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. KEY TAKEAWAYS 00:00 A proven track record of handling volatility beats the best pedigree. 01:21 From hedge fund pricing desks to Chief Digital Officer of Insomnia Cookies. 05:10 How founder Seth Berkowitz built Insomnia Cookies out of a Penn dorm room. 17:59 How David measures success as a digital leader: speed from spotting a trend to acting on it. 24:09 How AI rewrote the return-on-investment math on shipping new software. 28:49 Why David chooses candidates with adversity over pedigree. 31:48 The interview question that separates people who own setbacks from people who blame them. 34:11 The group interview built on radical candor, and why it was so uncomfortable. 42:43 The AI-planned vegetable garden that failed, and expertise versus perceived expertise. 50:58 Where David watched the Knicks win it all, and why he stayed calm. Thank you for listening to "Hire Learning with Oz Rashid." Don't forget to leave us a review and subscribe so you don't miss out on future episodes. Connect with our host, Oz Rashid, on LinkedIn: https://www.linkedin.com/in/ozrashid. To learn more about MSH, visit https://www.talentmsh.com. RESOURCES MENTIONED "Elon Musk" by Walter Isaacson (referenced by Oz): https://www.simonandschuster.com/books/Elon-Musk/Walter-Isaacson/9781982181284 Claude (referenced by David as a design and prototyping tool): https://claude.ai #TalentAcquisition #HiringStrategy #AIinHR