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Women of Webster Five: Kaitlyn

4 March 2026

Webster Five is celebrating Women’s History Month by highlighting some of the incredible women who make up our bank! This week’s spotlight is Kaitlyn in our Contact Center.

 

How did you get into this industry?

I entered the banking industry in 2006, right out of high school, when I started as a teller at the Oxford branch here at Webster Five. From day one, I discovered how much I enjoyed working in banking – especially the opportunity to build relationships and help people navigate important financial decisions. Over the years, my passion for serving customers and supporting my community has only grown. Banking isn’t just a career for me – it’s something I truly care about.

 

Why did you choose Webster Five?

I originally chose Webster Five back in 2006 after being referred by my neighbor. I was new to Massachusetts and decided to give it a try. I quicky realized how much I loved banking and the culture here at Webster Five.  About a year later, I decided to pursue cosmetology and eventually owned a hair salon in Marlborough.

After selling my business, I knew I wanted to return to banking. I remembered how much I had enjoyed working at Webster Five and the strong sense of community within the organization. That led me to rejoin the team in 2023. The culture here is truly unmatched – There’s a genuine sense of teamwork, understanding, and support. It feels like a close-knit community where everyone works well together and feels valued. I’m grateful to be part of an organization where I truly enjoy coming to work every day.

 

What is your favorite part about working in your field?

My favorite part about working in the Contact Center is building relationships and truly helping people. Whether it’s assisting someone with account maintenance, opening accounts online, navigating digital banking, responding to messages that come in through digital banking, recommending products that better fit their needs, or simply answering general questions, I enjoy being a trusted resource. I also love the sense of community – both with customers and within the organization. Banking allows me to make a meaningful impact in people’s lives while working alongside a supportive team that feels like family. That combination makes the work incredibly rewarding.

 

What advice would you give to women looking to grow in their career or break into their desired field?

My advice to women seeking career growth or looking to transition into a new field is to believe in your abilities and do not hesitate to take meaningful risks. Growth often happens when you step outside of your comfort zone. Seek out mentors, ask thorough questions, and remain open to learning – every experience, even the unexpected ones, help build valuable skills.

It’s also important to trust your instincts and advocate for yourself. Don’t shy away from pursuing what genuinely interests you, even if your path isn’t traditional. You’re experiences – whether within the same field or in a completely different one – can become unique strengths that set you apart. Above all, stay resilient and confident in the value you bring to the table.

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