VRWS Leadership Interview of the Day

1. What inspired you to enter the vacation rental industry?

Completely accidental. I had an investment property which became vacant during 2008 recession and it was difficult to find a tenant. A prospect asked me if I furnish the property he’s willing to rent it for 6 months. I agreed, and 6 months after he left I was left with a fully furnished unit. Airbnb was just making news and I put up the property. I discovered the yield was much better than long term.

Armed with this information, I started doing lease arbitrage and scaled to 200+ properties. With scale came many challenges: seamless self checkin, Guest & Payment verification, security deposit collection. Given there was no solution in the industry, I put my Software Engineering skills to work and built a solution to solve this pain point.

Back in 2019, I’d already spent nearly a decade scaling a short-term rental business to over 200 properties. But no matter how much we grew, one thing kept dragging us down: guest service requests.

You know the kind—

“Can I check in early at 2pm?”

That single question would trigger a 20-message chain across our ops manager, housekeeping team, inspectors, and guest services. Even then, we still had to send a payment link, wait for the guest to pay, manually update the reservation in the PMS, and then update the smart lock to activate at the right time.

Now imagine doing that 15 times a day. It was a total time suck.

So, we built a workflow to automate it all—no human involvement, just “set it and forget it.” Within hours of launching it, I got an email:

“Ela S. has purchased 2pm early check-in for $39.”

That moment was electric. It felt smoother than a $3,900 payout because it meant we’d just freed up 10+ hours of repetitive tasks—without lifting a finger.

By the next day, we’d generated nearly $600 from upsells. Today, ChargeAutomation users generate over $5 million in upsell revenue annually, all fully automated.

That pain point—and the magic of solving it—is what inspired me to help others in the industry do the same.

2. What sets your company apart in the vacation rental industry, and how do you ensure you stay ahead of the competition?

At ChargeAutomation, we don’t just automate guest flows, we eliminate friction.

Most platforms either focus on guest experience or backend operations. We bridge both, creating a seamless end-to-end journey that benefits guests and property managers. From ID verification, deposits, and upsells to payments and check-in, everything is fully automated, deeply integrated, and customisable to each operator’s needs.

What truly sets us apart is this: we’re operators first, tech builders second. Our roots are in running hundreds of short-term rentals, so we understand the chaos behind the scenes. That gives us a sixth sense for the real pain points, the ones that often go unnoticed by pure tech companies.

To stay ahead, we focus on three things:

1. We ship fast and adapt faster. When regulations change or guest expectations shift, we’re already building the solution.
2. Our platform isn’t one-size-fits-all. Operators can tailor workflows to match how they run their business.
3. We integrate with 100+ PMS and payment gateways globally, giving users more options, more reach, and more control.

Our mission is simple. Help operators grow revenue and reclaim their time, without adding overhead. That focus keeps us sharp, relevant, and ahead of the curve.

3. If you attended the 2024 Vacation Rental World Summit in Porto, what was the most exciting or valuable takeaway for you? And looking ahead to the 2025 edition in Rome, what are you hoping to gain or experience this time?

We didn’t make it to the 2024 edition in Porto, but we definitely felt the energy from afar. The community buzz, innovation shared onstage, and the quality of connections people made left us with a serious case of FOMO.

That’s exactly why we’re excited to be in Rome this year.

For 2025, I’m hoping to connect more deeply with fellow operators and tech partners. Not just to show what ChargeAutomation can do, but to listen and learn what challenges are keeping people up at night. The industry’s evolving fast, and these events are goldmines for insight, collaboration, and shaping what comes next.

Plus, let’s be honest… you can’t beat Rome as a backdrop for big ideas.

4. Beyond business, what’s one experience or destination that left a lasting impression on you, and why?

Going back to Eritrea left a deep and lasting impression on me. It’s where I’m from, but every time I return, I see it with new eyes. The blend of culture, history, and resilience in the people is something you can’t really put into words. It has to be felt.

Walking through the streets of Asmara, with its unique Italian-modernist architecture and strong community spirit, reminds me how powerful simplicity can be. There’s a rhythm to life there that’s slower, more intentional, and it always helps me reset and reflect on what truly matters.

It’s the kind of place that grounds you, humbles you, and inspires you to build with more purpose.

5. What’s one fun fact, hidden talent, or little-known secret about you that other attendees should know to spark a great conversation with you?

Most people know me for tech and automation, but here’s something different.  I’ve been an equestrian since I was a kid. Horses were a huge part of my childhood, and I’ve continued riding ever since.

It’s more than just a hobby. It’s where I learned focus, patience, and how to read non-verbal cues. Funny enough, those same skills come in handy when leading teams and building thoughtful technology.

So if you’re into horses, outdoor adventures, or just want a break from tech talk, come say hi.