends yourself. Your goal is to drive customer retention, expansion, and advocacy by delivering a best-in-class customer experience.

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

Responsibilities

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

• Hire, mentor, and scale a team of Customer Success Managers across Pooled and Named segments, ensuring each receives the appropriate level of engagement and strategic support.

• Design and implement scalable operational frameworks and SOPs tailored to both segments, continuously identifying gaps and bottlenecks in the customer journey.

• Develop and execute strategies to grow retention, reduce churn through proactive at-risk identification and early intervention, and capitalize on upsell and cross-sell opportunities.

• Partner with the customer onboarding team to ensure customers quickly realize value and maintain high engagement throughout their lifecycle.

• Act as a key voice in shaping the company's overall customer success strategy and providing thought leadership to enhance Customer Success at scale.

• Define, track, and report key Customer Success metrics including NPS, churn, customer health scores, and time to value to the executive leadership team.

• Collaborate closely with Product, Sales, and Marketing to align on customer needs, integrate feedback into product development, and ensure a cohesive experience from pre-sales through adoption and beyond.

Qualifications

• 8+ years in Customer Success, Account Management, or similar SaaS roles, including 5+ years building and scaling high-performing CS teams at high-growth startups across both Pooled and Named segments.

• Strong command of CS metrics including NPS, churn, LTV, and customer health, with a data-driven approach to analyzing customer data and delivering measurable improvements.

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

• Hands-on experience with Customer Success platforms such as Totango or ChurnZero and CRM tools such as Salesforce.

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

• 3+ years in financial services or wealth management preferred, with a strong understanding of industry-specific client needs.

The salary range for this role is $160,000 to $185,000. Our compensation packages also include a performance based bonus and equity. Compensation is based on a number of factors and may vary depending on job-related knowledge, skills, and experience.

Benefits:

• Flexible paid time off policy and 10 company-wide paid holidays 

• Parental leave, 6 weeks for all full-time employees and up to 14 weeks for birthing parents

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

• 401K eligibility after one month of employment

• Free estate planning documents

• Budget for learning & development 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.