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How I Got Here: Ashley Esposito on creating your own path in tech

The technologist and Baltimore school board frontrunner explains how using tech to cover her weaknesses became her greatest strength.

Ashley Esposito. (Courtesy photo by Shae McCoy)

This is How I Got Here, a series where we chart the career journeys of technologists. Want to tell your story? Get in touch.

Ashley Esposito, 38, didn’t graduate with her degree in software development and security until last year. But that didn’t stop her from working as an IT programmer for the State of Maryland for close to a decade, relying on coding skills she taught herself.

“I’ve always had to rely on different senses to make up for not being a strong reader,” Esposito told Technical.ly. “During that time period, I learned about databases. We had access to [the] Microsoft Access database course, and I was like, ‘Oh my gosh. This can help me because then I can automate things so that I don’t make mistakes.’”

The reason that she’s not a strong reader, had to take night classes to barely graduate high school and repeatedly (until last year) flunked out of every four-year institution she had attended was a mix of undiagnosed ADHD and dyslexia.

“Every job that I had, I was building my own databases to make my work easier and to not get in trouble for making things that people saw as stupid mistakes,” said Esposito.


Using the Visual Basic programming language, Esposito automated clerical workloads that dealt with receiving documentation and applications. She also increased efficiency to the point that she was promoted to a case manager position. She repeated this process of creating the logic and formulas in Visual Basic to automate systems within the overall case management apparatus. It got to the point that director-level employees were using her programs.

Eventually, this automation work led to a call from the main office of her state agency. They asked her to come downtown with an external hard drive of her “little databases.”

“I thought I was getting fired,” Esposito said. “Because, technically, nobody gave me permission to do that or to use the shared drive and connect all these little systems.”

Instead, they gave her a new job. The state gave her access to training and programming courses for languages like SQL and C#. Her new state government role required learning programs and sitting in workgroups to learn what a department needed so she could create databases that help manage their workloads and the policy logic.

She worked with developers doing this automation work for almost a decade until the state started phasing out her position in favor of contractors. She saw the writing on the wall and continually tried to validate her skills through a degree. But, despite her practical knowledge, she kept failing classes. 


The degree was necessary because the classified nature of government work meant she didn’t have a portfolio to show. Also, public sector tech tends to be heavily outdated compared to the private sector, so a degree was a stamp on her ability to learn the tech stacks of the private sector.

Four years ago, at her husband’s urging, Esposito finally saw a doctor that confirmed how she was neurodivergent. She had ADHD and dyslexia, but also tested really high on perceptual reasoning skills and the ability to solve puzzles and build things without instructions.

Now, she can ask for the accommodations she needs to be successful.

Esposito is currently transitioning to a frontend developer position in the private sector after about 10 years working with Maryland as a backend developer. Her new company is small and she doesn’t want to bombard them with the publicity coming from her campaign for the City of Baltimore’s school board, so she didn’t disclose it on the record. 

Here are some of the tips and advice Esposito learned along her tech journey:

  • Advocate for the accommodations you need. Don’t be stubborn and hard-headed. You don’t need to struggle through it: “I’ll be like, ‘Oh, I can read great’ or whatever. I’ll do stuff by myself and it’s just, like, terrible…There’ve been times where I’ve worked a tech job where I wasn’t able to stay because they didn’t understand my accommodations.”
  • “Nobody is going to know every programming language. It’s about mastering the ones that feel right to you.”
  • “Be flexible enough to learn new things. It’s constantly going to be changing, like the most popular in-demand languages aren’t always going to be that way.”
  • “Any company that — if part of your interview process is a culture test, or to see if somebody is a fit when we know for a fact that Black women and other groups are underrepresented — that is a huge problem.”
Donte Kirby is a 2020-2022 corps member for Report for America, an initiative of The Groundtruth Project that pairs young journalists with local newsrooms. This position is supported by the Robert W. Deutsch Foundation.
Companies: Baltimore City School Board / City of Baltimore / State of Maryland
Series: How I Got Here

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