Senior Director of Software Engineering

The Flyover is one of the fastest-growing newsletter media companies in the country, delivering unbiased news to more than 5 million Americans every day. We publish a national edition and a growing roster of state editions, daily podcasts, and text messaging alerts all powered by technology and operations developed in-house. As we scale, we are investing seriously in the team and systems that make daily delivery possible at the quality our readers expect.

The Role

We are hiring a Director of Engineering to lead and develop our engineering team. You will manage a capable group of mid-level engineers who ship reliably day to day. Your job is to make them stronger, faster, and more ambitious, and to build the bench we will need as the company grows.

You will spend your first six months as a people leader: getting to know the team, raising the bar on how we work, and earning the trust of partners across editorial, sales, ad operations, and other internal groups. Once that foundation is in place, the role expands to leading complex, multi-quarter projects from ambiguous initial idea to shipped, reliable solution.

What You Will Do

• Manage four mid-level engineers directly, including weekly 1:1s, performance development, and growth planning.
• Coach the team on cross-team collaboration, prioritization, and clear communication with non-engineering partners.
• Hire to fill gaps and grow the team thoughtfully as the company scales.
• Establish development standards, code review norms, and team practices that make engineering predictable and high-quality.

Partner Across the Company

• Serve as the engineering point of contact for editorial, sales, ad operations, and other internal teams.
• Translate business needs into well-scoped technical work and set realistic expectations on timing and tradeoffs.
• Communicate priorities, progress, and risk proactively. We operate on a “no surprises” standard.

Drive Complex Project Execution

• Take ownership of multi-quarter initiatives from scoping through delivery. Recent successful examples include the development of machine-learning-driven audience segmentation, deployment of Airflow 3 to replace our aging orchestration layer, and significant build-out of agentic AI capabilities across content and operations.
• Break ambiguous problems into work the team can execute on, while staying close enough to the technical decisions to guide architecture and unblock when needed.
• Own the quality of the output across the team’s portfolio.
• Oversee the systems, integrations, and infrastructure that power daily delivery to millions of readers 365 days a year.
• Make sound architecture decisions across backend services, data pipelines, and cloud infrastructure.
• Ensure operational reliability, security, and good data hygiene in what the team builds.

What We Are Looking For

Required

• Years of progressive engineering experience, including at least one full cycle of managing a team (hiring, developing, and managing performance).
• Hands-on experience with agentic AI: building, deploying, or integrating systems where LLMs take meaningful action rather than only generating text.
• Strong technical background in Python, SQL, Docker, and web frameworks (FastAPI, Flask, or similar).
• Cloud infrastructure experience (AWS preferred).
• Experience designing and maintaining systems that run reliably at scale.
• A track record of shipping complex projects from idea to reliable production.
• Excellent communication skills with both technical and non-technical partners.

Nice to Have

• Experience with Apache Airflow (especially Airflow 3) and ETL workflows.
• DevOps and CI/CD workflow ownership.
• Experience in media, publishing, or other content-driven environments.

Our Stack

• Python (primary), PostgreSQL
• Internal REST APIs
• Apache Airflow
• AWS EC2, Lightsail, Cloudfront
• CI/CD and deployment automation

Why Join Us

• Shape engineering at one of the fastest-growing media companies in the country.
• A team that already ships well and a clear, well-funded mandate to take it further.
• Direct executive partnership and real authority over your function.
• A workplace that values direct communication, accountability, and continual development over bureaucratic overhead.

If you are an engineering leader who enjoys building teams as much as shipping systems, and you want to make complex work happen in a fast-moving environment, we would love to talk.

• Application Process: Submit your resume and a brief cover letter describing a complex project you led from initial concept to production and what your role was in getting it there.