For the CEO of SafeWay Driving, Being a Leader Starts With Not Being Afraid to Have Your Voice Heard

While working at a small restaurant as a teenager, Ann Littmann was given a piece of advice that continues to influence her work ethic to this day: Never sit still—keep working to make your life better. It was one of the restaurant’s cooks who told her that. He’s since left the restaurant industry, working his way up from line cook to an esteemed law school graduate.  

Today, it’s clear that unassuming bit of guidance has paid off in a big way—at just 28-years-old, Littmann is the young CEO leading SafeWay Driving forward.

“It’s amazing how the seemingly small moments stick with you. I was only 13 when I received that piece of advice. But today, I can look back and say that it truly prepared me for every role I took on after that,” Littmann said.  

Before taking the helm at SafeWay, Littmann first started as an intern. Armed with a degree in broadcast journalism, she graduated college at a time when the economy was struggling and jobs were hard to come by. That’s when she ran into the former CEO of SafeWay in Houston. He was inspired by Littmann's drive and vision, and he decided to create a position for her so he could bring her on board. This was back in 2011, and Littmann has been with the company ever since.

“Like any new college graduate, I had these grand ideas of what my dream job would look like—of course, a driving school wasn’t exactly the first thing to come to mind. But I was enamored with what SafeWay was doing. After hearing the passion the CEO had for the company, and learning about the vision he had created for saving lives and making a difference, this perception of what I thought a dream job should look like was completely shattered,” Littmann said. “It was an incredible opportunity. And nearly six years later, I can still say there’s nothing I would have done differently.”

Founded in 1973 by Houston Memorial High School’s football coach Gene Walker, the brand was built on a unified mission to keep drivers safe on the road. Coach Walker saw that many teenagers lacked the kind of sophisticated training and instruction that they deserved before getting behind the wheel. To fill that void, from day one, SafeWay set out revolutionize and transform the driver’s training industry.

When Littmann came on board, SafeWay was still very much a mom-and-pop company. Classrooms were in the back of the corporate office. Records were kept in giant binders, creating a complex filing system. Students would sign up for times on a sheet of paper. And with five locations at the time, each classroom felt isolated, and there was no way for any of them to communicate with each other. Noticing room to improve and streamline its operations, Littmann worked alongside SafeWay’s team to help them shift from a brick-and-mortar, paper-based classroom to a purely digital learning experience. The end result was the launch of SafeWay’s proprietary web-based system. Eventually, the company took its entire curriculum and packaged it up into an online offering. And by 2014, SafeWay went completely digital, closing down its physical locations. That same year, the brand announced that it would begin franchising. It was a huge step forward for SafeWay and for the industry as a whole, Littmann said. It was also a huge moment in her professional career, too.

“There was a lot of benefit in working at such a small company—it allowed me to have my voice heard. Being so young was a big challenge initially. I came on board with only a year’s worth of work experience, and that created a lot of self-doubt. But I was lucky in that the leaders of the company supported and lifted up the talent on their team. They encouraged me and my ideas. They made it so I didn’t have to be afraid to take initiative and pursue my ideas,” Littmann said.

Being a female leader in a male-dominated industry, this lesson has proven especially important over the years. For many women, there’s long been a fear that speaking up and voicing your opinion will come off as negative and pushy. Littmann admits that she’s had that same worry, and she works hard every single day to fight against that stigma.

“As a young woman, I had a fear of being viewed as a jerk in the office. I think that’s because we’ve been conditioned to believe that women leaders are often these villainous characters,” Littmann said. “That couldn’t be further from the truth. Just because you’re in a high position, it doesn’t mean you don’t have a personal life. It also doesn’t mean that you’ve had to step on people along the way. Breaking down that stereotype and that fear starts with taking a seat at the table—and not being afraid to truly own it.”

Today, Littmann is focused on owning her new role as CEO. Her goal is to continue expanding the brand’s reach throughout its home state of Texas. And, of course, helping to keep the roads safer along the way. To make this happen, Littmann plans to do exactly what SafeWay’s old CEO did for her—believing in each person’s unique strengths.

“From the very beginning, my leadership style has always focused on relationships. Learn to leverage each other’s strengths. Encourage everyone to work together,” Littmann said. “I have the title of CEO, but it’s something I earn every single day. It’s not an individualized effort. A true leader is someone who leads from the front—they don’t order people from behind telling them what to do. And when you’re all rowing in the same direction, working to reach the same goal, I believe that anything is possible.”