Senior Director, Product Management

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.

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, Rhode Island, South Carolina, South Dakota, Texas, Utah, Virginia, Washington, or Washington, D.C.

We’re looking for a Sr. Director, Product Management to define and drive the strategy, execution, and evolution of Vanilla’s product platform.

This role sits at the intersection of AI innovation, product strategy, and hands-on execution. You’ll shape how AI transforms advisor workflows while ensuring our products are trusted, accurate, and deeply embedded in how customers operate.

You’ll lead a small, high-impact team of Product Manager and UX Designers while operating as a player-coach - setting direction, collaborating on strategy, driving alignment, and staying close to the work. This role reports into the CTO and is critical in evolving our platform and position, product-market fit, scaling, and building durable competitive advantage through AI.

Define Product & AI Strategy

• Own and evolve Vanilla’s product vision aligned with company goals

• Establish AI as a core platform capability, focused on real customer value

• Balance innovation with trust - ensuring accuracy, transparency, and reliability

• Translate strategy into a clear, prioritized roadmap across near- and long-term horizons

Lead Execution & Delivery

• Drive roadmap execution in close partnership with Engineering

• Navigate ambiguity, especially in AI tradeoffs (latency, accuracy, model behavior)

• Ship quickly and iteratively - measure, learn, and improve

• Build scalable, high-quality products with strong development practices

Build Customer & Domain Insight

• Develop deep expertise in advisor workflows and high-trust financial decisions

• Lead discovery through research, interviews, and rapid validation

• Ground decisions in user needs, market context, and product data

• Champion a trust-first approach to correctness, transparency, and security

Drive Go-to-Market & Growth

• Partner with Marketing, Sales, and CX on positioning and launches

• Align product, pricing, and packaging with revenue goals

• Drive adoption through continuous product and GTM iteration

Build & Lead a High-Performing Team

• Hire and develop exceptional PMs and Designers

• Set a high bar for product thinking, execution, and AI fluency

• Ensure the team has the necessary resources and support to consistently meet high performance expectations.

• Foster a culture of ownership, speed, and continuous improvement

• Implement lightweight processes that enable autonomy and accountability

Own Product Performance

• Define and track key product and business metrics

• Use data to inform prioritization and decision-making

• Communicate progress and outcomes to leadership and stakeholders

Drive Cross-Functional Alignment

• Align Engineering, GTM, and leadership on priorities and outcomes

• Clearly communicate strategy, progress, and insights

• Influence decisions through strong judgment, data, and customer con

• 10+ years in product management, including team leadership

• Demonstrable track record building and scaling B2B SaaS products

• Experience in fintech, wealth management, or other high-trust domains preferred but not required

• Comfortable operating in fast-paced, ambiguous environments

AI & Technical Fluency

• Experience with AI/ML products (LLMs, prompting, evaluation)

• Strong grasp of AI tradeoffs (accuracy, latency, retrieval, hallucination)

• Effective partner to Engineering and Data teams in shipping AI features

• Actively uses and promotes AI tools in day-to-day work

• Demonstrable experience with agentic coding, design, and testing

Product & Analytical Skills

• Ability to turn ambiguity into structured, iterative plans

• Strong data instincts—defines metrics, runs experiments, evaluates outcomes

• Experience building products where trust, accuracy, and reliability are critical

• Data science background and experience is a plus

Leadership & Mindset

• Customer-obsessed, with appreciation for high-stakes financial decisions

• High ownership and accountability for outcomes

• Bias for action—prioritizes speed, learning, and iteration

• Clear communicator across technical and business audiences

• Pragmatic and curious, grounded in delivering real customer value

The salary range for this role is $230,000 to $265,000. 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.