Head of Engineering

Job Category: Engineering
Job Type: Full Time
Job Location: Massachusetts-US Remote Vermont-US

About AutoPylot

AutoPylot is one of the largest and most trusted FAA-approved platforms for mission planning and airspace authorization for drone pilots in the United States. As an FAA-authorized UAS Service Supplier (USS)of B4UFLY and LAANC, we operate infrastructure that directly interfaces with federal aviation systems and processes a meaningful share of U.S. drone airspace authorizations every month. We are venture-backed, revenue-generating, and operating real infrastructure used by drone pilots nationwide. Now we’re bringing engineering fully in-house and looking for a Technical Co-Founder to own the next phase of platform scale.

This is not a standard engineering role. This is a builder-leader position with meaningful ownership.


The Opportunity

You will:
  • Define and own AutoPylot’s technical direction and long-term platform architecture
  • Take over and evolve an existing production system
  • Strengthen performance, reliability, and scalability
  • Lead the transition from outsourced development to internal engineering
  • Establish long-term engineering standards and best practices
  • Hire and mentor additional engineers as we grow

You’ll work directly with the founder on roadmap, product evolution, infrastructure decisions, and long-term platform strategy.

This is a hands-on role. You will be writing code.


What You’ll Be Working With

AutoPylot is a modern, TypeScript-based, serverless architecture built on AWS.

High-level stack includes:
  • TypeScript (Node.js, ESM)
  • Serverless AWS architecture (Lambda, API Gateway)
  • DynamoDB (with event-driven patterns)
  • SQS/SNS for async processing
  • React + Ionic (mobile + web)
  • Capacitor (iOS/Android packaging)
  • Mapbox (geospatial visualization)
  • Auth0 (OAuth2 / OIDC)
  • RevenueCat (subscriptions)
  • CI/CD via GitHub Actions
  • Automated end-to-end testing
  • Event-driven FAA system integrations

You do not need prior aviation experience, but you must be comfortable working in regulated, reliability-sensitive environments.


What We’re Looking For

Required
  • 7+ years building production software systems
  • Deep experience with TypeScript or strongly typed backend systems
  • Experience designing and scaling serverless or cloud-native architectures (AWS preferred)
  • Strong understanding of:
    • Distributed systems
    • Event-driven architectures
    • Asynchronous workflows
    • API design (REST)
  • Experience in making architecture decisions end-to-end
  • Experience taking a system from its current state to a materially higher scale (performance, reliability, or complexity).
  • Comfort operating in environments where uptime, reliability, and correctness matter
  • Strong database design experience (NoSQL and/or relational)
  • Ability to transition into technical leadership and build a small engineering team

Strongly Preferred

  • Experience scaling SaaS platforms from growth stage to scale stage
  • Experience working with regulated or compliance-heavy systems (fintech, healthcare, gov, aviation)
  • Experience building mobile/web hybrid applications
  • Familiarity with authentication systems (OAuth2 / JWT)
  • Experience with CI/CD pipelines and automated test coverage
  • Experience mentoring engineers or leading small teams

Bonus

  • Geospatial systems experience
  • API platform or developer ecosystem experience
  • Experience replacing outsourced teams with in-house engineering
  • Experience in aviation, mapping, or infrastructure-heavy domains
  • AI/data platform exposure
  • UAS Part 107 or another pilot’s license a plus

What This Is Not

  • Not a pure management role
  • Not a “CTO who doesn’t code” role
  • Not a corporate process-heavy environment

We are looking for a technical owner who can both design the system and ship features. This is an opportunity to build and scale infrastructure that directly interfaces with federal aviation systems and supports a rapidly growing drone ecosystem.


Compensation

  • Competitive base compensation plus meaningful founder-level equity. Structured to align long-term incentives and ownership.
  • Fully remote, Northeast preferred (U.S. only due to FAA requirements)

Apply for this position

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