Senior Forward Deployed Engineer (Enterprise AI)

• As a Forward Deployed 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
• If you’ve built AI that works in the real world and want to do it again at much higher stakes — with better data, closer lab relationships, and a founding team that moves fast — this is the role
• 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 forward-deployed team scale output without sacrificing quality
• Surface insights from deployments that inform Handshake’s platform and product roadmap

Benefits

• Health Insurance: Comprehensive medical , dental, and vision coverage
• Fertility and family forming: Through a partnership, Handshake offers comprehensive family benefits, including infertility treatments and a $15K stipend, to its employees.
• LGTBQ+ coverage: All medical plans cover transgender services.
• Mental health: Discounts on a variety of wellness apps and an Employee Assistance Program with access to five free counseling sessions.
• Tax savings: Tax-advantaged benefits to save money on healthcare, dependent care, and other expenses.
• Life & disability insurance: Essential benefits and automatic coverage with basic life insurance, plus short-term and long-term disability coverage.
• 401k match: Dollar-for-dollar match up to 1% of pay, with a max of $1,200 per year.
• Equity: Our equity program includes grants at hire, refresher grants after two years of tenure, and grants alongside promotions.
• Financial management: Handshake partners to provide free professional financial planning services.
• Learning & development: Employees are provided with an annual stipend to use towards professional development, career development workshops, manager trainings, and 1-on-1 coaching through external partnerships
• Community leader support: Employee Resource Group leaders are compensated with a quarterly bonus for the high-impact work the role requires
• Parental leave: Leaves of 16 weeks for birth-giving parents and 10 weeks for non-birth-giving parents; the policy applies to adoptions as well. Handshake also partners to provide one-on-one coaching on preparing for leave and coming back from leave
• Flexible time off: No accrued time off or waiting period to take vacation. Two paid flexible holiday days off to observe holidays that closely align with religious, cultural, and personal needs
• Sabbatical: Paid six-week sabbatical to recharge and reset beginning at six years of continuous, full-time employment, and every four years thereafter
• Volunteer time off: Two days off for social and civil activism, volunteer work, and/or any related activities, including attending and participating in protests- Strong understanding of agent architectures, evals, and how to measure and systematically improve AI performance
• Real-world experience building and shipping AI applications in production — not just fine-tuning or prototyping
• Comfort working directly with enterprise customers in ambiguous, high-stakes environments
• Strong systems thinking — you can zoom out to the business problem and zoom in to the technical solution without losing either thread
• 5-6+ years of engineering experience, full-stack with strong backend depth
• Strong communication skills — you’ll be in the room with senior stakeholders regularly and need to earn their trust quickly
• High ownership mentality — you care about outcomes, not just outputs
• Background at a company with a forward deployment or field engineering model
• Familiarity with enterprise security requirements, VPC deployments, or on-prem configurations
• Experience building multi-agent systems in production
• Domain expertise in a specific enterprise vertical (recruiting, finance, ops, legal, etc.)
• History of building evals infrastructure or AI quality measurement tooling