The Story of Thoughtful AI: Building the Future of Healthcare Administration

Sometimes the biggest opportunities come from seeing what others overlook. In a recent Category Visionaries episode, Alex Zekoff, CEO of Thoughtful AI, shared how a $7 trillion insight led to reimagining healthcare administration.

The story begins in 2017 at Deloitte, where Alex was implementing RPA (Robotic Process Automation) solutions. “I really had the insight that if you fundamentally market size how many people on annual basis operate software, it’s $7 trillion of labor, move data around,” Alex recalls. This observation sparked a vision: if this work would eventually be automated, someone needed to build the solution.

But timing is everything. “I hit this fork in the road post MBA. I was 32 at the time,” Alex shares. The conventional path was clear: continue climbing the consulting ladder, aim for partner by 40. Instead, he chose risk. “I said, this is the time in my career to take risk. I have no kids… really, no liabilities. And so I said, let’s jump off here.”

January 2020: Armed with $40,000 from friends and family, including his co-founder as first angel investor, Alex launched what would become Thoughtful AI. Two months later, COVID hit. “It was like the universe was just handing me everything once in a platter,” Alex remembers. With just one pilot customer and limited runway, the stakes couldn’t have been higher.

But rather than spell disaster, the pandemic validated their approach. Their first customer, despite the uncertainty, remained committed. “We deployed our MVP of our platform plus the product in six weeks. Remote got to a first sort of pilot revenue. It was $2,000 a month,” Alex shares. This early validation proved crucial.

The next two years brought experimentation across multiple industries. By 2022, they had 85 robots deployed across 35 customers. But data analysis revealed something surprising: their healthcare implementations were delivering extraordinary results, with 1000% ROIs and 200% net revenue retention.

This discovery led to a pivotal decision: focus exclusively on healthcare. Coming from outside the industry proved advantageous. “I love it because I have no preconceived notions in healthcare of how it’s supposed to be done,” Alex explains. This fresh perspective helped them reimagine how automation could be delivered.

Today, Thoughtful AI takes a unique approach to implementing AI solutions in healthcare. Rather than selling separate components, they provide a complete package: “We are your internal team, we are your implementer, and we are your technology.” This simplified model, combined with outcome-based pricing, has resonated strongly with healthcare providers.

Looking ahead, Alex sees Thoughtful AI playing a crucial role in healthcare’s future. “We believe getting to 100 million ARR, 100 customers, we can achieve that by 2026,” he states. But their ambitions extend beyond these numbers. “We do believe after a blockbuster, we might IPO with healthcare. But after that, we do have ambitions to go into government in Fortune 500 as different categories where we could play with our platform.”

The company is also positioning itself for the next wave of AI innovation. “We actually believe all the data, the metadata we’re collecting on processes will create really innovative large process models that are going to be really interesting to sell as a new product and service in five to six years,” Alex reveals.

For founders weighing their own entrepreneurial leap, Alex’s journey offers a powerful reminder: sometimes the best time to take a risk is when conventional wisdom suggests playing it safe. As he puts it: “If I spend six to eight years grinding on something I love and it doesn’t work, I had conviction that those skills would be useful in the market, and at least I went for it.”