Fractional Senior Product Manager AI

We are seeking a seasoned Fractional Senior Product Manager, AI (Freelance) to own and evolve the “intelligence layer” of the platforms experience. This isn’t a prompt‑writing or experimental lab role—our AI must reliably execute real work for our customers: orchestrating actions, automating workflows, and turning unstructured intent into concrete outcomes.

In this role, you will define and ship AI‑powered capabilities that go far beyond chat. You’ll partner closely with design, engineering, and data science to shape how customers interact with the platforms AI, how it chooses the right “skills” to apply, and how we ensure the system is accurate, trustworthy, and grounded in the right data. We’re looking for someone who has built production AI features before and can contribute from day one in a fast‑moving environment.

Role Type: Freelance (Fractional Senior Product Manager, AI)

Location: Remote (US‑based only)

Anticipated

Start Date:

03/23/26

Duration: ~6 months

Anticipated End Date: 09/04/26

Schedule: Monday–Friday, 40 hours per week (no overtime)

Equipment: Personal laptop required

You’ll own the end‑to‑end chat and interaction experience for the platforms AI—how users express intent, how the system responds, and how conversations turn into concrete actions in the product. You will:

• Define and refine conversational flows that feel natural, guided, and outcome‑focused—not just generative or “chatty.”
• Collaborate with design and research to validate user mental models for working with AI in complex project and work management contexts.
• Establish patterns for disambiguation, follow‑ups, confirmations, and error handling that keep users in control and confident.

You will define what our AI is actually capable of doing and how it chooses the right capability at the right time. You will:

• Map, prioritize, and maintain a catalog of AI “skills” (e.g., risk analysis, plan summarization, dependency detection, resource allocation guidance).
• Work with engineering to define orchestration logic: how the system interprets intent, selects tools, sequences actions, and resolves conflicts.
• Define guardrails and eligibility criteria for when certain skills can or should be invoked based on data availability, permissions, and context.

You will own the bar for quality and correctness across AI‑powered experiences in your scope. You will:

• Define the “definition of done” for AI features, including accuracy, grounding, latency, and usability criteria.
• Partner with data science and engineering to create evaluation frameworks, test sets, and QA processes for LLM performance.
• Design feedback loops so customers can correct, rate, or refine AI responses, and so those signals inform continuous improvement.
• Ensure AI is pulling from the correct sources (e.g., specific sheets, projects, work spaces) and respects permissions and data boundaries.

You’ll be the accountable product owner for shipping AI capabilities in a 6‑month horizon. You will:

• Translate strategy and vision into clear product requirements, user stories, and prioritized backlogs.
• Make real‑time trade‑off decisions balancing quality, scope, performance, and timeline.
• Unblock engineering and design by providing crisp decisions, clarifications, and acceptance criteria.
• Partner with GTM, marketing, and customer‑facing teams to define launch plans, messaging, and success metrics.

While this is a hands‑on execution role, you’ll also help sharpen our AI direction. You will:

• Clarify how AI augments core workflows and where it should (and should not) play a central role.
• Define and track success metrics (e.g., task completion, user adoption, satisfaction, reduction in manual work).
• Communicate roadmap, milestones, and risks to leadership and cross‑functional partners in a concise, data‑backed way.

• Deep Product
  
  Experience:
  
  10+ years of product management experience, primarily in enterprise SaaS or other complex B2B software.
• Hands‑on AI Product Background: Direct experience building and shipping products powered by large language models…