Cameron HeroldFounder of the COO Alliance & Invest In Your Leaders Training

The Fatal Mistake CEOs Make When Hiring a COO | Cameron Herold

14 Jul 2026 · 1 min

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Cameron Herold warns CEOs against hiring a COO just because they're overwhelmed. The role is different for every company, so the search should start by assessing what the CEO actually needs, not by copying a generic job description. Harley Finkelstein of Shopify is cited as an example of finding the right fit.

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When a CEO decides it's time to get help in the business, they may well feel overwhelmed and a little desperate. They're tempted to reach out to the first person who comes along. That's completely the wrong approach. It's unlikely to succeed, and it might well make things worse. Many of the leadership roles in business are a little cookie cutter. Most CMOs could be a CMO for most companies. Most CFOs could too. Not the COO. There are COOs who are marketing or franchise ninjas. There are COOs who would fall on their face at both, but are fantastic at finance. As Harley Finkelstein, COO at Shopify, told me on our Second Command podcast, No two COOs on the planet have the same job. That's why the search for a kickass COO doesn't start with the COO. It starts with the personality of the CEO, what they need, and the perfect match for their skills and character.