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Head of Engineering

Job in Boston, Suffolk County, Massachusetts, 02298, USA
Listing for: AutoPylot
Full Time position
Listed on 2026-03-04
Job specializations:
  • Software Development
Salary/Wage Range or Industry Benchmark: 125000 - 150000 USD Yearly USD 125000.00 150000.00 YEAR
Job Description & How to Apply Below

As an FAA-authorized UAS Service Supplier (USS), 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 Auto Pylot’s technical direction and long‑term platform architecture
  • Take over and evolve an existing production system
  • Strengthen performance, reliability, and scalability
  • 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

Auto Pylot is a modern, Type Script‑based, serverless architecture built on AWS.

  • Type Script (Node.js, ESM)
  • Serverless AWS architecture (Lambda, API Gateway)
  • Dynamo

    DB (with event‑driven patterns)
  • SQS/SNS for async processing
  • React + Ionic (mobile + web)
  • Auth0 (OAuth2 / OIDC)
  • Revenue Cat (subscriptions)
  • CI/CD via Git Hub 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 Type Script 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 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 (No

    SQL 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
  • Experience leveraging AI‑assisted development tools to increase engineer velocity while maintaining code quality and architectural integrity.
Bonus
  • Experience replacing outsourced teams with in‑house engineering
  • Experience in aviation, mapping, or infrastructure‑heavy domains
  • 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)
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