Principal Product Manager, Agentic AI

Legion is looking for a Principal Product Manager, Agentic AI to lead the next phase of our AI-native workforce management (WFM) platform that turns hourly jobs into good jobs. Legion’s AI platform already delivers value by unifying fragmented frontline systems and processes, including forecasting, scheduling, time and attendance, and employee engagement, into a single, intelligent system of action for frontline work.

This role owns the agentic layer of the Legion platform. You will define how agents plan, act, ask for help, and escalate across web, mobile, voice, chat, and messaging surfaces. You will own the interaction primitives and primitives for human-in-the-loop collaboration, as well as the infrastructure that makes agents trustworthy in production: evaluation harnesses, simulations, permissions, guardrails, audit trails, rollback and kill-switch controls, and cost and latency budgets.

This is a senior individual contributor (player-coach) role with company-level influence. Partnering with Design, Engineering, Data Science, and Go-To-Market teams, you will shape Legion’s product direction and AI strategy. You will report directly to the VP of Product and act as a player-coach: setting strategy, mentoring other product managers on agentic product craft, and personally driving the most critical agentic initiatives from discovery to scaled deployment.

Job Overview

The Principal Product Manager, Agentic AI is responsible for defining and delivering Legion’s agentic product strategy. You will:

• Own the agent experience end-to-end, from early research and prototyping through evaluation, rollout, and optimization.
• Define human-agent collaboration models for managers and employees, including when agents act autonomously, when they recommend, when they must ask for approval, and how exceptions are handled.
• Build the agent platform foundations that enable other teams to safely ship agentic workflows: task planning, tool use, memory, context, permissions, policies, evaluations, and observability.
• Drive measurable outcomes: adoption, task success rate, time saved, schedule quality, labor optimization, compliance, and employee experience.

What You Will Own

Agent Surfaces and Interaction Patterns

• Agent experience across web and mobile (employee and manager), voice, chat, and messaging.
• Interaction primitives that make AI understandable and controllable: previews, explanations and citations, drafts, approvals, undo, overrides, and escalation paths.
• Multimodal workflows where agents can read, write, and act on behalf of users within clearly defined permissions.

Platform and Trust

• Agent orchestration patterns (single agent and multi-agent), tool interfaces, context and memory strategy, and reusable workflow components.
• Trust and safety systems for production agents: identity and permissions, policy checks, guardrails, audit logs, redaction, and incident response.
• Evaluation and quality systems: offline benchmarks, simulations, online experiments, human review workflows, and continuous monitoring for regressions, hallucinations, and bias.

Strategy

• A clear, prioritized roadmap for agentic capabilities across Legion’s core domains (forecasting, scheduling, time and attendance, communications, and engagement).
• Build, buy, and partner decisions for models, agent frameworks, voice and messaging channels, and evaluation tooling, in partnership with Engineering and Data Science.
• Cost and performance strategy: model selection, routing, caching, and latency targets that protect customer experience and margins.

Go-To-Market and Commercialization

• Packaging and rollout strategy for agentic features (beta programs, customer pilots, enablement, and adoption playbooks).
• Partnership with Sales, Customer Success, and Marketing on positioning, demos, and customer proof points, including ROI narratives grounded in evaluation results.
• Feedback loops with strategic enterprise customers to validate workflows, governance needs, and change management requirements.

What Success Looks Like (First 12 Months)

• Shipped at least two production-grade agentic workflows that are adopted by major enterprise customers and measurably improve manager and employee outcomes (for example, time saved, schedule quality, and reduced manual effort).
• Established a repeatable evaluation and release process for agents (benchmarks, simulation, canary rollout, monitoring) that other product teams use by default.
• Delivered a clear agent platform roadmap and reference architecture components (permissions, approvals, audit, and observability) that accelerate delivery across multiple teams.
• Built trusted relationships with enterprise customers and internal stakeholders; you are the go-to leader for agentic strategy, tradeoffs, and execution.

What You Bring

• 10 or more years in Product Management (or equivalent), with 5 or more years leading complex platform, workflow, or AI products in B2B SaaS.
• A proven track record of shipping AI-powered or automation-heavy products to enterprise users, ideally including conversational, copilot, or agentic experiences.
• Deep fluency in agentic product development: large language model capabilities and limitations, tool use and function calling, retrieval, evaluation design, prompt and system design collaboration, and failure mode analysis.
• Strong systems thinking: you can design end-to-end workflows across users, agents, tools, data, permissions, and policies.
• Exceptional product craft and communication: crisp problem framing, clear specifications, and executive-ready narratives. You can work through ambiguity with Design and Engineering at a detailed level.
• Customer obsession and commercial acumen: you have led pilots, navigated enterprise stakeholders (operations, IT, security, and legal), and driven adoption.

Preferred Experience

• Workforce management, HR tech, scheduling, time and attendance, labor optimization, retail or hospitality operations, or adjacent domains.
• Voice agents, contact center automation, or messaging-based workflows.
• Building evaluation, simulation, and experimentation platforms, or safety, governance, and audit systems for automated decisioning.
• Experience with regulated or policy-constrained environments (compliance, wage and hour, union rules, or fairness constraints).

What Will Make You Successful Here

You lead with outcomes and systems, not features. You can articulate a bold vision for agentic work while staying grounded in reliability, governance, and measurable impact.

You are a builder. You prototype, test, and iterate quickly, and you are comfortable moving from customer calls to technical tradeoffs to evaluation results in the same day.

You set a high bar for trust. You believe agents should earn autonomy, and you design controls, transparency, and human oversight from the start, especially when decisions affect pay, schedules, and legal compliance.

You are collaborative and influential. You align diverse stakeholders, mentor peers, and raise the bar for product quality across the organization.

Operating Values

We welcome everyone. At Legion, we embrace diversity and foster an inclusive environment where all individuals are respected and valued.

We are committed to innovation and excellence. At Legion, we function as a unified team, taking ownership of our actions. Each day presents an opportunity for us to exceed expectations and make a meaningful impact.

We are resilient in the face of change. At Legion, we take pride in helping our customers solve their toughest challenges and foster an unmatched level of trust.

We embrace an ownership mentality, holding ourselves accountable for our actions, decisions, and outcomes. At Legion, we act with urgency to deliver high-quality results.

We believe in second chances and the power of growth. At Legion, we are committed to fostering an environment where individuals can thrive and continuously improve.

About Legion

Legion is a fast-growing, AI-native workforce management unicorn that delivers the industry’s most innovative workforce management platform. Founded in 2016 and headquartered in San Francisco, Legion helps global brands across retail, hospitality, healthcare, and manufacturing turn hourly jobs into good jobs. The Legion platform is trusted by leading employers to optimize labor efficiency, enhance compliance, and improve employee engagement. Backed by leading investors, Legion continues to lead the future of frontline work.

Legion is a fully remote employer with a globally distributed team, offering flexible work arrangements, including working remotely from anywhere. Benefits include, but are not limited to:

• $0 monthly premium and other flexible medical, dental, and vision plans
• Fully paid parental leave for eligible employees and a generous maternity benefit
• Unlimited paid time off and modern leave programs
• Fully remote global team with flexible work arrangements
• Generous equity compensation
• Monthly stipends for technology, internet, wellness, and family needs
• Programs that support personal and professional growth

The base salary range for this role is $280,000 – $300,000 + Bonus + Equity. Compensation is determined by experience, qualifications, and location, and includes a competitive benefits package and equity.

Legion is an Equal Opportunity Employer and does not discriminate on the basis of race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, or military or veteran status in any employment decisions.

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