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Workstream is building an all-in-one HR, payroll, and hiring platform for the hourly workforce—a market of 2.7 billion workers representing 80% of the global workforce. The company serves leading brands including Burger King, Carl's Jr./Hardee's, IHOP, KFC, and Culvers, and is a high-growth Series B company backed by Founders Fund, BOND, and Coatue.
You will lead the delivery system for Workstream's new AI-native services business. This is a hands-on leadership role where you architect and build alongside your team, not just direct. The business operates as two peer seats: the Head of GTM owns pipeline, pricing, and closing; you own the delivery system, cost structure, and margin thesis.
Your mandate is deliberately narrow: take one service from design customers through repeatable, profitable operation. You will own the agents, integrations, evaluations, human review layer, exception handling, and compliance controls. You will architect how messy service workflows break into deterministic steps, agentic decisions, human judgment, and escalation rules. You will define testing strategies and prevent low-quality AI output from reaching customers through grounded context, constrained actions, verification, and monitoring. Gross margin is a shared scorecard with your GTM peer.
You must have personally built and operated at least one AI agent or agentic workflow in production and can clearly explain how it worked, where it failed, and how you evaluated it. You have led a technical team, including hiring and making difficult architecture and delivery trade-offs. You have served customers directly from discovery through launch and measurable outcomes. You have personally owned delivery economics—a cost model, margin, or capacity plan you ran and defended. This is a full-time hybrid position with 1–2 days per week in-office to support cross-functional collaboration.
