Principal Product Manager, Agentic AI

Job Overview:

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.

Responsibilities and Duties:

• 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.
• Problem selection. Identify which workflows suit an agent and which do not, based on substantial time inside customer operations.
• The human-in-the-loop contract. For each agent action, define where autonomy is appropriate, escalation thresholds, manager override, logging, and compliance audit.
• Build quality. Stay engaged through implementation, review the build against the specification, use the product before others, join bug triage and design review, and hold a release when quality is not there.
• Evaluation. Build and maintain evaluation sets that determine whether an agent is ready to ship and whether it is degrading in production.
• Specifications. Write Functional Requirements Documents that serve as the ground-truth specification layer and keep them accurate after release.
• Commercialization. Partner with go-to-market on packaging, metering, pricing inputs, and field readiness.
• Design-partner delivery. Lead agent deployments with large enterprise design partners, including pilot scoping, success criteria, failure reviews, and generally available versus bespoke decisions.

Technical Expectations:

Legion is looking for a product manager who builds, rather than one who directs others who build. In a typical week, this role involves:

• Writing and iterating on prompts and system prompts directly, and explaining why a change improved a behavior
• Standing up a working prototype of a proposed agent, including tool definitions, structured outputs, retries, and guardrails
• Using agentic coding tools (Claude Code or equivalent) daily
• Reviewing an execution trace and diagnosing whether a failure originates in a tool description, a retrieval gap, a context-window constraint, an under-specified output schema, or a model limitation
• Building and running evaluation sets, and interpreting the results
• Holding an informed position on retrieval design, tool-use patterns, structured output, model routing, latency and cost trade-offs, and multi-tenant safety
• Opening pull requests against the codebase. This is permitted and encouraged, but not required.
• Following model releases, agent frameworks, and protocol changes, and translating them into roadmap implications within days rather than quarters

Required Skills and Qualifications:

• 7+ years in product management (Senior) or 10+ years (Principal), including at least 2 years shipping LLM-backed features to external, paying users
• Demonstrated hands-on capability, with work shown to the company
• Substantial enterprise B2B SaaS experience, including multi-tenant architecture, role-based access control, audit trails, single sign-on, data residency, security review, and enterprise procurement
• A record of taking an ambiguous, operationally complex domain problem through to a shipped product with demonstrated adoption
• Evidence of staying with a product through implementation and owning its quality at release
• The judgment to recognize what current models cannot do reliably
• Comfort working inside a codebase, with the ability to read code, run it locally, and open a pull request
• Strong written communication

Preferred Qualifications and Attributes:

• Direct experience in workforce management, HCM, ERP, supply chain, or another operationally complex enterprise domain with compliance exposure
• Familiarity with labor compliance regimes such as predictive scheduling ordinances, meal and rest break rules, and union work rules
• 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 such as retail, hospitality, healthcare, or manufacturing

Scope of Role:

• This is an individual contributor role with no management responsibility at present.
• The role is accountable for what ships, not only for what is specified.
• This is not an AI strategy or vendor-evaluation role.
• The role requires forming an independent point of view from operational research.
• The environment carries genuine ambiguity, and model capabilities shift underneath the roadmap.

Selection Process:

The process includes a practical exercise in which candidates produce an agent design and a working prototype they built themselves, using any model provider they prefer. The exercise is then discussed with the people the candidate would work alongside. Candidates are compensated for their time.

Compensation and Benefits:

Salary Range: $280,000.00-$300,000.00 + Bonus + Stock Equity

As a fully remote employer, pay is determined using local, national, and industry-specific survey data. The posted range is based on national data and may be refined for a candidate's region, town, or cost of living.

Benefits include, but are not limited to:

• $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

About Legion:

Join Legion's mission to turn hourly jobs into good jobs. Legion is a remote, mission-driven team. The Legion WFM platform is AI-driven and is designed to maximize labor efficiency and employee engagement simultaneously.

Equal Employment Opportunity:

Legion Technologies is an equal-opportunity employer and is committed to maintaining a diverse and inclusive work environment. All qualified applicants will be considered for employment without regard to legally protected status.

Disability Accommodation:

For individuals with disabilities who need additional assistance at any point in the application and interview process, please email [email protected].