Today we’d like to introduce you to Rob Henry.
Hi Rob, thanks for joining us today. We’d love for you to start by introducing yourself.
My story starts on a football field. I was a two-time team captain and starting quarterback at Purdue University, and after college I signed with the Oakland (now Las Vegas) Raiders as a free agent. Football had been my entire world for 25 years — and then, almost overnight, it wasn’t.
That transition was harder than most people realize. While my peers had been building careers and figuring out their paths since high school, I was 25 with no real plan and very little experience outside of athletics. It was humbling. I spent a couple of years working with a friend and rehabbing football injuries, then took a sales job, and eventually found my way into real estate — where I’ve been building ever since.
The discipline and work ethic from football absolutely carried over, but the bigger lesson was learning how to constantly adapt. Starting over in a new field at 25 forces a kind of adaptability that I think has served me well as an entrepreneur.
That entrepreneurial path eventually led me to co-found SouthDesk with my wife. She was born and raised in South America, and we wanted to build something that created opportunity on both sides of our worlds. SouthDesk connects US businesses with top-tier Latin American talent, and we’ve grown to serve clients from small businesses to large multinational companies — with team members spread throughout Latin America.
Today I split my time between commercial real estate and growing SouthDesk. Both businesses are built on the same foundation: hard work, relationships, and a genuine desire to deliver results for the people we work with.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Definitely not smooth. The first major challenge was the transition out of football itself — identity. When you’ve been an athlete your whole life, losing that identity is disorienting in ways that are hard to explain. I didn’t know who I was outside of the game.
Breaking into real estate without a network or business background was its own uphill climb. There’s no playbook handed to you — you figure it out through a lot of trial and error, rejection, and learning from people further down the road than you.
With SouthDesk, the challenge has been building something from scratch across multiple countries, multiple cultures, and multiple legal systems. Navigating labor laws, building trust with US clients, and scaling a team that operates remotely across Latin America — none of that comes easy. We have some really ambitious revenue goals over the next few years and a lot of challenges between here and there to achieve those goals all while continuing to build a culture and company our team members and clients are proud to be associated with.
But honestly, the hardest thing has been the mental discipline to keep going when results are slow. Football taught me that, but business tests it in a different way — there’s no offseason, no game clock, and no coach telling you what to do next.
We’ve been impressed with SouthDesk, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
SouthDesk is a nearshore staffing and business process outsourcing firm that connects US companies with the top 1% of Latin American professionals. We serve businesses of all sizes — from solopreneurs to large multinational corporations — placing professionals across virtually every function: accounting, marketing, operations, HR, construction, real estate, technology, and more.
What sets us apart is the quality of our talent and the depth of our service. We’re not just a recruiting agency — we offer end-to-end solutions including employer of record, payroll, HR management, benefits, account management, and dedicated support. Our team members are spread throughout Latin America, giving us access to a deep and diverse talent pool.
What I’m most proud of is the culture we’ve built on both sides of the relationship — our team gets access to meaningful, well-paying work with US companies, unmatched benefits and profit sharing, while our clients have the opportunity to expand their businesses by hiring reliable, high-performing professionals who become long-term assets to their companies. We’re creating real economic opportunity while solving real problems for US businesses.
What’s next?
The primary focus right now is scaling SouthDesk. We have aggressive growth goals over the next few years and a clear roadmap to get there — expanding our client base, deepening our service offerings, and continuing to build the infrastructure and culture that makes SouthDesk a place both clients and team members want to be long-term. We’re also actively building out our AI and RPA capabilities so our clients can stay ahead of their competitors and continue to operate at the highest level.
On the real estate side, I’m always looking for the next opportunity. The Florida market continues to evolve and there’s no shortage of interesting deals to pursue. Beyond that, there are other ventures I’m entertaining and exploring — I’ve never been someone who believes in limiting my potential.
But beyond business, I’m focused on what matters most — my faith, my family, and continuing to grow as a husband, father, and person. Those things are the foundation everything else is built on.
Pricing:
- southdesk.net/pricing
Contact Info:
- Website: https://southdesk.net
- Instagram: https://www.instagram.com/southdesk/
- Facebook: https://www.facebook.com/SouthDesk/
- LinkedIn: https://www.linkedin.com/company/southdesk
- Twitter: https://x.com/southdesk
- Youtube: https://www.youtube.com/@SouthDesk
