SmartRecruiters Blog

Becoming CEO – Three Unconventional Ways

C-level employees are the top dogs. They are your boss’ boss, and odds are they’ve been good at what they’ve been doing for a long time: slowly, but surely moving up the ranks of the corporate ladder. CEO’s successes are measured by the success of their company. Do they hire the people that help their company grow? Do they know how to turn a profit? Are they social CEOs? Do they amplify the brand image the business seeks to build and maintain?


When someone tells you they’re CEO, President, or VP, you’re either intimidated, impressed or both. All that matters is, they’re in charge, right? Wrong. Do you ever stop and wonder how they got there? Not all paths to CEO-dom are predictable. These are three stories who took an unlikely path to an executive level job.


Amos Winbush III was on his way to becoming one of the artists we hear playing from our radios. Winbush had just signed a record deal, and was ready to record an album. In the midst of his new career, his iPhone crashed which resulted in the loss of tons of valuable information. It also resulted in a change of direction for Winbush. When his iPhone crashed Winbush dedicated himself to his new venture: CyberSynchs, automatic backup software for mobile devices and computers. Today, he’s CEO to a company with more that $13 million in annual revenue. From music to tech? Anything’s possible.


David Williams was in semiretirement and transitioning out of the workplace entirely when he took the job at Fishbowl, an inventory-management software provider. After experiencing a lull in product development and sales, Williams was hired as CEO to literally shut Fishbowl down. Not that fast! Williams who had agreed to a short time career as CEO decided to turn things around with the help of the Fishbowl team. It was a rocky path back to revenue, funding, and innovation but they made it under William’s helm. This CEO was hired to close a business down; instead he brought the business back and is still CEO today.

Simon Anderson
is DreamHost’s first CEO and he was elected by the people- the employees of DreamHost. Normally we think of executive placements as occurring amongst other executive level employees but not for this web-hosting and cloud-service company.  DreamHost took a cue from the Democratic System and ditched the corporate interview, allowing everyone to have a say in the next big hire. Anderson “ran” against two other prospective CEOs in executive race that consisted of video interviews, Q & A sessions, and one on ones. Like in all fair elections, majority rules and this time majority was behind Anderson.


What we learn from all three of these stories is leaders do not always get there by walking the path you would expect.

In Winbush’s case, he saw a problem and sought to solve it even if that meant a sharp trajectory from his previous path. What we learn from Winbush is, do not be afraid to take risks. If you see an issue, odds are you’re not the only on experiencing it- that’s your market.

For Williams, it’s about revival for both his career and his business. Sometimes you get hired to do one thing, but your role evolves. What we learn from Williams is if there is potential, believe in it and nurture it. Don’t settle in your job title’s roles if you think there can be more.

Anderson’s road to becoming a CEO teaches us about culture. Anderson was put through a hiring gauntlet, one that indicated very clearly what kind of culture he would be going into. Remember that skills are not everything; you will be most affective in a company where values align. Maybe you’re not a CEO yet, but a left turn could make all the difference.

Lexie Forman-Ortiz

Lexie Forman-Ortiz is the Community Manager at SmartRecruiters.