Forward Deployed Engineer
About the role
Forward Deployed Engineer (FDE) at Middesk, a deeply technical builder who works with customers and internal teams to design, deploy, and iterate on mission-critical integrations and AI-driven systems in production. Leads technical direction, owns end-to-end deployments, and shapes product and engineering practices with a strong customer impact focus.
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, not just one-off solutions.
- Establish patterns and standards that other engineers can build on—defining what "great" looks like for Forward Deployed Engineering at Middesk.
- 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.
- 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.
- 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, set high engineering quality standards, and mentor peers.
- Provide real autonomy and direct influence on product direction with deep technical problems.
Qualifications
- 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.
Skills
About Middesk
We make it easier for B2B companies to transact with one another
Middesk's mission is to enable every business to access the products and services they need to grow and thrive. We believe that if we can make it easy for a business to access financial products, hire new employees, and transact with other businesses, that we increase the odds of success for that business to contribute to its community and the broader economy. Our Identity provides accurate, complete information that financial services companies need to make efficient onboarding decisions. Our Agent product makes it easy for employers to file with the state and federal agencies needed to establish their business across the country. Our customers include Affirm, Brex, Plaid, Mercury, Divvy, Rippling, Gusto, and others. Based in San Francisco, CA, Middesk is backed by Sequoia Capital, Accel Partners, and Y Combinator.
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