Advertising / Business / Career development / Hiring

From school to startup: Thoughts on making a career switch with Kapowza’s Debi Krulak

After 18 years in education, Krulak joined the Baltimore creative agency in August. Here's a look at three tips on making "the leap."

Debi Krulak joined Kapowza in August 2019. (Courtesy photo)

This editorial article is part of's Hiring Trends Month. Baltimore's NET/WORK tech jobs fair is March 4.

Debi Krulak called it “the leap.”

Over 18 years working as lower school technology coordinator at Boys’ Latin School of Maryland, she set up flexible workspace for students and led classes as they explored tech and making.

“It was a good chance to be creative, it was a good working environment. I had colleagues that I really respected,” she said. “I really liked it.”

But last year, she started pondering whether it was time for a change. When she initially took the job, it was in part because the school’s schedule was close in timing to her two then-school-age children’s schedules. And she thought back to her career before teaching, when she worked as a production coordinator in advertising and film and rose to director of client services at D.C. production company OnLine Communications as it moved into the web era.

“I had a milestone birthday coming up and I started to wonder, ‘Is this all?'” she told As she reflected, Krulak, 50, was resolved: “I think I have more in me. I think there’s something else I want to do.”

So when it came time to submit for a new contract last March at Boys’ Latin, Krulak’s wasn’t among them. It meant that she was effectively giving notice without anything else lined up for herself right away.

“That was a bit of a leap, but it paid off,” she said.

Buoyed by a sense that the right next step was out there, she reached out to local companies that appeared like they could be a fit, and interviewed. It put her on a path back to advertising by the summer — a second leap.

In August, Krulak was hired as project manager at Brewers Hill-based creative agency Kapowza. Now, after six months, she’s settled into the role as she learned the ins and outs of Kapowza’s different accounts, and how she can best serve support and carry forward the work that partners Dan Schepleng and Sean Sutherland are leading.

She has also found she is not alone in making a career switch. Krulak said talk of career switches and new roles often comes up in conversation among friends. Recently, we chatted with Krulak about some of the keys to transitioning to a different industry:

Identify transferrable skills.

Sometimes, a resume can’t convey everything, and that becomes especially true as one starts moving across sectors. As a teacher and department coordinator, Krulak gained experience overseeing equipment and reporting to administration, as well as leading the school’s robotics team. While standing in front of a class and leading client meeting are similar, the roles required look different on a resume. Krulak found that HR managers weren’t quick to make the connection.

“It takes someone with a fair amount of imagination to say, ‘She can learn the language we use … I see here she has some skills that fit in nicely, that will transfer,'” Krulak said.

In the role at Kapowza, Krulak has been able to put experience with reporting and ensuring projects stay on track to use. She also found that organization, flexibility and the desire to work on a team were important to apply. And there have been some similarities that are surprising. The ability to listen to different constituencies has been helpful in listening to clients and understanding what they want, she said.

In the end, she was motivated by a love of being around creative people, and providing the things to help them do their job well.

Use resources.

As she was looking to enter a new industry, Krulak found resources to help folks making a switch — for one, networking community Women’s Daily Post has a group that’s specifically geared toward transitions.

“One person in particular was able to help me articulate how my skills as a teacher were transferrable, so that was a really wonderful resource,” she said.

And now that she is in the role, Krulak is looking to expand her skills. With Kapowza’s support, she is entering a class on social media marketing skills through AdSkills.

Give it time.

Having a timeline in mind helped Krulak as she entered the job search. The contract process at her former employer built it in, and she knew she wanted to get a job by summer, when the school year formally transitioned.

When Krulak reached out to Schepleng, timing was also an important factor. It came shortly after he identified the need for a project manager role, and how it could help the agency.

Being a new role, there was some risk involved, so Kapowza and Krulak decided to give it a trial period. They figured it would provide a chance for Krulak to get a foot in the door and learn more about what the role and agency were like. Initially, they settled on a period of 90 days.

“Two weeks in, we both realized it was a pretty good fit,” she said.

Companies: Kapowza
Series: Hiring Trends Month 2020

Join the conversation!

Find news, events, jobs and people who share your interests on's open community Slack


‘Shark Tank’ reruns and mentorship prepared Baltimore entrepreneur for her primetime moment

Baltimore daily roundup: B-360's policy moves; a foundation's fight for financial inclusion; Digital Navigator training

Baltimore daily roundup: Johns Hopkins dedicates The Pava Center; Q1's VC outlook; Cal Ripken inaugurates youth STEM center

Baltimore daily roundup: Scenes from an epic Sneaker Ball; Backpack Healthcare in Google AI accelerator; local tech figures' podcast

Technically Media