Inside SwellSpace: Greg Monn, Co-Founder & CTO

In this special edition of Inside SwellSpace, we’re featuring one of the visionaries behind the platform. As Co-Founder and Chief Technology Officer of 3Together, Greg Monn has played a key role in shaping SwellSpace from the ground up.

With nearly three decades of software experience and a deep background in benefits technology, Greg brings thoughtful leadership, technical creativity, and a hands-on approach to everything he builds. From embracing a remote-first culture to modernizing the way benefits information is delivered, Greg’s work reflects both innovation and purpose. We sat down with him to learn more about his journey, what excites him most in the industry, and why the sound of a jet engine still brings back great memories.

Tell us a little about yourself. What drew you to join the SwellSpace team?
Greg: I’m Greg Monn, Co-Founder and CTO at 3Together. I’ve been working in software for 27 years and got my start in benefits tech when Shawn Jenkins hired me as the second engineer at Benefitfocus. I worked with Shawn for nearly 18 years and with Jessica Brewer for six to seven years, so teaming up with them again was a big draw.

Another factor was the remote nature of the company. I’ve worked remotely for most of my career. First from Greenville, while others were in Charleston, and then across distributed teams. SwellSpace was designed to be remote from day one, which felt like a natural fit.

What excited me was the shift away from transactional systems. For years, we helped employees enroll in benefits and helped HR teams manage payments and processes. But SwellSpace gives us the opportunity to focus on communication, helping people understand their benefits, not just sign up for them. I was also excited to build in a new way using pure APIs and distributed architecture, instead of relying on older models like EDI or monolithic systems.

What’s your role at SwellSpace, and what does a typical day look like?
Greg: I’m the Chief Technology Officer, and I also serve as Chief Compliance Officer. My day involves a little bit of everything. I support the sales team with technical help and demos, assist the marketing and implementation teams with documentation and setup guidance, and manage our remote development team.

I still get to write code every day, which is something I truly enjoy. Sometimes it's small tweaks or bug fixes, and other times it's building new features or improving existing ones. I also interact with clients and prospects, which is always rewarding. It’s powerful to watch someone use our application to bring their benefits content to life and help employees understand what they have access to.

What’s something interesting you’re seeing in the HR, benefits, or software space right now?
Greg: There are a few things I find fascinating.

One is how frequently benefits and regulations continue to evolve, especially those coming from government and financial institutions. Another is the growing range of insurance options now available to employees.

I’ve also been struck by how involved brokers are in supporting their employer groups. Their dedication to bringing timely, helpful information to clients and elevating service is something I really admire. It’s clear they care deeply about helping employees make informed decisions.

What’s your favorite part of working at SwellSpace?
Greg: For me, it’s the flexibility and work-life balance. Being remote gives me the freedom to work from wherever I need to be, and I also value having a home base in Charleston where the team can come together in person.

I start my days early so I can wrap up in time to spend the evenings with my family, which means a lot, especially while working in a startup environment. I also love what we’ve built. SwellSpace is always on and accessible, whether someone is using a desktop, mobile device, or tablet. Whether it’s an employee, dependent, HR leader, or candidate, we’ve created a way for them to easily find what they need when they need it.

Just for fun, what’s your favorite movie, and what do you love about it?
Greg: I’ve always loved the Top Gun movies, the original and Maverick. A close second would be the Point Break films, both the original and the remake. Top Gun was one of the first movies I remember seeing in a theater. I was on a swim meet trip with my sister, and a group of us went together. I was instantly fascinated by the airplanes and how they were flown.

For about 12 years, my family would vacation in Pensacola Beach over the Fourth of July. One of the highlights was watching the Blue Angels perform at their home base. It was incredible to see them fly in formation: powerful, precise, and completely captivating. Those memories have stayed with me.

Want to connect with Greg?
If you're curious about the technology behind SwellSpace or how we’re creating a more accessible, modern approach to benefits communication, Greg is always open to a conversation. Whether you're a broker, employer, or fellow builder in the benefits space, feel free to reach out and learn more about the work we’re doing at SwellSpace.