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Principal Product Manager (AI)

Wisdom

This Principal Product Manager role involves leading the strategy and execution for AI-driven dental billing workflows. You will oversee the transition from human-assisted tools to autonomous AI agents.

What you’d own

  • Strategy and roadmap for an AI-first product
  • Agentic workflows and human-in-the-loop UX patterns
  • Gradual autonomy models for AI actions
  • Translation of tribal knowledge into structured product workflows

Who it’s for

A fit if you…

  • ✓You have 8+ years of PM experience with at least 3 years specifically in AI/ML
  • ✓You have shipped products using LLMs and agent frameworks
  • ✓You are comfortable prototyping flows in code and shipping PRs
  • ✓You have experience in regulated industries like healthcare or fintech

Not for you if…

  • ✗You prefer a high-level strategy role without getting into the mechanics of eval infra and prompt regressions
  • ✗You are not comfortable with a 'builder' culture where you may need to prototype in code
  • ✗You prefer working on simple UI wrappers rather than complex agentic logic and escalation paths

Reading between the lines

  • The requirement to shadow veterans and translate 'tribal knowledge' implies the product discovery will be heavily qualitative and rooted in manual, legacy processes.
  • The mention of 'small pods, all builders' suggests a high degree of autonomy and a lack of traditional middle management.
  • The focus on 'eval infra' and 'prompt regressions' signals that the team is dealing with production-level AI challenges, not just experimental features.

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Full job description

About Wisdom

Wisdom blends industry expertise with advanced technology to make dental practices work better for everyone involved. We believe dentistry is about people, and we exist to make the future of dentistry stronger and more sustainable for dentists, their teams, and the patients they serve. We match administrative teams with expert billers and custom-built technology to take on the heavy lifting of dental billing while maximizing dentists’ time in-office, and their bottom line.

Coming from a fresh $21M Series A round of funding we are looking for exceptional candidates to help us build a category-defining company. Wisdom has employees across the US.

The Role: Principal Product Manager (AI)

Dental insurance billing is one of the largest manual workflows in US healthcare. Claims aging, appeals, posting, follow-ups makes for work that today eats entire FTE teams at every dental practice. The expertise that makes it run lives in the heads of veteran dental billers. We're building AI agents that work alongside them and support them through these workflows.

We're hiring a Principal PM to own a major surface of this. Small pods, all builders, reporting to the Head of Product. You'll help shape Wisdom's product strategy for the next 1-3 years.

What You'll Do

  • Own strategy and roadmap for an AI-first product. Balance short-term wins (human-assisted tools) with long-term bets (autonomous AI agents).
  • Shadow revenue specialists, billers, and dental office managers to understand workflows end-to-end. Translate tribal knowledge from 10+ year industry veterans into structured product workflows and context for AI.
  • Be on the forefront of AI design patterns. Help us build new agentic workflows, human-in-the-loop UX patterns, AI-to-human escalation paths, and audit trails.
  • Define gradual autonomy models: when should AI act autonomously vs. escalate to humans.

What We're Looking For

  • 8+ years as a Product Manager, with at least 3 years working on AI/ML products.
  • You're already shipping AI products. You've built things with LLMs and agent frameworks, you've felt the pain of eval infra and prompt regressions, and you have strong opinions on the mechanics of how we build.
  • You leverage AI across the entire stack of the job: drafting and pressure-testing strategy, running synthetic user research, building evals before specs, prototyping flows in code, and shipping PRs when it's faster than writing them up. You treat AI like a co-worker you're constantly delegating to and learning from.
  • You've built pure agentic or human-in-the-loop systems before. You can make tradeoffs between "AI decides, AI performs," "AI suggests, human approves," "AI acts, human audits," or even "AI skipped, human only." Bonus if you've done this in healthcare, fintech, or another regulated space where being wrong has massive consequences.

Wisdom is an equal opportunity employer. We provide employment opportunities without regard to age, race, color, ancestry, national origin, religion, disability, sex, gender identity or expression, sexual orientation, veteran status, or any other protected status in accordance with applicable law.

About Wisdom

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Wisdom is a dental revenue cycle management company that lets dental practices outsource insurance billing and patient collections, handling claim submission and scrubbing, payment posting, aging AR, and insurance verification so offices get paid faster with less paperwork. It pairs experienced human billers with an AI-powered platform built by people who've worked in real practices, aiming to lower AR and recover more revenue for its clients. Founded in 2023 by CEO Stoyan Kenderov (ex-Plastiq, LendingClub, Intuit) and dental-billing veteran Ashley Bond, it raised a $21M Series A (part of $28M total) led by Permanent Capital Ventures. The team is roughly 50 to 200 people and values-driven around customer delight and moving fast.

Healthcare & Health TechFinancial Services & Fintech

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