Penn Gaines, CEO and Co-Founder of Payfluence, is Taking the Hard Work Out of Managing the Workplace

We sat down with Payfluence CEO Penn Gaines to discuss startup life, learning how to think, and how the secret to success might just lie in team culture.

This blog post is part of our “Shop Talk” founder series, which celebrates Word of Web clients as we dive into what drives them and how they embrace the entrepreneurial spirit.


Tell us about Payfluence. What’s your elevator pitch?

Payfluence is an all-in-one human capital management software. We’re B2B focused and work with companies that typically have 50-500 employees. Our technology allows businesses of all sizes to offer a better employee experience, starting even before a candidate comes onboard. We help manage every aspect of the workplace, from hiring and development to payroll and culture.

What sparked the idea behind your company? How did it come to fruition?

My partners and I liked the idea of a business model that offered recurring revenue. We knew we wanted to compete against big companies and started looking at payroll, or what’s now known as HCM. We discovered that a lot of the big companies offered strong technology, but lacked the human element. The companies that had a strong personal touch lacked the right technology. So, we set out to bridge that gap and create a company that’s rooted in agile tech, but is also backed by excellent customer support.

What unique gap does Payfluence fill?

In addition to our hybrid of strong technology and great service, we do the little things very well. We answer the phone in 3 rings and reply to emails within 4 hours. That’s really important to customers and sets us apart. Our software platform is also fantastic — we can go toe-to-toe with any company and our tech is equal or better!

Payfluence CEO and Founder Penn Gaines


What are the most challenging and most rewarding parts of what you do?

To me, the most challenging and most rewarding part is one in the same — it’s starting at zero. When you start a company, it’s like a game. There’s a race to profitability, but you have to do it the right way. I always say that creating a startup is like having the best neighbors. It’s the people you live side by side with — you’re all on one team. There’s a great sense of accomplishment because you see what you’re building together every day.

Where would you like to see your business in 5 years?

We’re not focused on hyper-growth, but rather taking one smart step at a time. Of course, we’d like to seize opportunities while continuing to grow and serve the market. But, we want to bring on clients and have them become our brand advocates. We want to grow in a grassroots kind of way, all throughout the Southeast region.

What’s the best advice and worst advice you’ve ever gotten?

The best advice I’ve gotten is that investing in yourself is the best investment you’ll ever make. You can’t exchange time for money, so find something that fulfills you. When you invest in yourself, you’ll do all you possibly can to make it work.

The worst advice is something we’ve all probably heard. Do good in school, then go get a good job working for someone. I think you should go to school to learn to think — then go start something yourself!

Payfluence team working


What is the biggest lesson you’ve learned since starting your own business?

The biggest lesson I’ve learned is the importance of being agile. Even with 14 years of experience, I had to reassess my approach. I thought the doors would swing wide open and we’d go right into the target market. But, you have to constantly re-think what you thought you knew.

What advice do you have for other entrepreneurs and CEOs just starting out?

Find really strong mentors and partners who have been in your shoes. There’s no magical formula, but if you surround yourself with good people, it helps tremendously.

What about your work are you most proud of?

I’m most proud of the team and culture we’ve built. If you have great people, you’ll never get stuck. You’ll overcome adversity and excel. If you have a strong culture, people won’t quit when challenges arise. We’re very team focused here at Payfluence and that makes me really proud.

Ready to see Payfluence in action? Visit their website and request your free demo here. Be sure to follow them on LinkedIn to keep up with their inspiring journey.

The Payfluence team values a fun culture



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