Forward Deployed Engineer

Middesk•San Francisco, CA

11d

About The Position

Middesk is seeking a Forward Deployed Engineer (FDE), a highly technical individual who excels at the intersection of engineering, product, and customer challenges. This role involves collaborating closely with customers and internal teams to design, implement, and refine critical integrations and AI-driven systems. The FDE will write code, manage complex deployments from start to finish, and contribute to establishing best practices for system development and operation at Middesk. This position is suited for individuals who enjoy direct customer impact, ownership, and building systems with immediate feedback loops, influencing both product usage and future development.

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.
Strong communication skills—able to articulate trade-offs clearly to engineers, product, and non-technical stakeholders.
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.
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 Haves

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

Responsibilities

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.
Establish patterns and standards for other engineers.
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.
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.
Run multiple coding agents or automated workflows in parallel, debugging failures, and reasoning about system behavior.
Act as a tight feedback loop between customers and core product teams.
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.
Lead through influence, setting a high standard for engineering quality and pragmatism.
Guide engineers through design reviews, code reviews, and hands-on collaboration.
Help define what “great” looks like for Forward Deployed Engineering at Middesk.