Head of Delivery

Workstream Technologies, Inc. • Lehi, UT

8d • Hybrid

About The Position

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.

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 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.
• Personally owned delivery economics—a cost model, a margin, or a capacity plan you ran and defended—and can hold a deal-acceptance line against commercial pressure using the model.
• 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.
• Knows how to prevent plausible but low-quality AI output from reaching customers through grounded context, constrained actions, verification, evals, review, and monitoring.
• Productizes by instinct: has turned bespoke customer work into reusable systems, and can say no to customization that breaks the economics.

Nice To Haves

• 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.

Responsibilities

• 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.
• Architect and build the delivery system.
• Take one service from design customers to repeatable, profitable operation.
• Break a messy service into deterministic steps, agentic decisions, human judgment, exception paths, and escalation rules—and define how each part will be tested.
• Prevent plausible but low-quality AI output from reaching customers through grounded context, constrained actions, verification, evals, review, and monitoring.
• Productize by instinct: turn bespoke customer work into reusable systems, and say no to customization that breaks the economics.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed