Principal Product Manager, Agentic AI

Legion

4h • $280,000 - $300,000 • Remote

About The Position

Legion is building AI agents that carry out workforce management work, not agents that describe it. Much of what is presented as AI in workforce management today is a conversational layer over an existing scheduling screen. The more substantial problem — software that reasons over demand, labor regulation, and employee preferences, then acts, with a person in the loop wherever the stakes require one — remains unsolved across the category. Legion intends to solve it, and this role leads the product work to get there. You will take an agent surface from operational research through specification, prototype, evaluation, and enterprise deployment, working hands-on throughout. You will work closely with Legion's AI Lab engineers and with our CEO, who is engaged in this work daily.

Requirements

• 7+ years in product management (Senior) or 10+ years (Principal), including at least 2 years shipping LLM-backed features to external, paying users — not internal tools, proofs of concept, or hackathon projects
• Demonstrated hands-on capability of the kind described above. Expect to show your work.
• Substantial enterprise B2B SaaS experience: multi-tenant architecture, role-based access control, audit trails, single sign-on, data residency, security review, and enterprise procurement. You should be able to anticipate what a customer's security questionnaire will ask about an LLM feature.
• A record of taking an ambiguous, operationally complex domain problem through to a shipped product with demonstrated adoption — not only launch
• Evidence of staying with a product through implementation and owning its quality at release. We will ask about a release you delayed or stopped, what you found, and how you found it.
• The judgment to recognize what current models cannot do reliably, and the willingness to say so when a room expects a different answer
• Comfort working inside a codebase. An engineering background is not required, but you should be able to read the code behind what you are specifying, run it locally, and open a pull request.
• Strong written communication. Legion runs on documents, and candidates are evaluated substantially on how they write.

Nice To Haves

• Direct experience in workforce management, HCM, ERP, supply chain, or another operationally complex enterprise domain with compliance exposure
• Familiarity with labor compliance regimes — predictive scheduling ordinances, meal and rest break rules, union work rules — or demonstrated ability to become fluent in a comparable regulatory domain quickly
• Background in demand forecasting, optimization, or decision systems
• Experience building platform or authoring surfaces that customers configure themselves
• An engineering or technical degree, or prior experience as an engineer or data scientist
• Experience with products sold into frontline-heavy industries: retail, hospitality, healthcare, or manufacturing

Responsibilities

• Agent definition. Determine what an agent is responsible for, which tools it may call, what it must escalate, what it must never do, and what a manager sees when it acts. These decisions affect employee pay and legal compliance. Much of this work is pre-launch, so you will shape the direction rather than inherit it.
• Problem selection. The hardest judgment in agentic product work is identifying which workflows suit an agent and which do not. You will spend substantial time inside customer operations — district managers, store managers, labor operations, frontline employees — and return with a ranked, defensible view of where an agent creates measurable value and where it does not.
• The human-in-the-loop contract. Scheduling decisions affect income, childcare arrangements, and legal protections. For each agent action you will define where autonomy is appropriate, the escalation thresholds, how a manager overrides the system, what is logged, and how a compliance team audits the outcome. Legion treats this as a first-class design problem.
• Build quality. You are accountable for what ships, not for what was specified. That means staying engaged through implementation: reviewing the build against the specification as it comes together, using the product yourself before anyone else is asked to, joining bug triage and design review, catching drift from intent while it is still cheap to correct, and holding a release when the quality is not there. Our customers experience the build, not the document. A well-written specification that produced a product managers do not trust is failed product work, and we assess it that way.
• Evaluation. Build and maintain the evaluation sets that determine whether an agent is ready to ship and whether it is degrading in production — writing the cases, reviewing failure traces, setting the pass criteria. You will be the person who holds a release when the demonstration is persuasive and the evaluation is not.
• Specifications. Legion uses Functional Requirements Documents as its ground-truth specification layer; release notes, enablement material, and sales content are generated from maintained specifications rather than reconstructed from code or institutional memory. Write FRDs that meet that standard and keep them accurate after release. A specification is where the work begins, not where your responsibility ends.
• Commercialization. Partner with go-to-market on packaging, metering, pricing inputs, and field readiness. Agentic products raise difficult commercial questions — what unit to meter, what a customer is paying for when software performs work a person previously did — and you will be expected to hold a considered position on them.
• Design-partner delivery. Lead agent deployments with large enterprise design partners: scoping the pilot, establishing success criteria before it begins, joining failure reviews, and determining what becomes generally available and what remains bespoke.

Benefits

• $0 monthly premium and other flexible medical, dental, and vision plans effective on the first day of employment
• 401k plan
• Discretionary Paid Time Off and Paid Holidays
• Parental Leave
• Equity
• Monthly Wellness Reimbursement
• Monthly Lunch on Legion

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed