SheTech Interns Interview Ashlee Cowley
Ashlee Cowley, Global Services Head at Entrata, shares insights on leadership, AI, motivation, and balancing career ambition with personal priorities—all while staying true to her values and vision.
People & Culture
Ashlee Cowley: Leading with Intention, Balancing with Heart
As the head of global professional services at Entrata, Ashlee Cowley leads a team of over 200 people who help apartment companies implement ERP (Enterprise Resource Planning) software. Her team focuses on three main goals: putting the right people in the right roles, creating strong processes, and using performance metrics to constantly improve. Their mission is simple—make it easy for clients to manage everything from accounting to resident applications using Entrata’s platform.
Solving Problems with Purpose
When problems pop up, Cowley doesn’t waste time. “I handle conflict very much head-on,” she says. Whether it’s a small issue or something bigger, her process starts with understanding the root cause. From there, she creates a plan to solve it. Once the issue is resolved, she reflects on what happened to help prevent it from happening again. It’s a thoughtful, no-nonsense approach that shows her commitment to building a strong, resilient team.
The Realities of Work-Life Balance
In a world where work is always “on” thanks to emails and messages, Cowley admits that balancing work and life isn’t easy. “Work never really shuts off for me due to the constant influx of digital communication,” she says. But even in the chaos, she emphasizes how important it is to set boundaries and prioritize the moments that matter most.
“It’s a constant juggling act,” she admits. “But I try to shut work off during important life events. That’s where discipline comes in.” For Cowley, work-life balance doesn’t mean perfect separation—it means making intentional choices.
What AI Means for the Future
The future of technology services is changing fast—and Cowley is excited. “It’s gonna be super exciting to see what comes from [AI],” she says. Right now, her team is examining every process they use and asking questions: Is this manual? Is it inefficient? Could AI automate it?
The goal isn’t to replace people—it’s to free them up to focus on high-impact work. “Over time, we may see a reduced workforce,” she explains, “but the people who remain will be high-caliber talent working on really important things.”
The Power of Education
Cowley studied Economics at the University of Utah, with a minor in Business. That education continues to influence her work. “The general business principles I learned in school have helped me in this role,” she says. Looking back, those were the classes that stuck with her most.
Her advice? “Have at least a little bit of business knowledge. You never know when you’ll need it.”
What Keeps Her Motivated
Cowley finds motivation in three key areas. First, it’s the people. “One of the big things that keeps me motivated is the people I work with,” she says. “I have an amazing team.”
Second, it’s the work itself. Cowley loves leading her department and owning the results. “I have the autonomy to run my department, to make changes, and see what works. Seeing results—positive or negative—keeps me motivated.”
And third, it’s her family. “Being able to provide for your family is important,” she shares. “We love to go on cruises—we do a couple every year. Being able to go on those fun trips is also very motivating.”
The Toughest Part of Leadership
Leadership comes with tough choices—especially when it comes to people. “Letting someone go is one of the hardest parts,” Cowley says. “You get the privilege of hiring, mentoring, and developing people, but sometimes it’s just not a good fit anymore.”
She admits it doesn’t get easier, especially after working with someone for years. But integrity, honesty, and transparency are her core values—and she sticks to them, even when it’s hard.
Advice for the Next Generation
For young people thinking about their futures, Cowley offers this advice: “Find a company with a good mission and culture. There’s no amount of money anyone could pay me to sacrifice those beliefs.”
She also encourages diving in fully: “Invest yourself into the company you join. Learn everything you can—it’ll help you wherever you go next.”
Looking Ahead
As Cowley reflects on the future, she’s thinking more about balance. “Do I want more? Or am I comfortable with where I am?” she asks. Right now, she’s passionate about her work—but she also wants to enjoy more of life outside of work.
“I want to be a CEO someday,” she says. “I’m really passionate about operations.” But she also dreams of traveling the world with her family, especially while her son is still young. “So, the answer is… I’ll let you know when the time comes.”
Redefining Success
For Cowley, success isn’t just about titles or promotions. It’s about finding happiness and being present with the people who matter most. “It’s about comfort, time with family, and feeling good about the work you do,” she says.
Ashlee Cowley proves that leadership doesn’t have to look one way. It can be bold, thoughtful, balanced—and maybe even a little adventurous.
SheTech Media Interns, Siya Jain and Rumaana Patel, attend Cedar Valley High School in Eagle Mountain, Utah. They actively participate in SheTech programs, including the SheTech-TechBuzz Media Internship for which they interview and write about Women Tech Awardees. Their work is published on TechBuzz News, Silicon Slopes, and other media channels.
Siya wants become a successful entrepreneur. Always seeking opportunities to expand her knowledge of business, Siya is committed to building her entrepreneurial skills through hands-on experiences such as networking, writing, and education. She serves as the SheTech president of her school. She is also a student board member.
Rumaana is similarly passionate about technology and dreams of launching her own business. She is working toward a career in software engineering, taking advanced programming courses to strengthen her skills. Outside of coding, she has been dancing for eight years, a pursuit that fosters both discipline and joy. She also enjoys sketching and reading, which fuel her creativity and curiosity.