5 Successful CEOs Who Started Out in Very Different Roles

Jason Hanold
4 min readJan 11, 2024

Behind the lofty titles and exceptional achievements of some of the world’s most successful CEOs lie surprisingly humble beginnings. Some of the biggest names in the corporate world started their working lives in very different circumstances. We share the inspiring stories of five CEOs who made huge pivots in their career trajectories before succeeding in the corporate world.

1. Reed Hastings, Netflix

Before revolutionizing the entertainment industry, Reed Hastings’ first job was as a door-to-door salesman selling vacuum cleaners. Later reflecting on his experience, Hastings said he enjoyed meeting a diverse array of people and refining his communication skills.

Learning how to listen to what ordinary customers want and need helped Reed Hastings grow his career. He eventually cofounded Netflix, a company that went on to reshape the global entertainment industry. By virtue of his persistence and revolutionary ideas, Reed Hastings established the global entertainment powerhouse, transforming the way that movie and television shows are consumed by audiences all over the world.

2. Ross Cadastre, Innovative Talent Solutions Inc.

Ross Cadastre’s first career was as a professional basketball coach. The founder of Innovative Talent Solutions Inc. spent quite a bit of his free time shooting hoops growing up, citing the game as an influence on who he is as a leader today. Cadastre recalls being blown away by the teamwork and fast-paced nature of basketball, although what stood out for him was the sheer mental focus that it demanded both on and off court.

As an entrepreneur, Cadastre’s goals and ambitions went beyond business ownership. Rather, he wanted to use his mental fortitude and determination to continue in his role as a career coach and a team leader. Based in Toronto, Ontario, Canada, his company helps businesses to find the right talent to take their organizations to the next level, streamlining hiring processes and helping businesses to gain a “competitive edge in the war for talent.”

3. Terry Lundgren, Macy’s

Terry Lundgren’s original career plan was to become a vet, but it was much more academically challenging than he expected. Lundgren ended up changing his major and taking a job shucking oysters for a local restaurant to put himself through school. Lundgren’s adaptability, perseverance, and leadership skills asserted themselves, and he ended up managing the restaurant.

After completing his studies in business, Terry Lundgren made the pivotal decision to focus on the retail industry, his passion and dedication eventually leading to his appointment as CEO of Macy’s, one of America’s biggest department store chains. In his final years of tenure as CEO, Macy’s sales approached $26 billion, the company employing somewhere in the region of 140,000 employees.

4. Emily Montayed, Havenly

Emily Montayed’s first job was working as a restaurant hostess while she was in high school. Although she “didn’t love it,” Montayed concedes that the job taught her about sales skills and techniques, including how to upsell to customers. In addition, the role encouraged her to hone her negotiating abilities, particularly during the process of turning helping resolve the concerns of (previously) dissatisfied customers. Emily Montayed cites these as invaluable skills that she continues to find valuable and useful.

A former global consultant for Huron Consulting Group and American Express, Emily Montayed embarked on her entrepreneurial career when she cofounded Havenly with her sister. Based in Denver, Colorado, Havenly is a digital interior design startup offering online services. In addition to room design, the ecommerce platform also connects customers with hundreds of retailers. Clients can purchase furniture and other products after seeing a virtual representation of how they would look in their homes.

5. Richard Branson, Virgin

English businessman Richard Branson is the founder of the Virgin group, a titan with more than 4,000 subsidiaries operating in variety of industries. The flamboyant billionaire is famous for his interests in space tourism, retail, travel, financial services, communications, and technologies. According to Forbes, as of 2022, the 73-year-old’s net worth was in the neighborhood of $4 billion.

Richard Branson had a less profitable first foray in business. He founded Student magazine, dropping out of school in 1968 to promote the magazine after he sold $8,000 in advertising for the first issue. Covering everything from the Biafra and Vietnam wars to pop culture, the publication aimed to highlight the voices of young people.

Recalling its launch, Branson says his team worked around the clock, including late nights and weekends, determined to make it a success. Although the publication did not ultimately prove profitable, Branson has no regrets. He says he did not go into business with the agenda solely to make money. Instead, his goal was to shake things up in the publishing industry and make a positive difference in people’s lives.



Jason Hanold

Executive Recruiter, clients NFL, Google, Patagonia, Under Armour, Gucci, Nike, Northwestern, eBay, UFC, Vail, REI, Electronic Arts, Live Nation, #HR #Recruiter