Ilana Golan grew up “living and breathing” fighter jets and started her career as an F-16 flight instructor in the Israeli Air Force. But she was in over her head one day when a senior general came in for training.

SAN FRANCISCO — Ilana Golan grew up “living and breathing” fighter jets and started her career as an F-16 flight instructor in the Israeli Air Force.

She eventually became the first woman to be commander and in-charge of training and educating all F-16 pilots.

But she was in over her head one day when a senior general came in for training. She checked his profile and noted he hadn’t come in for a long time.

After giving him her feedback, the general stood up and said, “Honey, do you know who I am? When you were about six years old, I was bombing the nuclear plant in Iraq.”

That was when she knew she’d made a mistake.

“I realized I really don’t know my audience,” Golan told conference attendees at the “You and the Machine: Telling Stories Together” session at Inman Connect.

“Some of them were more experienced than I ever could have been.”

She said that had she known more about her customer, she would have changed not only the way she gave feedback but also everything she was doing.

The experience eventually spurred her to change the flight education program in Israel, personalize it and win her a “best commander” award.

Later, when Golan became a software engineer and entrepreneur, she came to the San Francisco Bay Area to pitch her product to two giants, Cisco and Hewlett Packard. The meetings went well, and she awaited the purchase orders.

But one decided to go with the competition, and the other opted for a homegrown, less expensive solution. What had happened?

Turns out that those she met with thought her product was great, but she hadn’t given them the tools to explain to their managers what made her different.

“I had to differentiate myself. How does my product relate to these groups?” she said.

That experience taught her that “relevant content was key,” she added. Her company eventually brought in $15 million in annual revenue.

When she founded her current company, Stiya, she knew that it would have to put relevant content “directly in front of you.” The tool uses artificial intelligence (AI) to capture traveling experiences automatically  — and it was a hit with real estate agents.

“What surprised me was I started seeing more and more agents on our platform,” she said.

“The agents would create a branded story of a house-hunting experience with a client, adding personal photos, notes on the client, videos of the school or neighborhood, and they would send a branded summary of the experience to the client.”

“They were taking Stiya and adjusting the stories to their client. And I loved it,” she added.

Stiya brought together the two stories that had been turning points in her career because in both cases, the name of the game was relevance, she said.

Email Andrea V. Brambila.

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