Q: You started your career as an auditor and tax consultant at Ernst & Young, then led finance teams at companies like Verizon, Fleetmatics, and PeopleFluent. What drew you to finance, and how did those early roles shape the way you lead today?
GN: I actually started as a math major at Holy Cross. I took an accounting class junior year and loved the logic of it. I joined Ernst & Young while completing an accelerated MBA at Boston University, earned my CPA, and later pursued a master’s in taxation at Suffolk.

Audit taught me to ask questions and verify the details; leading finance teams taught me to understand the business behind the numbers. Today, I still lead with both perspectives be curious, know your facts, and never lose sight of the people doing the work.

Q: After more than 20 years leading finance teams at large private and public companies, what made you decide to found Rapid Cloud Partners, and what was the hardest part of making that leap?
GN: At Fleetmatics, I helped lead a major ERP transformation and saw firsthand what a difference the right cloud technology could make for a business. I had spent more than 20 years in corporate finance, and that experience gave me a unique perspective on how technology could solve real business challenges. After Fleetmatics was acquired by Verizon, I realized how much I missed the flexibility, independence, and entrepreneurial energy of a smaller organization.

When the opportunity came to start my own consulting firm, I knew I wanted to focus on NetSuite and Salesforce, two platforms I believed could make a tremendous impact on how companies operate. That’s what led me to found Rapid Cloud Partners in 2019.

The hardest part was trading a familiar corporate career for the uncertainty of building something from scratch and, more importantly, believing in myself enough to do it. I had spent my career working for established companies, surrounded by talented teams and resources. Suddenly, I had to trust that I could build something successful on my own. But I also knew what clients needed because I had sat in their chair. I understood their challenges, their frustrations, and what they expected from a consulting partner. Looking back, I had the experience, the relationships, and the knowledge. What I needed was the confidence to bet on myself. Taking that leap was one of the most intimidating decisions I’ve made, but also one of the most rewarding.

Q: Finance and accounting leadership, and the technology world you now work in, have historically been male dominated. What challenges did you face as a woman moving up through those fields, and what helped you keep advancing?
GN: Early in my career, finance and accounting were very male-dominated fields, particularly at the executive level. There weren’t always many women in the room, and I learned that being good at your job wasn’t necessarily enough. You had to be willing to speak up, trust your judgment, and have the confidence to take on opportunities, even when you weren’t entirely sure you were ready.

One of the people who had the greatest impact on my career was Steve Lifshatz, a former CFO, longtime mentor, and someone I still keep in touch with today. Steve believed in me and my abilities, sometimes more than I believed in myself. I remember him calling me when he was preparing to take Fleetmatics public and saying, “Gayle, I need your help.” I was comfortable in my role at the time, but he saw something in me and encouraged me to take on a much bigger challenge. That opportunity became one of the defining experiences of my career.

I think there’s an important lesson in that experience, particularly for women. Sometimes it takes someone else recognizing your potential to help you recognize it yourself. Steve happened to be a man, and I think that’s worth emphasizing. Advancing women in leadership isn’t just about women supporting women. It’s about having leaders, regardless of gender, who recognize talent, open doors, and give people the confidence and opportunity to succeed.

What helped me continue advancing was learning to believe in my own abilities and becoming more comfortable taking risks. I didn’t always have all the answers, but I knew I could figure things out. That confidence eventually helped me make the biggest leap of my career: leaving corporate finance to start Rapid Cloud Partners.

Today, I try to carry those lessons into my own leadership. I believe in giving people opportunities to stretch beyond what they think they’re capable of, supporting them along the way, and making sure they know their contributions matter. You can have high expectations, hold people accountable, and still lead with encouragement, warmth, and a sense of humor. Sometimes the most powerful thing a leader can do is believe in someone before they fully believe in themselves.

Q: Your personal motto is “Trust but verify.” How has that guided your career decisions and your leadership style, and how does it show up in the way RCP serves its clients?
GN: It’s not about distrusting people. It’s about respecting the stakes.

In finance, a number can look right until you understand where it came from. The same is true with technology. At Rapid Cloud Partners, we listen to what clients tell us, then look closely at their processes, data, and systems before recommending a solution.

I trust talented people to do their jobs, but I believe good leaders ask questions, validate assumptions, and follow through.

Q: You’ve helped companies use cloud-based tools to streamline operations. What advice would you give women who want to move from corporate finance into entrepreneurship or into leading in tech, and what do you wish you’d known when you started?
GN: Don’t underestimate how transferable your experience is. I spent more than 20 years in corporate finance before starting Rapid Cloud Partners, and I quickly realized that understanding how businesses operate and the challenges they face was one of my greatest strengths. I wasn’t a technologist by trade, but I understood the problems technology needed to solve because I’d experienced them firsthand.

One of the biggest lessons I’ve learned is that being great at what you do is only part of the equation. 

You can have all the expertise in the world, but if you’re starting a business, you need clients. That means putting yourself out there, building relationships, networking, and getting comfortable selling yourself and what you have to offer. Opportunities don’t always come knocking. Sometimes you have to create them.

I’ve also been fortunate to work alongside incredibly talented women throughout my career who have reinforced the importance of surrounding yourself with people who bring different strengths and perspectives. You don’t have to know everything or do everything yourself. Build a network of people who support, challenge, and inspire you.

What I wish I’d known earlier is that you don’t need to have all the answers before getting started. Trust your experience, believe in what you bring to the table, and don’t be afraid to take that leap. Sometimes the hardest part is simply having the confidence to bet on yourself.

Q: What is one word of advice you can offer to young women who want to reach your level of success?
GN: Confidence. Not because you know everything, but because you can figure things out.

Q: Can you tell our audience one of your most memorable moments of your career?
GN: One of the most memorable moments of my career was helping take Fleetmatics public in 2012. I was recruited by a former CFO who believed in me and asked me to help prepare the company for its IPO. It was an incredible opportunity, but also a tremendous challenge. We had to strengthen our financial operations, clean up our accounting processes, and prepare the business for the scrutiny that comes with being publicly traded. Seeing all that hard work come together when we successfully went public was an unforgettable experience.

What makes that chapter of my career even more meaningful is that it ultimately changed the direction of my professional life. Our work implementing and optimizing NetSuite opened my eyes to the impact technology could have on a business. I enjoyed that transformation so much that it eventually inspired me to leave corporate finance and start Rapid Cloud Partners. Looking back, it’s amazing how one opportunity can completely change the course of your career.

Q: At the start of your career, what do you wish you had known?
GN: Careers are rarely straight lines. An accounting elective changed mine, and a technology implementation eventually led me to entrepreneurship. Stay open to the unexpected.

Q: What advice would you give to young women who want to pursue their dream and start a business?
GN: Start with something you know well and a real customer need. You can learn the rest as you go, but you need to believe in the problem you’re solving. Don’t underestimate the importance of building relationships, networking, and putting yourself out there. You can be incredibly talented at what you do, but you still need to find customers and convince them to believe in you. Surround yourself with people who complement your strengths, and don’t wait until you feel completely ready. Sometimes you just have to take that leap and trust yourself to figure things out along the way.

Q: What advice would you give to young women who want to succeed in the workplace?
GN: Do excellent work, build relationships, and make your contributions visible. Ask questions, speak up, and don’t assume someone else will advocate for you. I’ve been fortunate to have mentors who believed in me and encouraged me to take on opportunities I might not have pursued on my own. Find those people, learn from them, and be willing to step outside your comfort zone. Confidence comes with experience, but you also have to be willing to take chances before you feel entirely confident. And as you advance in your career, remember to extend those same opportunities and encouragement to others.

Q: Can you tell us how you manage your work-life balance?
GN: I think work-life balance is less about having a perfect schedule and more about being flexible and knowing your priorities. As a business owner, there are times when that means pulling out my laptop in the evening, early in the morning, or from wherever I happen to be. I work hard, and I genuinely love what I do, so the lines between work and personal life aren’t always clearly defined.

But I’ve also learned that flexibility works both ways. Just as I’m willing to adjust my personal schedule when the business needs me, I need to give myself permission to step away when something important in my personal life needs my attention. That means setting boundaries, making time for the people and things that matter most, and recognizing when I need a break. Balance isn’t about giving everything equal time every day. It’s about knowing what deserves your attention in the moment and being intentional about where you spend your energy.

Five Things About Gayle Nelson

1. What celebrity would you like to meet at Starbucks for a cup of coffee?
Martha Stewart. I’ve always admired women who build successful businesses by turning their passions and expertise into something much bigger.

2. What’s your favorite thing to do in your free time?
Golf. I enjoy the game and the chance to spend time with people outside the office.

3. What’s your favorite quote or saying?
“Trust but verify.” It has served me well in business and in life.

4. Do you read reviews, or just go with your gut?
A little of both. I trust my instincts, but I like to do my homework. See my motto!

5. What was your favorite subject in school?
Math. I loved solving equations, which probably explains why accounting clicked for me.