Senior Manager, Customer Support

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.

Build the Next Generation of Support at Vanilla

Vanilla is scaling rapidly across customer segments and expanding product capabilities. As our customer base grows in complexity and sophistication, our Support function must evolve from reactive issue resolution to a strategic driver of clarity, retention, and product insight.

We are hiring a Sr Manager of Customer Support to architect the structural foundation for long-term scale. This leader will build a disciplined, data-driven, high-impact Support organization that reduces customer effort, strengthens cross-functional feedback loops, and ensures operational excellence keeps pace with company growth.

This is not a ticket-queue management role. It is a systems-building leadership role focused on designing scalable support models, embedding operational rigor, and positioning Support as a meaningful lever for retention and expansion. You will own and architect the end-to-end Support experience — from service design to tooling strategy to cross-functional alignment.

Within your first year, you will:

• Establish clear, tiered support models aligned to customer complexity and value

• Implement operational rigor across SLAs, escalation pathways, QA, and performance management

• Build structured feedback loops between Support, Product, and Engineering that reduce systemic friction

• Launch a scalable self-service and knowledge strategy that increases deflection and consistency

• Improve measurable Support contribution to retention and expansion

• Ensure Support operations scale predictably alongside company growth

What You’ll Do:

• Strengthen support operations through scalable processes, clear escalation models, quality standards, root cause analysis, and strong accountability mechanisms

• Reduce customer effort by identifying recurring friction patterns and systemic ticket drivers

• Partner with Product and Engineering to resolve high-impact issues and implement structured, data-driven feedback loops with measurable reduction targets

• Build and scale a self-service and knowledge strategy, owning knowledge base architecture, governance, and quality standards

• Design scalable troubleshooting workflows that improve resolution speed and consistency

• Architect segmented support models that align service levels to customer needs and unit economics, ensuring efficient and strategic resource allocation

• Position Support as a key retention lever by partnering with Customer Success to identify risk signals, establish proactive intervention triggers, and improve early-lifecycle experience consistency

• Deploy AI-assisted support capabilities strategically, balancing efficiency gains with customer experience and quality

• Manage outsourcing partners against clearly defined performance and quality standards

• Build a culture of ownership and execution through clear accountability expectations, disciplined operating rhythms, and strong cross-functional coordination

What You Bring

• 6+ years of SaaS Support or Customer Operations leadership experience

• Proven experience building and scaling support functions in high-growth environments

• Strong people leadership skills, with a track record of coaching, developing, and holding high-performing teams to clear standards

• Demonstrated success reducing structural customer effort and addressing systemic friction

• Deep expertise in knowledge management systems and scalable self-service strategy

• Strong cross-functional partnership experience with Product and Engineering

• Experience designing segmented support models aligned to customer needs and business economics

• Familiarity with AI and automation tools within modern Support environments

• Executive presence paired with strong operational rigor and data-driven decision-making

The salary range for this role is $135,000 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.

• 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.