Location: Remote (US) | Job Type: Full-Time

Who We Are

Holistiplan provides award-winning software built for financial advisors, originally focused on tax planning and now expanding into insurance and estate planning. Our tools — Tax Report, Scenario Analysis, and Explainer reports help advisors quickly make sense of complex client situations. Document Intelligence, which automatically extracts and interprets data from tax returns and other client documents, is the engine that makes much of that possible.

Our vision is for AI to not only drive the backend processes for data extraction purposes, but also to improve how advisors experience Holistiplan. We’re hiring a Product Manager to lead and shape how our product interacts with AI.

The Opportunity

This is a high-visibility, high-ownership role. You’ll work directly with our CEO to shape the vision and direction for AI functionality across Holistiplan — not just within one feature area, but as a standard-setter for how the whole company builds with AI. You’ll own our existing Document Intelligence capabilities while also identifying and building the next generation of AI-powered features and products.

You’ll sit at the intersection of genuine technical depth — evals, prompt design, model behavior — and product judgment about what’s worth building. If you want to help define a company’s AI strategy from a position of real influence where you can impact hundreds of thousands of financial advisors and their clients, this is the role for you.

What You’ll Do

• Partner with our CEO on AI vision and direction. Help set the strategy for how AI shows up across Holistiplan’s products, and translate that vision into a concrete, sequenced roadmap.
• Own Document Intelligence. Drive the roadmap for our existing document extraction and interpretation capabilities — improving accuracy, reducing cost-per-document, and expanding what document types and data points we can reliably handle.
• Bring new AI products to market. Identify, scope, and ship new AI-powered features and products, from early concept through launch, working closely with engineering and design.
• Set the bar for AI quality. Define and run evaluation frameworks for model behavior and output quality; establish prompt design patterns and AI standards that other teams across the company can build on.
• Make the tradeoffs. Balance accuracy, latency, and cost across model and architecture choices, and make clear-eyed calls about where AI should (and shouldn’t) be used.
• Be the internal expert. Stay current on the model and tooling landscape, and advise other product teams on how to responsibly and effectively incorporate AI into their own roadmaps.
• Define success. Establish and track the metrics that matter — AI adoption, extraction accuracy, cost-per-document — and use them to guide prioritization.
• Work close to the ground. Talk to advisors and internal teams to understand where AI is falling short or leaving value on the table, and turn that into a prioritized backlog.

What We’re Looking For

• Experience as a technical product manager, ideally with direct exposure to shipping AI/ML-powered features (LLMs, extraction/NLP models, or similar).
• Working fluency with the mechanics of AI product development — evals, prompt design, model behavior, and the accuracy/latency/cost tradeoffs involved in choosing and tuning models.
• A track record of taking a product from ambiguous concept to shipped feature, including scoping, sequencing, and working directly with engineering.
• Strong product judgment — the ability to distinguish a genuinely valuable AI use case from a novelty, and to say no to the latter.
• Comfort operating with a high degree of visibility and autonomy, including working directly with executive leadership on strategy.
• Excellent written and verbal communication — able to translate technical AI concepts for non-technical stakeholders, and vice versa.
• Strong analytical instincts and comfort defining and tracking quality/performance metrics for a product area.

Nice to Have

• Experience with document extraction, OCR, or structured data extraction from unstructured documents.
• Background in fintech, tax, insurance, or financial planning software.
• Familiarity with evaluation frameworks and tooling for LLM-based products.
• Experience establishing AI usage standards or best practices across multiple teams or product lines.
• Experience working in a fast-growing startup environment with evolving processes.

Benefits

• Be part of a fast-growing company focused on transforming the financial planning industry
• Opportunity to shape an innovative software product that directly impacts the work of financial planners and their clients
• Competitive salary and equity options
• 401(k) matching
• Health insurance (Medical/Dental)
• Flexible working hours and remote work culture
• Unlimited PTO with a team that uses and encourages time off
• Monthly Wellness & Office Space Reimbursements
• Opportunities for professional growth and development
• A collaborative and innovative work environment

To Apply : email your resume to jobs@holistiplan.com.