Her Story
About Ashley
Ashley E. Romano is an AI and software development professional whose unconventional career has evolved from writing and editing into full-stack engineering, artificial intelligence, entrepreneurship, and AI evaluation. With approximately a decade of software development experience and roughly five to six years focused specifically on AI, she currently contributes to AI benchmarking and model evaluation at Snorkel AI while also serving as President of StayRele and pursuing entrepreneurial work in legal technology. Her technical expertise spans full-stack development, AI governance, LLM evaluation, AI benchmarking, software testing, and technical strategy.
Romano's transition into technology was shaped by her background in English literature, publishing, editing, proofreading, and copywriting. Rather than viewing her humanities background as a limitation, she recognized the value of language, analysis, pattern recognition, communication, and attention to detail in artificial intelligence. She expanded her technical foundation through General Assembly's Software Engineering Immersive program and MIT Professional Education's Innovation and Technology program, along with certifications and training associated with Google AI, IBM, and Anthropic. Her career has since included software engineering, technical consulting, startup leadership, and product and technology strategy. At StayRele, she has led technical development, responsible AI governance, EU AI Act compliance initiatives, and product strategy, while her legaltech work includes developing access-to-justice algorithms.
Beyond her technical accomplishments, Romano approaches her career through curiosity, continuous learning, accountability, collaboration, and respect for others. She encourages women entering technology to recognize that they do not need to know everything at the outset and that mistakes can become opportunities for growth when met with accountability and humility. Her interests also reflect her creative background, including jewelry making and entrepreneurial product development, as well as horseback riding, shell collecting on Nantucket, and spending time with friends and family. At the center of her professional philosophy is the belief that technology should be approached with both technical rigor and humanity, and that diverse backgrounds can bring valuable perspectives to the development of AI and the future of technology.
Her Interview
Ten minutes with Ashley
01What do you attribute your success to?
I attribute my success to curiosity, a willingness to learn, and the ability to approach unfamiliar challenges without assuming that I need to know everything immediately. My unconventional transition from writing and editing into software development and artificial intelligence taught me that skills from one field can become valuable strengths in another.
I have also benefited from being willing to experiment, ask for help, collaborate with others, and continue developing new technical skills. My career has continued to evolve because I have remained open to learning and taking on challenges outside of traditional career paths.
02What’s the best career advice you’ve ever received?
The best career advice I received came from a career coach after my General Assembly coding boot camp. He taught me that organizations are not simply looking for the smartest person; they are looking for someone they can work alongside every day.
That advice reinforced the importance of being human, transparent, collaborative, and humble rather than trying to convince people that I am the smartest person in the room. Technical ability is important, but the way you communicate, treat people, and work with a team matters enormously.
03What advice would you give to young women entering your industry?
It is incredibly important to be willing to learn. You do not have to know everything, and people will not expect you to know everything. Technology changes constantly, so being able to learn, adapt, and continue developing your skills is more important than believing you need to have every answer from the beginning.
You are also going to make mistakes, probably every day, and that is okay. What matters is taking accountability, learning from those mistakes, and picking yourself back up. Communicate clearly, remain humble, work as part of a team, and believe that you are good enough to be there.
04What values are most important to you in your work and personal life?
I place tremendous importance on my values. I value a willingness to learn and approach the world with curiosity. I believe in treating people the way I would want to be treated and in contributing more positivity than negativity to the world.
I also believe that everyone is equal and that we are all human. Everyone makes mistakes, and recognizing that creates space for humility, accountability, empathy, and continued growth. These values influence how I approach both my professional work and my relationships with others.
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