Best suited to senior engineers with Python and distributed systems experience who thrive at the intersection of customer problems and technical leadership.
Derived from job-description analysis by Serendipath's career intelligence engine.
As a Forward Deployed Engineer at Middesk, you'll be a hands-on technical leader, working closely with customers to design and deploy mission-critical systems, while also influencing the broader engineering and product direction. This role is perfect for someone who thrives on direct customer impact and enjoys shaping the future of the product through real-world feedback.
Original posting from Middesk via Ashby
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.
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.
Forward Deployed Engineers at Middesk shape both how our product is used and what our product becomes.
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.
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
- 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 & Raise the Bar
- Lead through influence, not authority—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.
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.
BONUS POINTS:
- Former founder or early startup engineer.
- Experience with identity systems, risk/fraud, or workflow automation.
- Familiarity with observability, reliability engineering, or system safety practices.
WHY THIS ROLE EXISTS:
- Middesk operates in the critical path of customer systems—deployment quality matters.
- We believe engineering velocity is only valuable if it delivers customer value.
- Forward Deployed Engineers close the gap between product intent and real-world usage.
- This role helps define how Middesk builds, deploys, and scales complex systems across customers.
WHY YOU’LL LOVE WORKING HERE:
- High ownership, high trust, and real autonomy.
- Direct influence on product direction and technical standards.
- Deep technical problems with real-world impact.
- A team that values thoughtful engineering over performative process.
Source: Middesk careers (Ashby)