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Workstream is a Series B HR, payroll, and hiring platform purpose-built for the hourly workforce. The company serves leading brands including Burger King, Carl's Jr./Hardee's, IHOP, KFC, and Culvers, and is 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—not just direct. The business operates as two peer seats: a 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 to repeatable, profitable operation. You will own the agents, integrations, evaluations, human review, exception handling, and compliance controls. You will define the cost per completed service unit and defend the delivery economics against commercial pressure.
You will lead a technical team, including hiring and developing people, and make difficult architecture and delivery trade-offs. You will serve customers directly from discovery and workflow mapping through launch, problem resolution, and measurable outcomes. You will break messy services into deterministic steps, agentic decisions, human judgment, exception paths, and escalation rules—and define how each part will be tested.
The role requires preventing low-quality AI output from reaching customers through grounded context, constrained actions, verification, evaluations, review, and monitoring. You will productize by instinct: turning bespoke customer work into reusable systems and saying no to customization that breaks economics.
This is a full-time, hybrid position with 3 days per week in-office to support close cross-functional collaboration.
REQUIREMENTS:
- Personally built and operated at least one AI agent or agentic workflow in production; can clearly explain how it worked, where it failed, how you evaluated it, and what you kept deterministic or human-led
- Led a technical team, including hiring/developing people and making difficult architecture and delivery trade-offs
- Served customers directly from discovery and workflow mapping through launch, problem resolution, and measurable outcomes
- Personally owned delivery economics (cost model, margin, or capacity plan) and can hold a deal-acceptance line against commercial pressure
- Can break a messy service into deterministic steps, agentic decisions, human judgment, exception paths, and escalation rules
- Know how to prevent plausible but low-quality AI output from reaching customers through grounded context, constrained actions, verification, evals, review, and monitoring
- Productize by instinct: have turned bespoke customer work into reusable systems and can say no to customization that breaks economics
- Experience operating in a regulated domain (payroll, payments, tax, benefits, labor compliance, fintech ops) is strongly preferred
- Background as a forward-deployed leader, founding engineer who owned delivery economics, or technical services leader from a regulated-operations business may fit well; demonstrated experience matters more than title
