Senior Product Manager

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.

We’re looking for a Senior Product Manager to lead and evolve VAI, the intelligence layer that powers our AI-driven experiences. This is a uniquely impactful role: you’ll define how advisors interact with AI, how the system handles uncertainty, and how we build trust in an industry where accuracy truly matters. This is a high‑ambiguity environment. You’ll be building new capabilities across our abstraction workflows, document experiences, and AI‑powered inputs.

Success requires balancing user needs, model behavior, legal constraints, and business priorities—often with incomplete information.

• Translate high‑level direction into clear, buildable scopes without waiting for perfect inputs
• Partner with product leadership on priorities, then own the execution end‑to‑end
• Write crisp, detailed requirements and user stories that anticipate edge cases, failure states, and dependencies
• Work closely with engineering to break work down, remove blockers, and keep momentum high
• Define success metrics and build lightweight dashboards or queries to monitor them
• Lead discovery yourself—interviews, workflow mapping, quick validation loops
• Collaborate with design to rapidly prototype, test, and refine interaction patterns
• Identify opportunities for simplification across VAI workflows and contribute to architectural cleanup
• Champion AI internally by using it in your workflow and helping teammates adopt AI‑first processes
• Drive alignment across engineering, design, and GTM so shipped work stays coherent and connected
• Ship quickly, measure, learn, and iterate

• 5+ years in product management, with direct ownership of shipping features
• Experience working with AI or ML‑enabled products, ideally with hands‑on familiarity (prompting, testing models, using AI tools to validate assumptions)
• Comfortable turning messy, ambiguous problem spaces into structured, incremental delivery plans
• Demonstrated ability to work closely with engineering and understand tradeoffs (latency, accuracy, model behavior, retrieval constraints)
• Confident using AI tools in your own workflow (analysis, spec writing, research, QA)
• Strong analytical skills and comfort working directly with data (SQL, Mixpanel, Looker, or similar is a plus)
• Excellent written communication—you can write fast, clearly, and with enough precision for engineers to execute
• Experience at startups, scale‑ups, or any environment where velocity and autonomy matter
• Experience in a SaaS company shipping commercial‑grade software

• Familiarity with LLMs, RAG architectures, or prompt engineering at a working level
• Experience in fintech, wealth tech, or regulated industries
• Background in B2B SaaS serving professional users (advisors, attorneys, accountants)
• You’ve worked on trust and accuracy problems—where getting it wrong matters

• Curious by default. You dig into how things work, especially when they’re new.
• Comfortable with "we don't know yet" as a starting point.
• Direct. You say what you think, ask hard questions, and don't hide behind process.
• Bias toward action. You'd rather ship and learn than wait for perfect information.
• Grounded. You care about users, not…