Key Takeaways

  • Alexander Taubman and Long Lake bypass the standard SaaS model, choosing instead to acquire legacy businesses like their $6.3 billion acquisition of American Express Global Business Travel.
  • Traditional enterprise software vendors focus on booking revenue rather than driving end-user results, creating a massive gap between software sales and real efficiency.
  • Software adoption fails when treated as an IT problem; as David Senra notes via Larry Ellison, operational change is a human workflow problem.
  • Long Lake never forces employees to use its proprietary Nexus AI platform, using organic bottom-up adoption as the litmus test for product quality.
  • Productivity gains from AI are directed into increasing worker pay and scaling capacity rather than cutting headcount.

The Flaw in Selling Enterprise Software

Most software founders want to build a product, charge an annual subscription, and pass the implementation headaches to the buyer. Alexander Taubman took the opposite road. With Long Lake, he acquires established real-economy businesses and embeds proprietary software directly into their operations.

The logic comes down to incentives. In a traditional enterprise sale, the vendor gets paid once the procurement team signs the contract. Whether the frontline workers actually use the tool is secondary. As Taubman puts it: “the problem with selling software is you don't actually care about what happens in the outcome. So, for us, we're very outcomes driven. We want to really actually change the way these businesses operate.”

When you own the business, software is no longer a line-item expense sold to skeptical managers. It becomes an engine for shareholder value. Taubman points to capital allocators like Henry Singleton and the Danaher brothers, who mastered operational engineering across physical industries. Long Lake couples that playbook with frontier AI through its Nexus platform. By keeping the software internal, every efficiency gain flows directly back into the company's own bottom line.

Adoption Without Executive Mandates

Buying the company gives an operator absolute authority, but Taubman refuses to use top-down orders to push software on staff. When enterprise software gets forced onto workers from corporate headquarters, workers resist, find workarounds, and resent the interface.

Senra highlights Larry Ellison's observation on this trap: “He's like it's not a software program problem. It's a human problem. It's like you can't, like there's no point in me selling something if the way you work doesn't change.”

Taubman treats Long Lake's tens of thousands of employees as internal design partners rather than captive users. If a team ignores a feature in Nexus, the product team does not ask management to enforce compliance. They rewrite the feature.

“If we have to force someone to use our Nexus platform, then the platform is not good enough,” Taubman explains. “We take an approach of our the customer are our team members.” In his view, “we don't actually force anyone to use our tools. So owning the company is really valuable in a lot of ways but not because we force people to use the tools.”

When the tools work, the economic loop closes. As Taubman notes, the ultimate goal is “deploying them into the businesses for real outcomes, i.e. faster growth, better customer experience, better team member experience, being able to pay your team members more because they're more productive, and then ultimately to your point, shareholder returns.”

What to Do With This

Audit your internal tool adoption this week. If you have to mandate that your operations team log into an internal dashboard or follow a rigid digital workflow, stop writing reminder emails. Sit next to the lowest-performing user for two hours, watch where they stumble, and strip out three unnecessary input fields from the interface by Friday.