Forward Deployed Engineer
About the role
Forward Deployed Engineer who collaborates with customers and internal teams to design, build, and deploy production-grade integrations and AI-driven systems, owning complex technical problems end-to-end and translating field learnings into product improvements.
Responsibilities
- Build and deploy real systems: Partner with customers to design, implement, and operate production-grade integrations using Middesk APIs, data pipelines, and AI workflows.
- Own deployments end-to-end: Drive technical design, implementation, rollout, and iteration, making pragmatic trade-offs across speed, reliability, and scalability.
- Build AI-powered workflows: Develop LLM- and agent-based systems, including evals, test harnesses, and feedback loops to measure and improve quality.
- Solve ambiguous problems: Tackle complex customer challenges without established playbooks, working across backend systems, infrastructure, and tooling.
- Shape the product: Turn customer learnings into reusable solutions, internal tooling, and product improvements that benefit the broader customer base.
Qualifications
- 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 designing and operating APIs, distributed systems, and cloud infrastructure.
- Strong debugging skills and comfort working across the stack, from backend systems to integrations and infrastructure.
- Ability to independently own ambiguous technical problems and make sound architectural trade-offs.
- Strong communication skills and comfort collaborating directly with customers and cross-functional teams.
- Experience building or deploying LLM-powered applications, agents, or AI workflows, including familiarity with evals and common failure modes.
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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