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by Matt Thomas

Meet Julie and Jake. They are both mid-market CEOs. Julie runs a well funded SaaS company. She co-founded the business with a close friend who has since moved onto another project. Now Julie sits alone at the top of a healthy organization with dry powder, optimistic investors, and a newly formed board of advisors. She recently graced the cover of a popular technology magazine and is celebrated as an up and coming CEO to watch. Her company consistently ranks high on national “Top Places to Work” lists. Julie’s executive team is strong and in a recent company wide leadership evaluation, the feedback was nearly unanimous. Julie’s people love her and they trust her.

Jake leads a large manufacturing operation. He bought the business from his dad 5 years ago, has tripled revenue, and recently acquired two of his biggest competitors. Privately held, the buck starts and stops with Jake. He has a reputation for being aggressive, unpredictable, and charismatic. Last year, Jake turned over half of his executive team for the fourth year in a row. Weekly he scrolls through the glassdoor reviews trying to guess which former employee posted each negative review. For the past two years he has worked with an executive coach focusing primarily on vulnerability in the workplace. He has not made much progress. Jake’s people fear him and they do not trust him.

Other than industry and origin story, what separates these two? They are both bright, driven, and eager to leave their mark on the world. Their organizations have clear vision, values, and strong financial models. From the outside looking in they would both be viewed as tremendous success stories. So what gives?