Senior Applied AI Engineer, Enterprise AI

About Handshake

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

About the Role

As an Applied AI Engineer at Handshake AI Enterprise, you'll embed directly inside enterprise customer environments as part of a small, expert team. You'll learn each customer's business deeply, their workflows, their bottlenecks, where the real leverage is, and translate that understanding into production-grade AI agents that measurably change how they operate.

This isn't an implementation or consulting role. You'll own the full stack: defining the solution, building and deploying agents, designing evals, and iterating until performance actually moves. Over time, you'll become a genuine domain expert in your customer's vertical and use that expertise to build AI that keeps getting better.

What You'll Do

• Embed directly with enterprise customers as part of a small deployment team, developing deep understanding of their business and workflows
• Define AI-driven solutions based on real business needs, not theoretical use cases
• Build and deploy production-grade agents tailored to specific customer use cases, owning end-to-end delivery
• Design and run evals to measure agent performance; iterate and hill-climb until results move
• Become a domain expert in your customer's vertical and use that expertise to build better AI over time
• Work closely with Product and Platform engineers on your team to ship cohesive, reliable solutions
• Establish engineering best practices, agent patterns, and reusable frameworks that help the team scale output without sacrificing quality
• Surface insights from deployments that inform Handshake's platform and product roadmap

What We're Looking For

• 5-6+ years of engineering experience, full-stack with strong backend depth
• Strong applied AI engineering experience and backend depth
• Real-world experience building and shipping AI applications in production, not just fine-tuning or prototyping
• Strong understanding of agent architectures, evals, and how to measure and systematically improve AI performance
• Comfort working directly with enterprise customers in ambiguous, high-stakes environments
• Strong systems thinking: ability to zoom out to the business problem and zoom in to the technical solution
• High ownership mentality, caring about outcomes rather than just outputs
• Strong communication skills to earn trust with senior stakeholders
• Location: San Francisco, CA | 5 days/week in-office

Extra Credit

• Background at a company with a forward deployment or field engineering model
• Experience building multi-agent systems in production
• Domain expertise in a specific enterprise vertical (recruiting, finance, ops, legal, etc.)
• Familiarity with enterprise security requirements, VPC deployments, or on-prem configurations
• History of building evals infrastructure or AI quality measurement tooling