Buying more software will not fix broken processes.

In this episode of the Iron Bird Podcast, Dan Harris sits down with Greg Jarrett, CEO of Stack Aero, to unpack why aviation companies struggle with technology adoption and what separates useful software from expensive shelfware.

Greg has worked on both sides of the industry, first as a charter broker and now as a software founder building systems for business aviation operators and brokers. That perspective gives him a rare view into why many tech implementations fail.

The conversation explores the realities of building software for business aviation, where schedules change by the minute, every operator has different workflows, and no two companies run exactly alike.

Greg explains why operators should stop chasing shiny software tools and instead start by identifying the actual operational bottlenecks inside their business. From CRM systems and customer data to onboarding, automation, cybersecurity, and AI, this episode breaks down what aviation businesses should focus on to leverage technology effectively.

If your company is scaling, drowning in spreadsheets, or considering new software, this episode offers a practical framework for making better decisions.

✈️ Key Topics Covered

• Why aviation is uniquely difficult to build software for

• The 80/20 rule of buying software

• Why most operators buy tech before defining the problem

• How CRM-first systems improve customer experience

• Common signs your current systems are holding you back

• Why spreadsheets become dangerous at scale

• Data duplication and reporting issues inside growing companies

• Best practices for onboarding new software successfully

• Cybersecurity essentials for aviation businesses

• How AI is changing software development and internal operations

🔍 Why This Episode Matters

Technology should make your business more efficient.

But in aviation, many companies end up with bloated software stacks, disconnected systems, and more operational friction than before.

This episode explains why.

Greg breaks down the reality that software only works when paired with strong internal processes, leadership buy-in, and clear operational goals. He also shares practical advice on how operators and brokers can evaluate software, improve adoption, and avoid common implementation mistakes.

For any aviation company looking to scale, modernize operations, or improve the customer experience, this episode provides a clear roadmap for using technology strategically rather than reactively.

🤝 Episode Sponsors

• ✈️ Charter Flight Support

  The only coverage in private aviation that protects you when an aircraft's mechanical issue stops your aircraft from flying.

  Charter Flight Support not only provides financial protection when replacement aircraft cost more, they also help locate and secure quality backup aircraft fast.

  Learn more at CharterFlightSupport.com and subscribe to The Fix newsletter for real-time insights on private jet trends, aircraft types, and rates.

• 📺 Video Valet

  If in-flight experience matters, Video Valet delivers.

  With access to over 1.2 million movies, shows, magazines, and newspapers, Video Valet provides fully customized iPads for private aircraft without the need for expensive Wi-Fi or additional hardware.

  Mention Iron Bird and receive one free, fully personalized iPad with your setup.