Head of Delivery, AI-Native Services

About the role

Workstream is building AI-native services that deliver completed business outcomes. These are mature, proven service categories that businesses already pay for today. Our bet is a new cost structure: AI agents plus a small human review layer, delivering the same outcome at materially better margins than the traditional human-delivered alternative.

The business runs as two peer seats. The Head of GTM owns pipeline, pricing, packaging, and closing. You own the delivery system and the cost structure: the agents, integrations, evaluations, human review, exception handling, and compliance controls that make the margin thesis true—and the cost per completed service unit that proves it. Gross margin is a shared scorecard number for both seats. The mandate is deliberately narrow: one service, taken from design customers to repeatable, profitable operation, before anything else. This is a hands-on leadership role—you architect and build, not just direct.

This is a full-time, hybrid position with 1 to 2 days a week in-office to support close cross-functional collaboration.

Responsibilities

• Architect and build AI agents and agentic workflows in production.
• Lead a technical team, including hiring, developing people, and making architecture and delivery trade-offs.
• Serve customers directly—from discovery and workflow mapping through launch, problem resolution, and measurable outcomes.
• Own delivery economics, including cost models, margins, or capacity plans, and defend deal-acceptance lines against commercial pressure.
• Break down messy services into deterministic steps, agentic decisions, human judgment, exception paths, and escalation rules, and define testing for each part.
• Prevent low-quality AI output from reaching customers through grounded context, constrained actions, verification, evals, review, and monitoring.
• Productize bespoke customer work into reusable systems while maintaining economic viability.

Requirements

• Personally built and operated at least one AI agent or agentic workflow in production, with clear explanations of its operation, failures, evaluations, and human-led components.
• Led a technical team, including hiring or 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.
• Owned delivery economics—a cost model, margin, or capacity plan you ran and defended.
• Ability to break a messy service into deterministic steps, agentic decisions, human judgment, exception paths, and escalation rules, and define testing for each part.
• Experience preventing low-quality AI output from reaching customers through verification, evals, review, and monitoring.
• Instinct for productization—turning bespoke customer work into reusable systems while saying no to uneconomic customization.
• Experience operating in a regulated domain (payroll, payments, tax, benefits, labor compliance, fintech ops) is strongly preferred.

Forward-deployed leaders, founding engineers who owned delivery economics, or technical services leaders from regulated-operations businesses may fit well, but demonstrated experience matters more than title.

Benefits

• Mission-driven and value-based company dedicated to empowering deskless workers and local businesses.
• Early employee opportunity at a Series B hyper-growth startup; work with the founding team and industry veterans to accelerate your career.
• Competitive salary and equity.
• Comprehensive health coverage: medical, dental, and vision. Workstream pays 95% of employee premiums and 85% for dependents.
• In-office amenities and stocked kitchen.
• 401K Plan.
• Pre-tax commuter benefits.
• Flexible PTO.

About Workstream

Workstream is a mission-driven company building the all-in-one HR, payroll, and hiring platform for managing the hourly workforce. There are 2.7 billion hourly workers, making up 80% of the global workforce, but this market has been heavily underserved by technology. Workstream has been purpose-built for the hourly workforce from day one so that these businesses and their employees can thrive. Our customers include leading brands from multiple sectors, including Burger King, Carl's Jr./Hardee's, IHOP, KFC, and Culver’s.

We are a high-growth Series B company backed by legendary VCs and industry experts like Founders Fund, BOND, and Coatue. Our team includes alumni from UC Berkeley, Cornell, SJTU, Cambridge, and NUS, with industry experience from Tencent, Alibaba, Amazon, ByteDance, and more.

Learn more about Workstream:

• Workstream Series B Funding Announcement
• TechCrunch: Workstream Raises $48M
• TechBuzz: Workstream Featured in Funding Roundup