Senior Director of Technology

Location: Fort Collins, CO

Reports to: CEO

Compensation: $125,000 – $175,000

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.

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.

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.

• 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.

• 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.

• 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.

• 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.

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

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

• 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.