Senior Director of Product Management - AI-Powered Solutions

About the Role

We’re hiring a Senior Director of Product Management to join our innovative team at Vanilla. This Senior Director of Product Management remote position is pivotal in defining and driving the strategy, execution, and evolution of our AI-powered estate advisory platform. You will be at the intersection of AI innovation and product strategy, shaping how AI transforms advisor workflows while ensuring our products are trusted, accurate, and deeply embedded in how customers operate.

What You'll Do

• Define and evolve Vanilla’s product vision aligned with company goals.
• Establish AI as a core platform capability, focused on delivering 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.
• Drive roadmap execution in close partnership with Engineering.
• Navigate ambiguity, especially in AI tradeoffs (latency, accuracy, model behavior).
• Ship quickly and iteratively, measuring, learning, and improving.
• Build scalable, high-quality products with strong development practices.

Requirements

• 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.
• Comfortable operating in fast-paced, ambiguous environments.
• Experience with AI/ML products (LLMs, prompting, evaluation).
• Strong grasp of AI tradeoffs (accuracy, latency, retrieval, hallucination).
• Ability to turn ambiguity into structured, iterative plans.
• Strong data instincts—defines metrics, runs experiments, evaluates outcomes.

Nice to Have

• Data science background and experience is a plus.

What We Offer

• 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.
• Budget for learning & development and home office setup.
• Paid parking or transit for hybrid and in-office employees.