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Holistiplan is a B2B SaaS platform serving financial advisors with award-winning software for tax planning, insurance, and estate planning. The company is expanding its use of AI, particularly through Document Intelligence—a capability that automatically extracts and interprets data from tax returns and client documents.
You'll join as Product Manager for AI & Document Intelligence, reporting directly to the CEO in a high-visibility, high-ownership role. Your mandate is to shape how AI shows up across the entire Holistiplan product suite, not just within one feature area. You'll serve as the company's standard-setter for responsible, effective AI product development.
Key responsibilities include:
• Partner with the CEO to define and communicate AI vision and strategy across the company, translating that vision into a concrete, sequenced roadmap.
• Own the Document Intelligence product line—drive improvements in extraction accuracy, reduce cost-per-document, and expand the range of document types and data points the system can reliably handle.
• Identify, scope, and ship new AI-powered features and products from early concept through launch, working closely with engineering and design teams.
• Define and operate evaluation frameworks for model behavior and output quality; establish prompt design patterns and AI standards that other product teams can adopt.
• Make clear-eyed tradeoff decisions between accuracy, latency, and cost across model and architecture choices; advise when AI should (and shouldn't) be used.
• Stay current on the model and tooling landscape; serve as the internal expert advising other product teams on responsible AI integration.
• Establish and track key metrics—AI adoption, extraction accuracy, cost-per-document—to guide prioritization and measure success.
• Talk directly to financial advisors and internal teams to identify where AI is underperforming or leaving value on the table; turn insights into a prioritized backlog.
You'll need hands-on experience shipping AI/ML-powered features (LLMs, extraction models, NLP systems). You should have working fluency with evals, prompt design, model behavior, and the accuracy/latency/cost tradeoffs involved in model selection and tuning. A track record of taking products from ambiguous concept to shipped feature is essential, as is strong product judgment to distinguish genuinely valuable AI use cases from novelties.
You'll operate with high visibility and autonomy, working directly with executive leadership on strategy. Excellent communication skills—translating technical AI concepts for non-technical stakeholders and vice versa—are critical. Strong analytical instincts and comfort defining and tracking quality/performance metrics round out the profile.
Nice-to-have experience includes document extraction, OCR, structured data extraction from unstructured documents, fintech/tax/insurance/financial planning software backgrounds, familiarity with LLM evaluation frameworks, experience establishing AI standards across teams, and startup experience.
