Forward Deployed Engineer

About the role

The Forward Deployed Engineer (FDE) role at Middesk is ideal for someone who thrives on ownership and building real systems where the feedback loop is immediate. This role bridges the gap between product intent and real-world usage, shaping both how Middesk's product is used and what it becomes.

What You’ll Do

• Own Technical Direction for Deployments
• Lead architecture and technical design for complex, customer-facing systems and integrations
• Make and communicate clear trade-offs across speed, reliability, and scalability
• Identify systemic risks and drive improvements across deployments, not just one-off solutions
• Establish patterns and standards that other engineers can build on—helping define what "great" looks like for Forward Deployed Engineering at Middesk
• Build & Deploy Real Systems
• Partner deeply with strategic customers to understand their architecture, workflows, and constraints
• Design, build, and deploy production-grade integrations using Middesk APIs, data pipelines, and AI workflows
• Own deployments end-to-end: from architecture and implementation to rollout, monitoring, and iteration
• Solve ambiguous, high-impact problems that don't yet have established playbooks
• AI, Agents & Evaluation
• 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
• Create test harnesses, metrics, and feedback loops to continuously improve AI-driven systems
• Feel comfortable running multiple coding agents or automated workflows in parallel, debugging failures, and reasoning about system behavior
• Influence Product & Engineering Direction
• Translate deployment learnings into reusable abstractions, internal tooling, and product improvements
• Influence roadmap priorities by surfacing recurring patterns, technical gaps, and opportunities for leverage
• Participate in architecture discussions and contribute to org-wide technical decisions

Core Requirements

• 6+ years of experience building and shipping software in production environments
• Demonstrated experience acting as a technical lead or domain owner for a team or major system
• Strong proficiency in Python and at least one additional language (TypeScript, Go, etc.)
• Experience designing and operating distributed systems, APIs, and cloud-native infrastructure
• Comfort operating across the stack: backend systems, integrations, infrastructure, and tooling
• Strong debugging instincts and an ownership mindset—you care deeply about failure modes, not just happy paths
• Strong communication skills—able to articulate trade-offs clearly to engineers, product, and non-technical stakeholders

Nice-To-Have

• Former founder or early startup engineer
• Experience with identity systems, risk/fraud, or workflow automation
• Familiarity with observability, reliability engineering, or system safety practices