Senior Director, Product Management

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

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.

Job Summary

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.

What You’ll Do

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

Experience

• 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.

  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.