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

It is preferred that this person work hybrid from our Bellevue, WA headquarters. (For the right candidate, we will consider a remote US position.)

If remote, 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 an Enterprise Customer Success Manager (Enterprise CSM) at Vanilla, you will serve as the strategic relationship anchor for some of our largest and most complex customers. You will partner closely with Account Executives, leadership, and product experts to guide enterprise accounts from pilot to contract to long-term growth.

Your mission is to help customers maximize adoption of Vanilla’s platform, uncover new opportunities for expansion, and ensure successful program execution across their organizations. This role blends customer advocacy, project/program management, influencing, product expertise, and strategic relationship building. You will work directly with executives, advisors, and end users to drive adoption and measurable impact, positioning Vanilla as a long-term partner in their success.

Responsibilities

• Anchor enterprise relationships by serving as the primary strategic contact for large accounts, building trusted advisor relationships with executives and stakeholders.

• Drive adoption and outcomes by guiding customers from pilot through enterprise rollout, ensuring alignment with customer goals and success metrics.

• Co-own enterprise account plans with Account Executives, aligning on adoption, retention, and expansion revenue goals.

• Identify expansion opportunities by proactively uncovering new use cases, business units, or advisor teams where Vanilla can deliver additional value.

• Lead program & project management of enterprise accounts, ensuring timely execution of onboarding, enablement, and adoption plans that drive measurable ROI.

• Collaborate with Account Executives to develop and execute enterprise account plans that align to revenue, adoption, and retention goals.

• Deliver product expertise and strategic guidance to help customers maximize value, solve complex problems, and integrate Vanilla into their workflows.

• Act as the voice of the customer internally by providing feedback to Product, Marketing, and Leadership to influence roadmap and customer experience improvements.

• Monitor account health and risks, mitigating churn by managing escalations and ensuring long-term customer satisfaction.

• Communicate effectively across executive, advisor, and operational levels, tailoring messaging to diverse audiences.

Required Qualifications

• 10+ years of experience in Customer Success, Account Management, or similar customer-facing roles within SaaS, including 3+ years working with Enterprise or strategic accounts.

• Proven ability to manage and grow large, complex customer relationships, including working directly with C-level and senior executives.

• Track record of driving adoption, retention, and expansion within enterprise accounts.

• Strong project and program management skills—able to coordinate stakeholders, manage timelines, and deliver successful outcomes.

• Excellent communication and presentation skills; able to engage both executive and practitioner audiences.

• Deep collaboration skills with cross-functional teams, including Sales, Product, and Support.

• Analytical and strategic thinker with the ability to translate customer data and insights into actionable recommendations.

• High emotional intelligence and relationship-building skills.

• Self-starter who thrives in a fast-paced, high-growth environment.

Preferred Qualifications

• Experience in financial services, wealth management, or estate planning.

• Familiarity with SaaS adoption frameworks, customer health metrics, and enterprise change management practices.

• Experience in working for a technology and/or software company.

• Exposure to value-based selling methodologies or consultative expansion motions.

The salary range for this role is $140,000 to $160,000. 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, 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 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.

Compensation Range: $140K - $160K