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AscertainAscertainUnited States

Staff Product Manager, Automation

Staff Product Manager owning the roadmap for an AI automation platform that handles healthcare administrative workflows. Requires 8+ years PM experience with technical/platform products, fluency in LLMs/agents, and strong analytical skills to translate complex ops into agent specs and define evals/observability.

160k – 220k
Remote8+ YOEProduct Management

About the role

Responsibilities

  • Own the roadmap for our automation vertical, from problem definition and opportunity sizing through agent design, rollout, and measurable outcomes in production.
  • Partner with operations and engineering to translate messy real-world workflows into agent-executable specs. Shadow ops teams, reverse-engineer payer portals, read denial letters, and turn all of it into structured requirements an agent can act on.
  • Define the evaluation and observability story for your agents. Manage the metrics, evals, guardrails, and human-in-the-loop escalation paths.
  • Prioritize ruthlessly across competing customer asks, platform investments, and net-new automation surfaces. Decide what becomes productized vs. what stays bespoke.
  • Partner with GTM on positioning, pricing signals, and customer expansion - automation ROI is the story, and you'll help tell it with the data to back it up.

Requirements

  • 8+ years of product management experience, with meaningful time spent on technical, platform, or workflow-automation products.
  • Demonstrated track record of shipping products that involve integrating with messy, legacy, or enterprise systems (EHRs, payer systems, ERPs, imaging systems, or similar).
  • Fluency with modern AI/ML systems (LLMs, agents, RAG, evals, tool use); able to credibly scope what an agent can and can't do.
  • Strong analytical skills; comfortable in SQL, notebooks, or similar to answer product questions independently.
  • Experience working in zero-to-one or early-scaling environments.
  • Excellent written communication skills.

Nice-to-Haves

  • Healthcare experience.
  • Builder mindset (ex-engineer or hobbyist who has shipped tools).
  • Ex-founder or early-stage employee experience.
  • Genuine belief that healthcare administration is worth fixing.

Compensation & Benefits

  • Competitive salary and meaningful equity.
  • Comprehensive health benefits.
  • Flexible remote-friendly work model (hybrid for NYC-based team members).
  • Opportunity for ownership and growth at an early-stage company.

Skills

Product ManagementLLMsAI AgentsRAGEvalsSQLWorkflow AutomationEhr IntegrationPayer SystemsEnterprise Systems Integration

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