Women on Wednesday with Kaylee Andrews

Recognizing and supporting women in technology is a top priority at Precisely. Whether it’s hosting virtual events for women to connect, or encouraging mentoring opportunities, the Precisely Women in Technology (PWIT) program goes above and beyond to ensure that women in the organization have a great network to lean on. Each month, a PWIT member is featured to share her experience navigating the tech industry. Continue reading to learn more about Kaylee Andrews, Business Operations Manager & Chief of Staff, and her experience over the last seven years.

Why did you choose to pursue a career in technology?

Before transitioning into my current role, I spent five years working as a Judge’s clerk in one of the most demanding criminal court divisions for a Judicial District in Colorado. This experience sharpened my ability to think quickly on my feet and deliver top-tier support and efficiency under pressure. However, the environment was often dangerous and emotionally taxing, as I sat through trials, processed complex cases, and interacted with difficult individuals in a windowless courtroom day in and day out.

As I began to explore other industries, I quickly realized that technology was a future-forward field where I could grow alongside it. Within my first month at Pitney Bowes (now Precisely), I knew I’d made the right choice. I started as an Executive Assistant, progressed to Senior Executive Assistant, and now serve as a Business Operations Manager and Chief of Staff. To me, the role of Chief of Staff is about being a right-hand partner and trusted advisor to senior leadership, helping them drive strategic initiatives, manage day-to-day operations, and identify opportunities for innovation. This path has provided me with endless growth opportunities, the freedom to be creative and innovate, and the chance to utilize my problem-solving prowess while fulfilling my deep desire to leave both people and processes better than I found them.

Who has been your greatest professional mentor? What’s one thing have you learned from them?

I’m very fortunate because I have the privilege of working with my two greatest professional mentors every day at Precisely. I’ve been working with, alongside, and for Greg Van den Heuvel, General Manager – Engage, and Chris Hall, CPO, since the first week I was hired seven years ago.

Greg and Chris embody the kind of leaders who lead from the ground rather than overseeing from a distance. They have never hesitated to grab a shovel and dig alongside their teams as we strive for collective growth. There has never been a task too trivial or menial for either of them to tackle, and their commitment to transparency, integrity, and empathy is truly inspiring. They foster a culture of growth and recognition, affirming team members openly and often while maintaining candor and strong lines of communication.

If I had to sum up my key takeaway from them, it would be that when honesty is at the forefront, you can always be completely candid and respectful. No matter the topic, you can maintain honesty without compromising your integrity.

What’s the biggest risk you took in your career? What was the reward?

What a great question! Over the years, I attended various webinars and trainings from other companies in the technology and software space, often seeing Chiefs of Staff or Business Operations professionals present on those calls. After researching the Chief of Staff role, I realized it encompassed many aspects of what I was trying to achieve as an Executive Assistant while offering avenues for growth.

Determined to take charge of my career path, I created a presentation for Greg and Chris, advocating for my promotion to Chief of Staff. In it, I defined the role, illustrated its responsibilities, and explained how it aligned with my current duties as an EA. I conducted thorough research and took the risk of scheduling that call to discuss my aspirations. The reward was their agreement to promote me and to assign me new projects and responsibilities that aligned with my new role.

As a woman, what challenges have you faced in the technology industry? How have you overcome them?

In the technology industry, one of the biggest challenges I’ve faced as a woman has been imposter syndrome, especially when transitioning into my role as Chief of Staff. Despite my accomplishments and the fact that my bosses never saw me as just an “assistant,” I often felt like I wasn’t fully qualified or that my success was somehow undeserved. This self-doubt can be limiting, making it hard to recognize your value and confidently step into leadership.

To overcome imposter syndrome, I’ve learned to reframe my thinking and remind myself that my role is earned, not a result of luck. I keep a log of my achievements to celebrate my wins, which helps me track my contributions and growth. I also make it a point to seek support from trusted colleagues and peers who can provide perspective and affirm my abilities. Lastly, I’ve embraced continuous learning as a strength rather than a sign of inadequacy, viewing the fast-evolving nature of the tech industry as an opportunity to keep growing. These strategies have allowed me to overcome those moments of doubt and fully embrace my role in the company.

What’s the best advice you’ve ever been given? How do you apply it to your personal and professional life?

About five years ago, during a call with Emily Wheeler (former Director of Corporate Communications at Precisely), she shared a piece of advice that has always resonated with me: “The most important conversations about you happen when you’re not in the room.” This advice served as a powerful reminder that even when our work feels very “behind the scenes” or doesn’t seem to be moving a tangible needle, that consistency, perseverance, creativity, and integrity will always be noticed.

Much of my growth has stemmed from others recognizing my contributions, even when they fell outside the expected scope of my role. This motivates me both personally and professionally to pay attention, affirm others, and ensure that the work I do reflects the professional I aspire to be—someone others would be proud to discuss when I’m not around.

What’s one piece of advice you’d offer to younger women entering the industry?

To younger women considering a career in technology, my advice is to never be the one to say no to yourself. Reflecting on the biggest risk I took in my career, many opportunities came my way because I didn’t shut myself down before even trying. If a career opportunity piques your interest, pursue it!

On paper, you might think you don’t meet every requirement—perhaps you lack certain technical skills or managerial experience—but instead of telling yourself “I’m not ready” or “I’m not good enough,” apply anyway! Push past the doubt, focus on the skills you do bring to the table, and highlight what makes you unique—your special sauce! By refraining from self-doubt, you give others the chance to see your potential, and you might just land that position or gain a new opportunity. Even if you don’t, you’ll gain invaluable experience and insights along the way.

This mindset helps you avoid self-limiting beliefs and encourages you to take risks and pursue opportunities that could accelerate your personal and professional growth!

As a successful woman in technology, what’s one thing you do to pay it forward and advocate for other women in the field?

One way that I’ve recently tried to pay it forward and advocate for other women in the field is to organize events and invite fellow females to be presenters. Just last week, I organized a Manager Summit where all of our presenters were women, including myself. This not only showcased the expertise and leadership of women in our organization but also provided a platform for them to share insights and inspire one another. By creating these opportunities, I aim to foster a sense of community and encourage more women to have exposure in their roles in technology. I think it’s essential to highlight and celebrate the achievements of women in the industry and to empower them to take a seat at whatever table they want to.

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