How One Tech Leader Uses Curiosity to Navigate Career Growth and AI

As technology changes how work gets done Allysa believes that great leadership isn't about having all the answers. It's about creating an environment where people can learn, experiment, and grow together.

As a Release Train Engineer at The Hartford, Allysa helps technology teams deliver work more efficiently by connecting AI, automation, and platform modernization with a people-first leadership approach. She focuses on removing barriers, improving flow and giving the people closest to the work the context and support to make informed decisions.

That mindset has shaped her own non-linear career, too. After joining The Hartford through its Leadership Development Program, Allysa built a celebrated career across business analysis, product ownership, and technology leadership.

“At The Hartford, leadership means being accessible, listening, and creating the conditions for people to succeed,” she tells Fairygodboss. “That spirit of support and shared purpose strengthens collaboration across teams, departments, and all levels of the organization.”

The biggest standout, she continues, is that people are “genuinely willing to help, share knowledge, and invest in one another's success.” Ultimately, she says that creates an environment where teams are “trusted to bring forward ideas, challenge assumptions, and continuously improve how we work.”

We spoke with Allysa about embracing career pivots, leveraging AI as a leadership tool, fostering high-performing teams, and why curiosity—not perfection—is one of the most valuable qualities for anyone looking to grow in tech.

Tell us a bit about your current role as a Release Train Engineer. How are you using AI, automation, and platform transformation to help teams deliver value faster?

As a Release Train Engineer, I help teams deliver value quickly and predictably by improving flow across the software delivery lifecycle. Today, that includes using AI and automation to identify bottlenecks, uncover delivery gaps, and generate ideas for improving how teams work.

Our development teams are exploring AI-enabled tools and agentic workflows to support analysis, performance optimization, and defect resolution, while we modernize core platforms that support underwriting and business operations. My role is to help connect those efforts so technology, processes and people work together to improve speed, quality, and business outcomes.

How does your leadership style show up in the way you help teams learn quickly, make decisions closest to the work, and continuously improve how they deliver?

My leadership style is centered on enabling my team. The people closest to the work are often best positioned to make decisions, so my role is to provide context, remove barriers, and help teams succeed. I encourage teams to experiment, gather feedback, and adjust rather than waiting for the perfect answer. When people have the right context, clear guardrails and trust, they can learn and solve problems, faster, and ultimately deliver better outcomes.

One strategy that's been particularly effective is creating visibility into flow and using data to drive conversations. I use approved AI tools to summarize trends, identify patterns, and surface improvement opportunities faster, which allows us to spend less time gathering information and more time collaborating to solve the right problems. The value isn't the technology alone—it comes from how we use those insights across teams to make better decisions, improve flow, and deliver value faster.

How did mentorship and internal mobility shape your career journey?

Mentorship and internal mobility have gone hand in hand throughout my career at The Hartford. Internal mobility gave me exposure to new parts of the company, and my mentors and advocates gave me the confidence to pursue opportunities beyond my current role.

I've experienced firsthand how impactful it can be when someone takes the time to offer guidance, encouragement, or simply helps you see potential in yourself before you fully see it on your own. It's a big reason I'm passionate about mentoring others today.

What makes the culture and people at The Hartford unique?

What makes The Hartford so special is its people. There is a genuine willingness to support one another's growth through mentorship, new opportunities, or simply helping someone succeed. The work matters, but the support, trust, and sense of community are what keep me here.

What is your No. 1 tip for aspiring tech leaders?

One piece of advice I received from a mentor that stayed with me was to stop focusing on whether I met every requirement for a role and instead trust my ability to learn and grow into it.

Don't wait until you feel completely ready to take the leap! Technology is constantly evolving, and great leaders don't need to have all the answers. They bring out the best in others. The strongest ideas are often shaped through collaboration, feedback, and iteration. Stay curious, seek feedback, and keep growing—you may be surprised by what you're capable of.