Forward Deployed Engineer at Middesk in San Francisco, CA

ABOUT MIDDESK: Middesk makes it easier for businesses to work together. Since 2018, we’ve been transforming business identity verification, replacing slow, manual processes with seamless access to complete, up-to-date data. Our platform helps companies across industries confidently verify business identities, onboard customers faster, and reduce risk at every stage of the customer lifecycle. Middesk came out of Y Combinator, is backed by Sequoia Capital and Accel Partners, and was recently named to Forbes Fintech 50 List. 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. Forward Deployed Engineers close the gap between product intent and real-world usage—acting as a tight feedback loop that shapes both how our product is used and what it becomes. You will act as a technical leader, helping set direction, influence architecture, and establish best practices for how we deploy and operate systems in the real world. This role is ideal for a recovering founder, a former core engineer who misses direct customer impact, or someone who thrives on ownership and wants to build real systems where the feedback loop is immediate. 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. Deployment quality matters—we operate in the critical path of customer systems. • 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. • We believe engineering velocity is only valuable if it delivers customer value—your role is to make sure it does. Lead & Raise the Bar • Lead through influence, not authority—setting a high standard for engineering quality and pragmatism in a high-ownership, high-trust environment. • Guide engineers through design reviews, code reviews, and hands-on collaboration. • Enjoy real autonomy, direct influence on product direction, and deep technical problems with real-world impact. • Work with a team that values thoughtful engineering over performative process. WHAT WE’RE LOOKING FOR: 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. AI / LLM Experience (Strong Plus) • Hands-on experience building or deploying LLM-powered or agent-based systems. • Familiarity with LLM evaluation techniques (evals) and performance measurement. • Experience orchestrating automated workflows, agents, or developer tooling powered by AI. • Clear understanding of failure modes and tradeoffs in applied AI systems. Customer & Domain Experience • Experience working in startup environments with high ambiguity and rapid iteration. • Background in fintech, compliance, or regulated systems where correctness and data quality matter. • Comfortable working directly with customers on complex technical problems. 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. Compensation Range: $148K - $275K