At Get Covered, many of our strongest ideas come from people who have experienced the challenges our customers face firsthand. Stephanie Simpson, our Go-to-Market Manager, brings exactly that perspective.
Before joining the team, Stephanie led portfolio-wide go-to-market strategy at Progress Residential, supporting 100,000 homes across 26 markets. Today, she uses that operator experience to help Get Covered develop and deliver solutions that reduce friction, strengthen operations, and create meaningful value for property management teams.
We sat down with Stephanie to learn more about her path to Get Covered, her approach to collaboration, and what she believes the property management industry needs most right now.
How did your career path lead you to Get Covered?
Before joining Get Covered, I worked at Progress Residential, where I led go-to-market strategy across a portfolio of 100,000 homes in 26 markets. My work focused heavily on resident products and services, so I was constantly thinking about how to improve the resident experience, reduce operational friction, and create scalable revenue opportunities.
One of the first major projects I inherited was turning around a renters insurance program that was, honestly, very broken. That process led me to Get Covered. After months of due diligence, plenty of questions, and Brandon and Ryan ultimately winning us over, I led the transition of the entire Progress portfolio to Get Covered.
The results were significant. Within the first four months after launch, we saw a 29% increase in active policies and introduced a completely new revenue stream for the business.
More importantly, I saw firsthand what a strong partner Get Covered could be. I believed in the product, the people, and the impact the company could have because I had experienced it from the operator side.
Joining Get Covered felt like a natural next step. I came here with a real customer perspective, a passion for solving these problems, and a genuine belief in what we are building.
How do you balance strategy, execution, and cross-functional collaboration?
I try to start with the big picture and then bring it down to what actually needs to happen next. Strategy is important, but only when it translates into clear actions, ownership, and measurable results.
Cross-functional collaboration is a major part of that process. I believe the best solutions come from getting the right people in the room, asking thoughtful questions, listening closely, and connecting the dots across teams.
My approach is usually to clarify the goal, identify the gaps, align the stakeholders, and keep things moving.
As a busy mom of two, I’ve also learned the art of prioritization. Not everything can be the fire of the day, even when it feels like it. I try to focus on what matters most, keep everyone aligned, and bring plenty of energy, excitement, and a little cheerleading along the way. G-O Team!
What is one challenge property management teams are facing that deserves more attention?
One of the biggest challenges property management teams are facing right now is capacity. Teams are stretched thin and being asked to do more with less, all while improving the resident experience, protecting NOI, and managing increasing operational complexity.
The industry has to become more serious about adopting solutions that are true no-brainers, tools that reduce friction, save time and energy, generate revenue, and lower costs.
When a process is still highly manual, repetitive, or dependent on onsite teams chasing down information, there is probably a better way to manage it.
Technology and AI are no longer nice-to-haves. They are becoming operational necessities. The companies that embrace smarter automation, stronger workflows, and more proactive technology will be the ones that create real leverage for their teams.
That is also what sets Get Covered apart. We are not simply an insurance vendor. We are a technology company building solutions around the problems property management teams are facing today while anticipating what they will need next.
Property management companies do not want another vendor. They want a partner who understands their pain points, reduces the burden on their teams, and helps move the business forward.
Outside of work, what activities or hobbies help you recharge?
Most of my life outside of work is centered around my family. I’m a mom of two, and my kids keep life very full, fun, and slightly chaotic…in the best possible way.
Whether we’re at soccer, playing outside, traveling, or simply enjoying everyday family life, that is where I feel the most grounded.
I also enjoy anything that gives me a little creativity or a chance to reset: good coffee, being outside, planning a fun trip, Pilates when I can, and spending time with the people I love. I’m someone who gets a lot of energy from connection, laughter, and meaningful conversations.
And honestly, sometimes recharging looks like eating chocolate and binge-watching trash TV after the kids are asleep, which any parent knows can feel like a luxury vacation.
Bringing the Operator Perspective to Get Covered
Stephanie’s firsthand understanding of property management operations helps ensure that Get Covered’s go-to-market strategy remains closely connected to the needs of the teams we serve.
Her ability to combine big-picture thinking with practical execution, and bring plenty of enthusiasm to the process, makes her an invaluable part of the Get Covered team.
We’re excited to have Stephanie helping us build smarter, more scalable solutions for the future of property management.
