Forward Deployed Engineer

Join Middesk as a Forward Deployed Engineer (FDE) and work at the intersection of engineering, product, and real customer problems. You will design, build, and deploy production-grade integrations and AI-driven systems, owning complex technical problems end-to-end. This role offers unlimited PTO, healthcare benefits, stock options, a 401(k) plan, parental leave, and a hybrid work environment.

• Partner with customers to design, implement, and operate production-grade integrations using Middesk APIs, data pipelines, and AI workflows.
• Drive technical design, implementation, rollout, and iteration of deployments, making pragmatic trade-offs across speed, reliability, and scalability.
• Develop LLM- and agent-based systems, including evals, test harnesses, and feedback loops to measure and improve quality.

• 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
• Ability to independently own ambiguous technical problems and make sound architectural trade-offs
• Strong debugging skills and comfort working across the stack, from backend systems to integrations and infrastructure
• Experience building or deploying LLM-powered applications, agents, or AI workflows, including familiarity with evals and common failure modes
• Strong communication skills and comfort collaborating directly with customers and cross-functional teams
• Experience designing and operating APIs, distributed systems, and cloud infrastructure
• 3+ years of experience building and shipping production software, with strong proficiency in either Python or Ruby and at least one other language (TypeScript, Go, etc.)
• Experience building developer tools, workflow automation, or reliability and observability systems
• Experience in fintech, compliance, identity, risk, or fraud
• Former founder or early-stage startup engineer