Head of Delivery

Job Description

Job Description

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 and deserves better. 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 Culvers. We are a high growth series B company and quickly expanding our product portfolio to deliver on our vision. We are backed by legendary VCs and industry experts like Founders Fund, BOND, and Coatue.

Grow With Us

We are a team from UC Berkeley, Cornell, SJTU, Cambridge, NUS, with broad industry experiences from Tencent, Alibaba, Amazon, ByteDance, and more. Our engineering team is composed of passionate, driven, and talented engineers who focus on building and innovating cloud technology solutions that empower local businesses to thrive and better serve the deskless workforce in their communities. We are seeking a talented Software Engineer (Full Stack) to join our growing engineering team.

Day In The Life

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 3 days a week in-office to support close cross-functional collaboration.

Who You Are

• You have personally built and operated at least one AI agent or agentic workflow in production. You can clearly explain how it worked, where it failed, how you evaluated it, and what you kept deterministic or human-led.
• You have led a technical team, including hiring or developing people and making difficult architecture and delivery trade-offs.
• You have served customers directly—from discovery and workflow mapping through launch, problem resolution, and measurable outcomes.
• You have personally owned delivery economics—a cost model, a margin, or a capacity plan you ran and defended—and you can hold a deal-acceptance line against commercial pressure using the model.
• You can break a messy service into deterministic steps, agentic decisions, human judgment, exception paths, and escalation rules—and define how each part will be tested.
• You know how to prevent plausible but low-quality AI output from reaching customers through grounded context, constrained actions, verification, evals, review, and monitoring.
• You productize by instinct: you have turned bespoke customer work into reusable systems, and you can say no to customization that breaks the economics.
• Experience operating in a regulated domain (payroll, payments, tax, benefits, labor compliance, fintech ops) is strongly preferred.
• A forward-deployed leader, founding engineer who owned delivery economics, or technical services leader from a regulated-operations business may fit well, but demonstrated experience matters more than title.
  

What We Offer

• A mission-driven and value-based company dedicated to empower deskless workers and local businesses
• An 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. We pay 95% of your premiums for our employees and 85% for dependents
• In office amenities and stocked kitchen
• 401K Plan 
• Pre-tax commuter benefits
• Flexible PTO