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Salary: USD 280,000 - 300,000 / annual
Legion is building AI agents that execute workforce management work—not agents that merely describe it. The company is solving the substantial problem of software that reasons over demand, labor regulation, and employee preferences, then acts autonomously with human oversight where stakes require it. This Principal Product Manager role leads the product work to bring agentic scheduling and labor optimization from research through specification, prototype, evaluation, and enterprise deployment.
You will own the full product lifecycle for agent surfaces: determining agent scope and responsibilities, defining which tools it may call, establishing escalation thresholds, and designing the human-in-the-loop contract that protects employee pay and legal compliance. You will spend substantial time inside customer operations—district managers, store managers, labor operations, frontline employees—to identify which workflows suit agents and which do not, returning with a ranked, defensible view of where an agent creates measurable value.
Key responsibilities include agent definition (scope, tools, escalation, manager visibility); problem selection (identifying high-value workflows); human-in-the-loop contract design (autonomy thresholds, override mechanisms, audit trails, compliance logging); build quality assurance (staying engaged through implementation, using the product before release, catching drift from specification); evaluation (building and maintaining evaluation sets, holding releases when quality is insufficient); specification (writing and maintaining Functional Requirements Documents as ground truth); commercialization (partnering on packaging, metering, and pricing for agentic products); and design-partner delivery (leading enterprise pilot deployments).
This is a hands-on, technical product role. In a typical week you will write and iterate on prompts directly; stand up working prototypes of proposed agents before engineering builds anything; use agentic coding tools (Claude Code or equivalent) daily for prototyping, data analysis, and reading codebases; diagnose agent failures by reviewing execution traces; build and run evaluation sets independently; hold informed positions on retrieval design, tool-use patterns, structured output, model routing, and multi-tenant safety; and open pull requests against the codebase (prototypes, prompt changes, evaluation fixtures). You will follow model releases and framework changes, translating them into roadmap implications within days.
This is an individual contributor role with no management responsibility at present. You are accountable for what ships, not for what is specified. The role requires forming independent points of view from operational research; direction will not be handed down in detail. The environment carries genuine ambiguity—the category is being defined as the work progresses, and model capabilities shift underneath the roadmap.
REQUIREMENTS:
- 10+ years in product management at Principal level (or 7+ years at Senior level), 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 as 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; ability to anticipate what a customer's security questionnaire will ask about an LLM feature
- 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; willingness to discuss a release you delayed or stopped, what you found, and how you found it
- Judgment to recognize what current models cannot do reliably, and willingness to say so when a room expects a different answer
- Comfort working inside a codebase; ability to read code behind specifications, run it locally, and open a pull request (engineering background not required)
- Strong written communication; Legion runs on documents and evaluates candidates substantially on writing quality
PREFERRED QUALIFICATIONS:
- 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 comparable regulatory domains quickly
- Background in demand forecasting, optimization, or decision systems
- Experience building platform or authoring surfaces that customers configure themselves
- 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
SELECTION PROCESS:
The hiring process includes a practical exercise: a sanitized workforce management problem for which candidates produce an agent design (scope, tools, failure modes, human-in-the-loop contract, evaluation plan) together with a working prototype built by the candidate using any model provider they prefer. The exercise is discussed with the people the candidate would work alongside. Candidates are compensated for the time.
