Principal Product Manager, Agentic AI

Headquarters: Remote, United States Source: weworkremotely

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. These decisions affect employee pay and legal compliance.
Problem selection: Identify 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) to identify where an agent creates measurable value.
The human-in-the-loop contract: 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.
Build quality: You are accountable for what ships. This includes reviewing the build against the specification, using the product yourself, joining bug triage and design review, and holding a release when the quality is not there.
Evaluation: Build and maintain the evaluation sets that determine whether an agent is ready to ship and whether it is degrading in production. You will be the person who holds a release when the evaluation is not persuasive.
Specifications: Write Functional Requirements Documents (FRDs) that serve as the ground-truth specification layer. 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 scoping pilots and establishing success criteria.

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.
Standing up a working prototype of a proposed agent (tool definitions, structured outputs, retries, guardrails) before engineering is asked to build anything.
Using agentic coding tools (Claude Code or equivalent) daily for prototyping, data analysis, and reading the codebase.
Reviewing execution traces to diagnose failures (retrieval gaps, context-window constraints, etc.).
Building and running evaluation sets and interpreting results.
Holding an informed position on retrieval design, tool-use patterns, structured output, model routing, latency/cost trade-offs, and multi-tenant safety.
Opening pull requests against the codebase. Pushing code is permitted and encouraged.
Following model releases and agent frameworks to translate them into roadmap implications within days.

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; expect to show your work.
Substantial enterprise B2B SaaS experience (multi-tenant architecture, RBAC, audit trails, SSO, data residency, security review).
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 (reading code, running it locally, opening pull requests).
Strong written communication.

Preferred Qualifications

Direct experience in workforce management, HCM, ERP, supply chain, or other operationally complex enterprise domains.
Familiarity with labor compliance regimes (predictive scheduling, meal/rest break rules, 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 (retail, hospitality, healthcare, manufacturing).

Scope of Role

This is an individual contributor role.
The role is accountable for what ships, not just 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.

Selection Process

Our process includes a practical exercise: a sanitized workforce management problem for which candidates produce an agent design and a working prototype. We weigh this heavily and compensate candidates for the time.

Compensation & Benefits

Salary Range: $280,000–$300,000 + bonus (tied to business outcomes) + Stock Equity.

Benefits include:

$0 monthly premium and other flexible medical, dental, and vision plans (effective day one).
401k plan.
Discretionary Paid Time Off and Paid Holidays.
Parental Leave.
Equity.
Monthly Wellness Reimbursement.
Monthly Lunch on Legion.

About Legion

Legion Technologies delivers the industry’s most innovative workforce management platform. Our mission is to turn hourly jobs into good jobs. We enable businesses to maximize labor efficiency and employee engagement simultaneously.

For more information, visit https://legion.co.

Equal Employment Opportunity

Legion Technologies is an equal-opportunity employer. All qualified applicants will be considered for employment without regard to race, color, religion, sex, age, disability, marital status, familial status, sexual orientation, pregnancy, genetic information, gender identity, gender expression, national origin, ancestry, citizenship status, veteran status, or any other legally protected status.

Disability Accommodation

For individuals with disabilities who need additional assistance at any point in the application and interview process, please email recruiting@legion.co.

Note: All Legion recruiting email communications will come from the @legion.co domain.

Legion: Principal Product Manager, Agentic AI