Itamar Assaf
The Great Illusion of Entrepreneurs: Why Does Your Startup Get Stuck in Corporate Committees?
One of the things I enjoy most about our community is meeting people who sit at the most painful seams of the economy. This week I hosted a conversation with Itai Green, someone I met right here in our community.
Itai isn't "just another consultant." While most of the local market talks to itself, Itai has built an unusually global network. He works with giant organizations and governments - from Europe, through Brazil, to Japan - and serves as a bridge between hungry, fast-moving Israeli startups and traditional corporations that move slowly but know that if they don't adopt technology, they'll simply disappear.
These days he's also releasing his new book in the US, "Innovation or Elimination," and we sat down to talk about how you actually crack working with a corporation.
The Gap Between the Pitch Deck and the Invoice
Itai has been a startup founder who ate plenty of dust, and also an executive at corporate giants like Elbit and Amadeus. Drawing on that experience, I asked him what the biggest illusion is for a young entrepreneur walking into a sales meeting with a traditional corporation.
His answer was sharp: "The biggest illusion is the distance between the first meeting and the first invoice. An entrepreneur shows up, delivers a great pitch, and expects rapid progress. In practice, the corporation isn't buying technology - it's buying a solution to a business problem, inside a tangled system of politics, processes, and risk. If you don't understand who makes the decision, who's affected by it, and what the internal interests in the organization are - you're simply not in the game."
How Do You Get to a 60% Success Rate on Pilots?
Corporations love talking about innovation, but most projects get stuck at the presentation stage and die in committees. Itai, by contrast, reports over 60% success in technology rollouts. I asked him bluntly what he does differently, hands-on.
"The methodology is a focus on buy-in and execution," he explains. "First of all, I make sure to bring in a strong internal sponsor within the organization. Without that, there's no chance." (And I'll add from my own experience - you can move the world and do amazing marketing, but without a champion pushing from the inside, nothing will happen.)
"Beyond that," Itai adds, "a pilot has to be short, focused, with clear KPIs and a clear path to full rollout. I do significant work getting management on board to make sure it stays results-focused."
In a World of AI - Whoever Moves Slowly Simply Disappears
How can a heavy corporation - say, an insurance or agriculture company - keep pace with AI without the technology becoming obsolete before they've even finished the spec document?
"Most of the smartest people don't work for your organization, no matter who you are," Itai says. "The solution is open innovation. An organization has to work with outside startups. Instead of year-long projects, you run pilots that take weeks. You use existing solutions instead of building in-house."
The Elephant in the Room: Israeli Tech During Wartime
It was impossible to talk about global activity without touching on where things stand today. Itai shared with painful honesty: "When the smear campaign started, everything almost stopped. People simply stopped answering. Only now are we starting to see a slow return of clients."
In the same breath, he shared a story that left me with chills - about an Israeli startup he brought in at the start of the war to help identify the wounded and the fallen. The political system didn't recognize them at first, but their technology ended up delivering an incredible response to the hardest human challenge there is. "Every time I tell this story, I well up," he shared.
Rapid-Fire to Wrap Up
Before wrapping up, I ran Itai through our rapid-fire questionnaire:
A red flag telling an entrepreneur to walk away from a deal: "Slow response times and no clear support from corporate management."
The secret to presenting to a tough board of directors: "Talk business, not technology. Present success stories that are relevant to them."
Your everyday AI tool (besides ChatGPT): "NotebookLM, it helped me a lot with the book."
Itai is always looking for three things: corporate executives who understand they have to move, entrepreneurs who want to break into large organizations, and ecosystem partners. If you're sitting on a real pain point in your organization, or you have a solution that's production-ready - talk to him, he's right here with us in the community.
