2030

Cadre AI

Real talk with business leaders preparing for 2030. Uncover the strategies top executives are using to future-proof their business.

Episodes

  1. 22 JAN

    How This $2B+ Technology Company is Preparing for the Future [Ft. Elia Wallen, Engine]

    Most boards pressure founders to reduce direct reports as they scale. Elia Wallen took the opposite approach: he manages 15 direct reports while growing Engine past 1,000 employees to a $2.1B valuation, and he eliminated the Chief Product Officer role entirely. His logic: additional management layers slow decision-making when speed matters most. When you build talent density and restructure one-on-ones around problem-solving instead of status updates, you can operate with higher spans of control. That philosophy was nearly tested to breaking point. Engine came within weeks of running out of cash before their Series A with Telescope Partners closed. At the time, they had 150-180 employees across two entities. That near-death experience shaped Wallen's rejection of rigid planning. He refuses to create five-year plans, preferring to pivot quickly when new information emerges. Case in point: he publicly declared Engine would never do flights and cars, then reversed the decision weeks later. On AI, they've now automated over 50% of support cases while actually improving customer satisfaction scores—not by replacing people, but by redeploying them to higher-value work as the company doubles annually. Topics discussed: Managing 15 direct reports by focusing one-on-ones on unblocking problems and identifying blind spots Operating without a Chief Product Officer to eliminate layers between product teams and customers Nearly running out of cash weeks before Series A closed despite previous successful exits Understanding valuation multiples: 30x in 2021 versus 9-10x in 2024 makes growth more substantial than surface numbers suggest Prioritizing will over experience when hiring to find people still hungry to prove themselves Automating 50%+ of support cases with AI while improving satisfaction by overcoming legacy system skepticism Deploying AI internally first for faster iteration with immediate feedback before customer-facing rollout Building personalization and voice/chat interfaces for travel instead of traditional search experiences Establishing talent density before removing rules to enable Netflix-style freedom and responsibility Actively deleting processes and bureaucracy to keep the organization young despite reaching scale

    24 min
  • 1 Episode

About

Real talk with business leaders preparing for 2030. Uncover the strategies top executives are using to future-proof their business.

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  • Creator
    Cadre AI
  • Years Active
    2K
  • Episodes
    1
  • Rating
    Clean
  • Copyright
    © Cadre AI
  • Show Website
    2030