Head of Engineering, AI Platform

Gusto

Head of Engineering leading Gusto’s AI agents and shared platform for small-business payroll and HR services. Setting strategy, scaling engineering teams, and ensuring reliable agent operations.

Posted 8/19/2026full-timeSan Francisco • California • 🇺🇸 United StatesLead💰 $321,000 - $356,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in leading engineering teams, setting technical strategy for AI platforms, and ensuring the reliability and effectiveness of AI systems. Capable of empowering leaders, collaborating across functions, and aligning engineering efforts with broader organizational goals.

Highest-signal resume keywords

AI Product LeadershipTechnical Strategy DevelopmentLLM Agents ExpertiseCross-Functional Team LeadershipEngineering Organization Growth

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

AI Product DevelopmentTechnical ArchitectureReliability EngineeringEvaluation StandardsTool CallingRAG (Retrieval-Augmented Generation)Monitoring SystemsLangGraphVercel AI SDKFintech Regulatory Knowledge

Soft Skills

Leadership DevelopmentCommunication SkillsEmpowerment of TeamsCollaborationStrategic Alignment

Industry Keywords

AI EngineeringSmall Business AutomationEngineering StandardsNon-Deterministic SystemsAI-Native Workflows

About the role

Key responsibilities & impact

Lead AI Platform, an organization of approximately 25 engineers and its managers
Lead the technical strategy for AI agents that assist and automate work for small business owners
Set the technical direction and roadmap for the group
Define what the shared platform owns versus what product teams build independently
Lead and empower managers and tech leads
Hire ahead of organizational growth and build leadership for each team
Set engineering standards for prompts, tools, policies, evaluation, and guardrails
Ensure non-deterministic agent systems are reliable and cost-aware
Partner with product managers, designers, data scientists, product teams, and AI/ML science teams
Represent AI engineering to senior leadership
Align the group's work with Gusto's broader AI strategy
Champion AI-native ways of working and build a strong engineering organization
Report to the Head of Engineering, Core Experiences

Requirements

What you’ll need

12+ years in engineering
At least 5 years leading through other managers and tech leads
Track record of shipping AI or agent products that people rely on
In-depth understanding of LLM agents, orchestration, tool calling, RAG, evaluation, and monitoring
Ability to set technical strategy across several teams and align teams around shared outcomes
Technical depth to engage senior engineers on difficult architecture decisions
Experience growing an engineering organization
Treat reliability, evaluation, and guardrails as core engineering work
Experience leading a cross-functional group with product managers, designers, and data scientists
Ability to develop and empower leaders, communicate with technical and non-technical audiences, and work across teams
Experience across platform and product engineering, LangGraph or Vercel AI SDK, or fintech/regulatory experience is a plus
Active engagement with AI tools relevant to the role and ongoing AI fluency development

Benefits

Comp & perks

Competitive base pay
Health insurance
401(k)
Equity (RSUs)
Annual cash incentives
Benefits and compensation extras for full-time employees
Hybrid work arrangement with designated office days
Reasonable accommodations for qualified individuals with disabilities and disabled veterans
Secure, reliable, and consistent internet connection required when working outside a Gusto office