Developing Leaders from Within: CareerPlug’s New President and CEO

In 2007, Clint Smith started CareerPlug with the simple idea that it should be easier for small business owners to make the right hires. Smith knew from experience – he was running his own small business out of his apartment.

Over the years, he’s seen it all when it comes to hiring. 

Clint Smith, CareerPlug Founder and CEO

“Hiring is hard. But when you get it right, it can create opportunities that you never imagined,” Smith says. “I’ve felt the highs of hiring an intern and developing him into an exceptional leader and the lows of hiring the wrong leader and watching it almost destroy our culture.”

14 years later, CareerPlug has grown to dozens of employees and more than 12,000 clients. And Smith credits the company’s success on all the times he made the right hires. 

One of those hires was the Director of Operations he brought on board in 2017, Jenny Leman.

Leman’s unconventional journey

Leman grew up with aspirations of being a professional drummer, even attending the University of Texas on a music scholarship. A percussionist in the Longhorn marching band, she had initially intended to major in music, but she quickly developed a curiosity for science and ended up earning her Bachelor’s Degree in Nutrition and Dietetics. 

Leman spent the first decade of her career as a Registered Dietitian, motivated by her desire to positively impact people’s lives through their health. But while she found the mission of her work worthwhile, she became burnt out after ten years in the industry. 

Jenny Leman, CareerPlug President

“Working with clients who weren’t motivated to committing to the changes I knew they needed to make in order to improve their health definitely took its toll on me,” Leman says. “I’m someone who needs to feel like I’m doing some good for the world through my work. So I knew it was time for a change.”

In 2012, Leman adopted twins and found her transition into motherhood a natural crossroads for her to examine her career going forward.  

“I decided to just completely change course. I had read a couple of books about business management and it definitely caught my interest,” she says. 

Leman’s first opportunity presented itself when she met a business owner who offered her a part-time position to run her entire franchise operation of four units. 

“I was basically assigned the role of taking four separately operating businesses and making them function as one, like one heartbeat,” she recalls.

Leman realized that in streamlining operations for a franchisee, she was able to make life better for everyone involved: for the business owner and for all of the employees at each of those locations. In this operations role, Leman had found a new way to positively impact people’s lives. She knew she was on the right path.

She would then go on to lead operations for a software company, and by 2017, her unique blend of franchise and software expertise made her a perfect fit for the Director of Operations role at CareerPlug to help build a people operating software for franchises.

The entrepreneur and the drummer

Clint Smith has always had an entrepreneurial mindset. It’s what allowed him to grow CareerPlug from a dream on his laptop into an award-winning hiring software that’s helped thousands of small business owners make the right hires. But as is often the case when businesses grow, he found his own role at the company beginning to change… and not for the better.

Smith says, “I’ve learned that oftentimes, as a company grows, founders and entrepreneurs get pulled away from the things they excel at – big picture strategy and building relationships outside the business – and instead find themselves tending to the operational aspects of running a business.”

Smith found himself spending too much time working in the business and not on the business. He recalls, “I had to do what the company needed, which was for me to step aside in some regards, and let someone else come in and do it better.”

So he and the leadership team at CareerPlug decided it was time to try a new approach to leadership that would allow Smith to take a step back from operations. They began to implement the Entrepreneurial Operating System (EOS), which prescribes a two-person approach to leadership:

  • The Visionary: EOS describes this role as “the person who had the original great idea, conceived the company, continues to look to expand the business, and pushes ideas forward.”
  • The Integrator: “The person who thrives on putting systems and processes in place to bring order to the chaos.”

Clearly, Clint Smith was CareerPlug’s visionary, but who would be the integrator? 

Smith recalls, “The Integrator role already described Jenny perfectly. But when our EOS implementer made a comparison to the integrator being like a drummer – making operations run smoothly like a drumbeat – I thought, ‘Wow, if that’s not a sign that Jenny is perfect for this, I don’t know what is!’”

In January 2021, Clint Smith transitioned out of the role of President and into his new role as CEO and Founder, where he could focus on the more “visionary” aspects of running the business. At the same time, Jenny Leman began taking on the “integrator” duties as CareerPlug’s new President.

The value of developing your leaders from within

When asked how he would have approached hiring a new President for his company if there were no Jenny Leman and he had been forced to make an outside hire, Smith responded: “I’m glad I’m not in that position.”

He recalls, “I’ve made some outside hires for leadership roles in the past. When that happened, I was hiring based on whether or not they had subject matter expertise and the right experience on paper. But ultimately, I didn’t place enough emphasis on hiring for core values. And those hires didn’t work out.”

Smith knows Leman already embodies CareerPlug’s core values and has proven it over the past four years. She’s a hands-on leader who has earned the respect and trust of her team. She’s not afraid to get into the trenches and solve client issues, giving her a level of institutional knowledge no outside hire could ever match. She’s deeply connected to the problem CareerPlug is trying to solve and her passion inspires her co-workers. And she already leads the company’s operations as steady as a drumbeat.

Does Leman have existing experience being the President of a software company? No.

But she didn’t need it. Smith believes in the value of developing leaders from within.

“One of our core values is ‘keep growing.’ I didn’t know much about hiring or software when I started CareerPlug, but I knew that I could make up for that by focusing on continuous learning and growth. We have always been attracted to hiring learners with high potential over people with more experience but a lower trajectory,” Smith says.

Leman adds, “It’s never too late to reinvent your career. Usually you can translate a lot from a previous career into your future journey.”

Growth opportunities matter for recruiting and retention

In his upcoming book, How to Hire, Smith describes how his business attracts and retains top talent with professional development and growth opportunities. 

He writes: “The best candidates are going to want to see how this position will help them grow professionally. They will often turn down a job that pays more if they see a path to growth at your company. Show them what they will learn by working with you and what a potential growth path could look like for them. This is what gets the top performers really excited.”

He believes so strongly in the importance of advertising professional development opportunities that he makes sure to communicate it in offer letters to new hires, right alongside compensation, benefits, and bonuses.

Professional development also pays dividends in the form of employee retention. When your team sees you consistently developing and promoting leaders from within, they’re reminded of your genuine commitment to their growth and are more likely to remain at your company longer.

Leman is also taking this advice to heart as she steps into her new role as President. She says, “When you hire the right people, you can trust them to do their job well. This is why it’s so important to get your hiring right. Ideally, you want to be able to hire your future leaders. And I’m excited to continue to help solve this problem for small businesses everywhere.”

Take action

If you’re managing everyone in your small business yourself, think about what you could do if someone took some of that responsibility off of your plate. What could you do if you had more time to work on the business? Start looking for leaders on your team and make a plan to develop them.

Learn how to identify the right candidates

You can’t make the right hires until you know what you’re looking for. Learn how to identify your ideal candidates using our candidate profile template.


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