Experience and Hustle Can Be the Keys to the C-Suite

MBAs and CPAs look good on a CV, but real-world experience helps get you hired, according to executives.
Experience and Hustle Can Be the Keys to the C-Suite
Photo: Getty Images

As the makeup of C-suites continues to change, the opportunity to get there has become more realistic to a larger portion of people with business and finance careers. While hustle, hard work, and a little luck can pay major dividends, those who have made it to the ranks of executives at their companies have gotten there in different ways and with different expectations. 

You don’t get to [the] C-suite passively,” said John Henry, co-CEO of tech-infused auto insurance provider LOOP and former host of Vice’s Hustle, a television show focused on entrepreneurs. After selling his first company, a tech-infused dry cleaner for hit television productions like Law and Order and Boardwalk Empire, the doorman-turned entrepreneur co-founded a non-profit and then a venture capital firm. Then Henry and his team began to build LOOP, a public benefit corporation.

“Your rise to the top ranks is either through a gradual ascension or through starting your own company and building the infrastructure around you,” said Henry. “Some people learn to be CEOs; some are hard-wired that way. I am the latter. Developing [an] understanding of how you behave, why you behave that way, and when it is or isn’t serving you or your team has been the most important growth I’ve done as a leader in the past six months.”

4 Powerful Communication Strategies for Your Next Board Meeting

4 Powerful Communication Strategies for Your Next Board Meeting

This whitepaper outlines four powerful strategies to amplify board meeting conversations during a time of economic volatility. 

  John Henry

A community college dropout, Henry said he is biased in this thinking on the value of a formal education. He believes that legitimate real-world experience is some of the highest value training one can bring to an executive team in any industry.

“I have seen formal training be an incredible asset in some cases and in some professions, but generally, real-world experience is not only the best teacher, but it is also undeniably the ‘scorecard’ of success, at least in the sport of business,” Henry said.

“I’d take $100 million in annual recurring revenue over 100% on a test,” Henry continued. “As you mature, merging values and mission-alignment with depth of perspective and experience becomes key to building out a healthy organization. If everyone is learning everything on the fly, it adds a greater degree of risk to the execution.”

Henry stressed the importance of focusing on goals surrounding growth and business strategies no matter what position an individual may hold. “The C-suite title has virtually no significance in a small company. But if you can successfully grow the company, you begin to reap the benefits of having an influence on the product and business roadmaps.”

While a work-life balance is a phenomenon most employees are either actively seeking or encouraged to pursue, the insure-tech executive believes this doesn’t apply to those in an executive position.

“You can’t have your cake and eat it, too. At LOOP, we are big fans of work-life balance for everyone except the C-suite,” Henry said. “With great power comes great responsibility, [and] it is my view that you should not step into a leadership role of this magnitude unless you’re prepared to make sacrifices for the greater good of your mission,” he added.

Education Vs. Experience

While Henry’s journey is unique, the approach of building business experience outside an academic setting is not. Michelle Gilson, who is approaching her sixth month in her CFO role at biotech company Arcellx, said her journey to the C-suite has been nontraditional. It’s also built on a healthy work-life balance. Unlike Henry, Gilson thinks it’s a pivotal part of her job that her employer equips her well for. 

“I think the work-life balance tone has been set well from the top here,” said Gilson. “We work really hard and have a lot of fun doing it, but we have flexibility and support where we need it. We also have great benefits, which can help minimize wasted time.”

Time management is a skill that Gilson identifies as the most important part of maintaining a work-life balance. “I prioritize things that matter to me as a mom, wife, and executive. I’ve learned to maximize the time I have at the office and the time I have at home.”

  Michelle Gilson

Balance takes a lot of coordination in Gilson’s household. Her husband has a Wall Street career, and the couple has a toddler and a dog. “To make life work, we structure our life carefully, and we trust each other to be okay with having nontraditional family roles,” she said.

When talking about what parts of her skillset are most valuable, Gilson talked about her previous work experience as a Wall Street analyst.

“I am using the years I spent analyzing businesses and seeing the downstream impact of decisions made by management teams and applying that lens to what we are doing at Arcellx,” said Gilson. “I analyzed companies from an investor point of view. I don’t think that lens will ever go away, and I think that helps me add valuable perspectives as we grow our organization.”

While Gilson doesn’t have an MBA or CPA, her work in numerous finance positions across industries provided her the skills needed to qualify for an executive position. When asked about the value of formal education to a future executive, Gilson acknowledged how some degree programs can help build the foundation of a future decision-maker’s skillset. But she also recognized the benefit of real-world experience, especially at the time in a career when a business professional might be considering an advanced degree.

“I think there has been a focus on retaining talent in the corporate world that has helped accelerate the careers of high performers early on, which has pushed some to continue on their career path instead of pursuing advanced degrees,” said Gilson. “If a person can build a network of similar strengths outside of an MBA program, develop a disciplined thought process, and have the opportunity to learn the soft skills to lead an organization, then that person can potentially make a lot of progress in their career track in the two years they would have taken off to attend school.”

“However, not all roles will necessarily provide that,” Gilson continued. “So I can see where an MBA program could be valuable to career advancement.”

Tom Alexander, a partner in Cross Country Consulting’s business transformation practice, spoke to CFO about how executive support staff, alongside the future executives themselves, are gauging the value of education versus work experience. According to him, the most valuable knowledge to someone pushing for a career in corporate finance is already at their fingertips. 

  Tom Alexander

“The finance professional of the future will have several technology tools at their disposal, but they will need to be able to apply them to solve practical business problems and enable the right decisions,” said Alexander. “The technical options are available by acquiring robotic process automation, analytic process automation, and visualization skills, as well as understanding how to efficiently access data or obtaining a core certification in a large technology platform, not to mention the micro degrees. YouTube instructional videos have democratized these skills for those curious to learn.”

Alexander believes the makeup of the modern executive is as dynamic as it is complex; something that can’t be defined by one degree or certification.

Well-rounded executives are career-learners, according to Alexander. “They understand the complexity of highly technical accounting and capital management; the emergence of new management reporting; key performance indicators and the need to piece them together; how technologies create competitive advantage; and can evolve with the rapid change all are facing,” he said.