Forward Deployed Engineer

About the role

We're hiring a Forward Deployed Engineer (FDE): a deeply technical builder and technical leader who thrives at the intersection of engineering, product, and real customer problems. You'll work shoulder-to-shoulder with customers and internal product and engineering teams to design, ship, and iterate 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.

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.