Senior Director of Technology

Location: Fort Collins, CO
Reports to: CEO
Compensation: $125,000 - $175,000

About The Flyover

The Flyover is one of the fastest-growing newsletter media companies in the country, reaching more than 5 million readers daily across a national edition, a growing slate of state editions, daily podcasts, and text messaging. The technology behind that reach—our publishing systems, audience tools, data infrastructure, and operational platforms—is built and owned in-house. As we scale, we are making serious investments in the next generation of those systems.

About the Role

We are hiring a Director of Technology to lead the engineering work that takes The Flyover from where it is today to where it is going. You will own complex, multi-quarter initiatives from messy initial concept through shipped, reliable solution, supported by a capable team of mid-level engineers and an executive group that is committed to making real bets on technology.

Your first six months will lean toward people leadership: getting to know the team, building trust, and establishing the practices that make complex work possible. From there, the center of gravity shifts to the projects themselves.

Responsibilities

• Drive Complex Engineering Projects
  • Own multi-quarter initiatives from concept to delivery. Recent successful examples include 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.
  • Scope ambiguous problems into clear, executable plans.
  • Make the architecture decisions that determine whether the work succeeds or stalls.
  • Stay close enough to the technical work to guide the team through hard parts, review key designs, and unblock when needed.
  • Own the quality of the output across the team’s portfolio.
• Shape Technology Strategy
  • Develop the technology roadmap in partnership with executive leadership.
  • Evaluate and adopt technologies that improve performance, reliability, and scalability.
  • Lead architecture decisions across services, data pipelines, integrations, and cloud infrastructure.
  • Maintain strong security and data hygiene practices across what the team builds.
• Lead and Grow the Engineering Team
  • Manage four mid-level engineers directly. Coach them, develop them, raise the bar on how the team operates.
  • Hire thoughtfully as we scale.
  • Establish development standards 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 communicate tradeoffs honestly.
  • Operate on a “no surprises” standard with executive leadership.

Requirements

• Years of progressive engineering experience, including a track record of leading complex multi-quarter projects from idea to production.
• 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 depth in Python, SQL, and web frameworks (FastAPI, Flask, or similar).
• Cloud infrastructure experience (AWS preferred).
• Experience designing scalable systems and making sound architecture decisions.
• Excellent communication skills with both technical and non-technical partners.

Nice to Have

• Experience with Apache Airflow or similar ETL workflows.
• Machine learning systems experience.
• Async programming experience.
• DevOps and CI/CD workflow ownership.
• Experience in media, publishing, or other content-driven environments.

Our Stack

• Python (primary), SQL
• FastAPI, Flask
• Internal REST APIs
• Apache Airflow
• AWS (EC2, Lightsail, Cloudfront)
• Claude Code and OpenClaw

Benefits

• Lead the technology work that shapes one of the fastest-growing media companies in the country.
• Real authority over how complex problems get solved, with a leadership team that wants the bets made.
• A team that already ships reliably and is ready to take on harder work.
• In-house expert legal counsel to navigate changing privacy law.
• A workplace that values direct communication, accountability, and continual development over bureaucratic overhead.