Forward Deployed Engineer

Middesk is hiring a Forward Deployed Engineer to work shoulder-to-shoulder with customers and internal product and engineering teams, designing, shipping, and iterating on mission-critical integrations and AI-driven systems that run in production. You'll write real code, own complex deployments end-to-end, and help shape how these systems are built across Middesk.

The role is a deeply technical builder and technical leader, ideal for a recovering founder or a former core engineer who misses direct customer impact. You'll set direction, influence architecture, and establish best practices for how systems are deployed and operated in the real world.

Day-to-day:

• Design, build, and deploy production-grade integrations using Middesk APIs, data pipelines, and AI workflows
• Own deployments end-to-end from architecture through monitoring and iteration
• Act as a tight feedback loop between customers and core product teams
• Build and operate LLM- and agent-based systems in real customer workflows
• Design and maintain evaluation frameworks (evals) to measure quality, reliability, and correctness of LLM outputs and agent behavior
• Influence product direction by translating deployment insights into improvements
• Lead through influence, setting high standards for engineering quality

Requirements:

• 6+ years shipping software in production
• Technical leadership experience with teams or major systems
• Strong Python proficiency plus an additional language (TypeScript, Go, etc.)
• Experience designing and operating distributed systems, APIs, and cloud-native infrastructure
• Strong debugging instincts and ownership mindset

Preferred:

• Hands-on experience building or deploying LLM-powered or agent-based systems
• Familiarity with LLM evaluation techniques (evals) and performance measurement
• Startup or high-ambiguity environment background
• Fintech, compliance, or regulated systems experience

Location: San Francisco (primary) with secondary location in New York; hybrid (2 days/week in office).