Success Story: Donald Benson, From Teaching to Customer Success

From the Classroom to the internet's largest and most heavily trafficked business-for-sale marketplace. Donald Benson decided to leave teaching after 10 years, leading him to join the Classroom to Boardroom Course and land a role as a customer success representative at Biz Buy Sell.

Learn how Donald used his skills as a teacher and department leader to develop a promising future in the corporate world and discover his unique insights into the teacher transition journey.

Donald’s Journey into Teaching

Unlike some transitioning teachers, Donald’s story actually began outside of the classroom and outside of education entirely.

Though he always knew he wanted to be a teacher, it wasn’t easy for him to enter the profession.

“Like a lot of kids [in college], I didn't ask for the help I needed and didn't let the school know that I had a learning disability. So, I got okay grades, but I didn't get good enough grades to qualify to get into the teaching program,” Donald said in our podcast interview.

Not sure what the next step in his career would be, Donald graduated with a double MA major and headed home.

“I managed a 7-Eleven. I worked at two different banks as a personal banker and just did different careers here and there. I stayed for a couple years and then jumped to something else,” Donald said. “And always, in my mind, I wanted to be a teacher.”

In 2011, Donald decided to go back to school and take the classes required to get his teaching license. He secured his first teaching job in 2014 before moving on to a school for the visually impaired in 2016.

“With the pandemic hitting and everything going on in the world, I realized that I didn't really like some of the things that I was doing as a teacher. And then I thought, well, maybe it's just I don't feel like I need to be in the classroom,” Donald said.

And so his teacher transition began.

“I realized that the things I Didn’t Enjoy about teaching were starting to outweigh the things that I really loved about teaching.”

Donald Benson

Testing the waters

Once Donald decided to leave the classroom, he began testing the waters of different careers.

His first role after teaching was in school administration after gaining the appropriate license. However, the role wasn’t right for him and he began looking back out into the corporate world. Not long into his search, he discovered that customer success was the right fit for him.

“It's been a blessing in disguise because I really knew I wanted to be a teacher, but then I started to see that there are certain aspects that didn't really fit me,” Donald said. “Now, I'm able to use those skills as a customer success representative.”

A guilt-Free Exit

“Something that really kind of shocks a lot of former teachers is I personally didn't feel guilty about leaving,” Donald said.

Having been in the process of starting a family, Donald was looking for a place to grow. As most of us know, once you land a role in teaching there isn’t much advancement. You can lead your team, you can take on extracurriculars, or you can become and admin. Compared to the corporate ladder, the world of teaching has only a step stool.

In our podcast interview, Donald spoke fondly of his relationship with his colleagues, students, and school community. Leaving teaching, for Donald, wasn’t the guilt-filled departure that many teachers expect.

“I was doing myself, my students, and my friends at the school a disservice by staying there and not having my heart into what I was doing.”

Donald Benson

Advice for Transitioning Educators

After delving deeper into his transition, Donald decided to join the Classroom to Boardroom Course. He was eager to learn and dove right into his coursework.

“I will tell you, invest the money,” Donald said. “Classroom Boardroom was a game changer for me. I didn't know what I didn't know.”

Despite having worked in the corporate world before moving into education, Donald had a difficult time adapting his teaching experience into corporate language. And through the Course experience, he gained a powerful network.

“There were members of Classroom to Boardroom who took my resume and read over it and they, they helped me get it to the point where it needed to be,” Donald said.

Key lessons he learned in writing a good resume included using keywords from job listings and adapting teacher language into something of interest for corporate recruiters.

Looking for more?

Listen to Donald’s full podcast episode interview on the Classroom to Boardroom podcast.

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