Senior Director, Product Management
About The Position
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.
Requirements
- 10+ years in product management, including team leadership
- Demonstrable track record building and scaling B2B SaaS products
- 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
- 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
- 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
Nice To Haves
- Experience in fintech, wealth management, or other high-trust domains preferred but not required
- Data science background and experience is a plus
Responsibilities
- 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
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
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
