Podcast: David Salama — The Insomnia Cookies Executive Who Hires Differently

In this episode, we talk with David Salama, Chief Digital Officer of Insomnia Cookies, about leading digital transformation at a brand built on nostalgia. David started his career pricing complex instruments at a hedge fund, then led the product side of the innovation lab at S&P Global. He went on to co-found FlyCleaners, raising more than $10 million and growing the business to 300 employees while helping build one of New York City's first on-demand companies. For the past six years, he's led engineering, product, and IT at Insomnia Cookies, scaling the company to nearly 400 bakeries across the US, Canada, and the UK. We cover how he measures success as a digital leader, why he thinks cheaper software creates more demand for engineers rather than less, his contrarian hiring philosophy, the interview question he uses to spot ownership, and the AI-planned vegetable garden that taught him the difference between expertise and perceived expertise.

Aug 12, 2026
# mins
Podcast: David Salama — The Insomnia Cookies Executive Who Hires Differently

Podcast: David Salama — The Insomnia Cookies Executive Who Hires Differently

In this episode, we talk with David Salama, Chief Digital Officer of Insomnia Cookies, about leading digital transformation at a brand built on nostalgia. David started his career pricing complex instruments at a hedge fund, then led the product side of the innovation lab at S&P Global. He went on to co-found FlyCleaners, raising more than $10 million and growing the business to 300 employees while helping build one of New York City's first on-demand companies. For the past six years, he's led engineering, product, and IT at Insomnia Cookies, scaling the company to nearly 400 bakeries across the US, Canada, and the UK. We cover how he measures success as a digital leader, why he thinks cheaper software creates more demand for engineers rather than less, his contrarian hiring philosophy, the interview question he uses to spot ownership, and the AI-planned vegetable garden that taught him the difference between expertise and perceived expertise.

Podcast: David Salama — The Insomnia Cookies Executive Who Hires Differently

Podcast: David Salama — The Insomnia Cookies Executive Who Hires Differently

In this episode, we talk with David Salama, Chief Digital Officer of Insomnia Cookies, about leading digital transformation at a brand built on nostalgia. David started his career pricing complex instruments at a hedge fund, then led the product side of the innovation lab at S&P Global. He went on to co-found FlyCleaners, raising more than $10 million and growing the business to 300 employees while helping build one of New York City's first on-demand companies. For the past six years, he's led engineering, product, and IT at Insomnia Cookies, scaling the company to nearly 400 bakeries across the US, Canada, and the UK. We cover how he measures success as a digital leader, why he thinks cheaper software creates more demand for engineers rather than less, his contrarian hiring philosophy, the interview question he uses to spot ownership, and the AI-planned vegetable garden that taught him the difference between expertise and perceived expertise.

Podcast: David Salama — The Insomnia Cookies Executive Who Hires Differently
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