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4 Keys to Kelly Wade's Rise From Stacking Levi's to Trailblazing CEO

Guest: Kelly Wade, a coach at CEO Coaching International. Kelly has nearly 30 years of sales, marketing, and management experience. She spent the last decade with one of the largest commercial roofing companies, where she helped grow the business, transition the company to an ESOP as the COO, and lead the company through a highly successful sale to private equity as the first female CEO in the national roofing industry.

Quick Background: For many entrepreneurs, becoming the CEO is a natural — and often necessary — extension of leading a new company from startup to BIG. For others, becoming a CEO is the culmination of a journey from the ground floor of a business all the way up to the C-suite that develops character, skillsets, perseverance, and a unique appreciation for how high-performing teams work.

On today’s show, Kelly Wade discusses the accumulation of work and life experience that helped her grow into a successful and trailblazing CEO. 

How to Grow into the CEO Role, From Kelly Wade

1. Listen to mom and dad.

We learn some of our most important lessons about money and business at a young age. Kelly got a more in-depth education than most because her family owned a clothing business and hotels. “Those were my second homes,” Kelly remembers. “After school, I would walk down the hill from the Catholic school, stop and get fresh roasted peanuts, and go to the store. I went from stacking Levi’s and red bins to eventually working at the cashier and checking people out.”

Among the lessons that Kelly learned from the family businesses were:

  1. Right or wrong, the customer is always right. “My dad wasn’t the first to say it, there were other retailers like Ritz and Marshall Fields who are known for that quote, but that certainly was something my dad believed in.”
  2. If we’re at the store, then we’re open. “Even after hours, people would knock on the door and we opened the door. Or we would be home, my dad would get a call, and he would go to the store to make sales.”
  3. Get to know everyone. “There wasn’t a person that came into our store that my dad didn’t get to know personally. That certainly resonated with me. And as a leader I could proudly say at least one personal thing about all the employees I had.”
  4. Don’t nickel and dime. “In our clothing business, that meant free alterations and holiday gift wrapping. Those little things add up to a lot and really create a unique differentiation. That idea can be applied to any business.”
  5. Just one more thing … “There’s always one more tie, or another pair of socks. There’s nothing wrong with a little bit of upselling. All they can do is say no.”

2. Never be afraid to try to grow.

Kelly carried her family’s entrepreneurial spirit with her when she started her own corporate climb in her 20s at North American Roofing. She brandished her reputation as “The Fix-It Girl” by identifying problems and working towards solutions herself.

“I just never waited for anybody to ask me for help or waited to ask if I could do something,” Kelly says. “I would see things that needed to be fixed and want to make them better. I would try and I wasn’t afraid to fail and ask people smarter than me their perspective on things. I got so much diverse experience within the same company. Lots of learning, mostly by watching and just being around people smarter than me.”

Kelly’s experience at this stage of her career wasn’t much different from the startup CEO who has to immerse herself in every facet of the business just to get it off the ground. All CEOs need to retain that sense of curiosity about their company, their competition, and broader trends that could affect their business, even as they learn to delegate many of those details.

But Kelly was also learning how to be a can-do CEO, a leader who doesn’t feel boxed in by limitations and isn’t afraid to step outside of her comfort zone. She credits that boundless perspective for helping her step into the C-suite. “How I got there was seeing things that could make the company better,” Kelly says. “I would just try and put things together and pull people together and ask tons of questions. It’s better to just work on it and come out with the improvement versus talking about it.”

3. Make the role your own.

“In the beginning, I enjoyed the COO position more,” Kelly remembers, “because I like to roll up my sleeves and get down in the trenches. I get excited about change and new things, and I want to celebrate all the wins. And in the CEO role, I spent more time than I maybe wanted to with the CFO and the board. It was positioning, lots of interviews, and dinners with strategic partners. It took me away from that day-to-day energy of people and building something and growing.”

Eventually, Kelly embraced the number one job perk that so many CEOs overlook: you’re the boss! You run the business, not vice-versa. If the job isn’t giving you time to do the work you most enjoy doing, to grow, and to care for yourself physically, mentally, and spiritually, then rip up your schedule and start over.

Kelly says, “I created this ‘walkabout’ that allowed me to high five people, hug people, fist bump people, ask about the family. Go in the calm room that we had and do a little yoga or just share a little calm with somebody. I prided myself on being a confidant to people. I wanted that energy. And so I was able to get that on my walkabouts.”

4. Seize your moment.

Kelly believes that her transition from COO to CEO didn’t rattle other employees because everyone knew who she was, what she stood for, and how much respect she had for the company’s foundation. But she also wasn’t afraid to grow as a leader, grab the reins, and make her mark with some bold initiatives.

“I changed the whole sales strategy,” Kelly says. “I said, we’re not going to hire people who have sold roofing. We’re going to hire people who were the top salespeople in whatever they were selling. And we will train them on roofing. And so that was just earth shattering. A lot of people thought I was cuckoo, but we brought in amazing salespeople, trained them on roofing, and then we were able to grow from there.”

To make room for this influx of unconventional talent, Kelly reassigned legacy employees from management positions to training and consulting positions. She gave current and new employees alike every opportunity to succeed, but she wasn’t afraid to make tough changes when necessary.

“We had a new 90-day process,” Kelly says, “and for 90 days, I would say love ’em up. Train them, love them up. And on day 89, if they’re not ready, outta here. You learn and you just need to wait and be patient for the right person. Because man, is it costly. Just the whole disruption when you hire a wrong person. It’s a tight labor market right now, so it’s even tougher. But it’s a total mistake to hire the wrong people and to keep the wrong people.”

It can take some CEOs a lifetime to learn that delicate combination of consistency, boldness, and decisiveness. Unfortunately, your business can’t afford to wait around while you grow into its most critical role. Working with a CEO coach can give you the extra perspective and experience you need to rise to that challenge. And Kelly believes coaching could be an invaluable resource right now for women who are preparing to make the same leap that she did and take advantage of this new corporate landscape.

“There is no better time for women to be entrepreneurs, CEOs, leaders,” Kelly says. “The world is embracing remote work and true work-life balance. And for a woman, this is a great, great time. I’m not saying there aren’t amazing men who raise their children and are at pick-up and drop-off. But we have the children. There is a natural, more nurturing instinct to manage that side of the family. And even if you don’t have a family, it’s just a fabulous time for women to go out and start their own businesses and be leaders.”

Top Takeaways

1. Mom and dad know best. The things you learned around the kitchen table and while watching your parents work are a part of who you are as you grow as CEO.

2. Be your own CEO. Take control of your schedule and manage your business your way.

3. Accelerate your growth. Work with an executive coach who can help you make a BIG impact on day one.

About CEO Coaching International

CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International has coached more than 1,000 CEOs and entrepreneurs in more than 60 countries and 45 industries. The coaches at CEO Coaching International are former CEOs, presidents, or executives who have made BIG happen. The firm’s coaches have led double-digit sales and profit growth in businesses ranging in size from startups to over $10 billion, and many are founders that have led their companies through successful eight, nine, and ten-figure exits. Companies working with CEO Coaching International for two years or more have experienced an average revenue CAGR of 31% (2.6X the U.S. average) and an average EBITDA CAGR of 52.3% (more than 5X the U.S. average).

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