Thoughtful AI is a company that is pioneering a new approach to automation for all healthcare providers. Pulse 2.0 interviewed Thoughtful AI co-founder and CEO Alex Zekoff to learn more about the company.
Alex Zekoff’s Background
What is Alex Zekoff’s background? Zekoff said:
“I started my career in technical consulting for large aerospace companies around 2009. I then moved to Japan for a couple of years to help Mitsubishi set up a company. After that, I was sponsored to attend the Haas School of Business at the University of California, Berkeley, where I focused on entrepreneurship, design thinking, and venture capital.”
“Post-MBA, I returned to aerospace and began working on AI-enabling technologies such as robotic process automation, machine learning, optical character recognition, and natural language processing. It was there that the genesis of Thoughtful AI was born.”
“I knew there had to be a better use for current tech, so in 2019, I made a move. By January 2020, I started a company to democratize this technology through a pioneering model called AI-as-a-Service, or AI Agents. We began developing our tech that year and soon had our first proof of concept and initial customers. Since then, we’ve been scaling and innovating, specifically in healthcare revenue cycle management, tackling one of the largest and most consistent pain points in the industry and sector.”
“We’ve raised $40 million to date and are the fastest-growing healthcare agentic AI company in the world. Our focus is on building world-class technology for healthcare providers that don’t have access to Fortune 500 enterprise-grade tech.”
Responsibilities As CEO
What are your primary responsibilities as CEO? Zekoff shared:
“Everything, really. I particularly focus on sales as the chief revenue officer and maintaining world-class economics. With this new business model, I keep a close eye on unit economics to ensure profitability for every deal.”
“I also manage business operations, both in the U.S. and our offshore engineering teams. As the product platform owner, I steer the product vision for our engineering team. Additionally, I oversee branding and marketing, ensuring our brand projects a super-premium image. Our approach is “white glove premium,” so I ensure our brand aligns with how we sell our products and services.”
Formation Of Thoughtful AI
How did the idea for the company come together? Zekoff reflected:
“The idea started with the realization that people moving data on computers is pretty absurd. Fast forward 50 years, and photos of us typing and transferring data will seem as outdated as old telephone operators plugging in cords. By designing from a future standpoint, we aim to create a world where people aren’t stuck behind computers moving data. The goal is for computers, or AI self-learning systems, to handle complex workflows and add real value.”
“Right now, the tech business model is to sell productivity software to a human and then sell licenses for each user. If a company has 100 employees, you sell 100 licenses to HubSpot or some other app. In our model, we operate on top of these systems, mimicking the workflows that a person would follow in various systems.”
“This approach allows us to fully replace the person in these tasks, freeing them up for better work. Think of telephone operators: once automated, they moved into better, higher-paying jobs like customer and technical support, which doubled their pay within a decade. Our fundamental belief is that these repetitive jobs are holding people back from higher-paying and more needed jobs in today’s world.”
Favorite Memory
What has been your favorite memory working for the company so far? Zekoff replied:
“My favorite memories are when our customers text us, super delighted with the product experience, saying, ‘Hey, I’ve got a referral for you,’ or offering to be a reference for new customers. There’s no better feeling than building a product and service that genuinely adds measurable value in the world. Having customers come back and buy more and seeing our net revenue retention numbers soar, with the typical customer spending 220% of their initial purchase within the first year, is incredibly rewarding.”
Core Products
What are the company’s core products and features? Zekoff explained:
“Our platform helps us build our products, but we don’t sell the platform itself. It’s essentially AI building AI.”
“Our core products are our AI Agents, which are role-based and augment revenue cycle teams. We have EVA, our eligibility verification agent; CAM, our claims automation agent; PHIL, our payment posting agent; PAULA, our prior authorization agent; and DAN, our denials management agent.”
“These five agents make up the world’s first fully human-capable AI revenue management team. Together, they deliver incredible results, such as reducing the cost to collect to 3% or less, maintaining day sales outstanding under 30 days, and achieving clean claims rates of up to 99.5%, among other impressive metrics.”
Challenges Faced
What challenges have Zekoff and the team faced in building the company? Zekoff acknowledged:
“Overcoming industry challenges is a big part of our work. The healthcare industry is incredibly complex and often entrenched in outdated practices, with many providers still operating as if it were a decade ago.”
“For instance, many healthcare providers are still migrating to the cloud—something many companies did a decade ago. This means we often deal with providers that are not quite ready for our solutions, as their data isn’t centralized yet.”
“We overcome these challenges by offering white-glove service and tailoring our approach to each provider. Every provider is unique and requires a custom, strategic approach for deploying AI solutions effectively.”
“We are creating a category. We’re not selling productivity software. We’re selling the work. We’re selling the results, and so it’s a very different way to sell. We’re having to educate a lot of people on how this is the most efficient way to buy productivity, which is productivity itself.”
“We’re one of the earliest companies in this category called service as software, not to be confused with software as a service. We’re selling the service directly as a form of software and then managing, optimizing and training the agents. All of this is brand spanking new in the world, and so we have to create a lot of technology to make that magic happen.”
Evolution Of The Company’s Technology
How has the company’s technology evolved since the launch? Zekoff noted:
“We started by building AI Agents across various industries in the first couple of years to develop our platform and ensure we could deliver agentic AI. But in the last few years, we’ve focused solely on building integrations, templates and designs for revenue cycle management and healthcare admin processes. This shift to healthcare revenue cycle management for mid-market providers has allowed us to achieve exceptional outcomes by going extremely vertical in our approach.”
Significant Milestones
What have been some of the company’s most significant milestones? Zekoff cited:
“Fundraising milestones are a big one: seed, seed extension, and recently, Series A. Another exciting milestone is having around 30 providers live with our AI Agent solutions, delivering real value in production use cases.”
“I’m also thrilled that we’ve just reached our 30th U.S. employee mark. But what’s more impressive is our revenue relative to our headcount. We practice what we preach, using a lot of internal AI tooling. While other companies with similar revenue might have 80 or 90 employees, we operate with just 30 U.S. employees, staying extremely lean.”
“I’m proud that we’re building an AI-first company with top-tier talent. We have some of the best of the best, the 1% of the 1%, and I’m incredibly blessed to work with and learn from such talent every day. Our environment is very collegial, fostering great teamwork. So, our significant milestones span talent acquisition, customer success and capital growth.”
Customer Success Stories
When asking Zekoff about customer success stories, he highlighted:
“One that stands out is Cara Perry, the vice president of revenue cycle management at Signature Dental Partners, which has 98 practices across the U.S. About a year and a half ago, she started with their first AI Agent, which was a huge success. From there, they scaled to over 30 AI Agents, achieving incredible ROI. We love this story because we started with a proof of concept with Cara, and she sold our solution to her board. Now, we’re not only revolutionizing their revenue cycle management, we’re also expanding into other departments across the organization.”
Funding
When asking Zekoff about the company’s funding details, he revealed:
“We’ve raised $40 million to date. While I can’t comment on our valuation, I can say that even though we just raised a Series A, our revenue is strong enough that we could raise a Series B today based on that alone.”
“We’re very mature in our go-to-market strategy and continue to expand it, to continue achieving best-in-class go-to-market metrics.”
Total Addressable Market
What total addressable market size is the company pursuing? Zekoff assessed:
“The U.S. healthcare system’s back office and healthcare admin sector is about $1.5 trillion. Within that, total labor and people spending is significant. Our sweet spot, which is admin, is roughly $600- to $700-billion.”
“Focusing on mid-market, non-hospital segments, we’re targeting a $250- to $300 billion market in labor and tool spending for revenue cycle departments. It’s a massive market, and providers are constantly seeking help.”
“There’s also a looming job deficit in the next 10 to 15 years for revenue cycle roles as baby boomers retire, and Gen Z isn’t filling these data entry positions. Our AI Agents will become mission-critical in the near future.”
Differentiation From The Competition
What differentiates your company from its competition? Zekoff affirmed:
“We care. We really care. We really understand the pain points of the users.”
“We match our service and product to accommodate our buyer and our customer. That means we design, train, test and deploy AI Agents. We do everything.”
“Healthcare providers are already swamped. Topping their stack with another tool isn’t helpful. They need hands-on support, with people actively doing the work and being in the arena. One of our core values is ensuring our product and services are “in the arena” with our providers, so we practice what we preach.”
Future Company Goals
What are some of the company’s future goals? Zekoff concluded:
“We’re on a mission to fix the U.S. healthcare system. It’s a massive undertaking, and we believe it starts with getting providers paid.”
“If a provider makes $100 million but can only collect $70- to $90-million due to denied claims, that $10- to $30-million loss could have gone to practitioners, lowering bills and improving the patient experience. We all want to optimize for better health outcomes, not for providers to have to upcharge because 20% of their claims get denied. It all starts with the money. Securing all the funds enables providers to reinvest that capital into better health outcomes.”
“Our approach is rooted in first principles: solve the money problem first, then address clinical and outcome issues. That’s why our mission is to fix the entire healthcare system, starting with payments.”
Additional Thoughts
Any other topics you would like to discuss? Zekoff concluded:
“We’re hiring. A lot. If you’re a badass who wants to help fix the U.S. healthcare system, you’re technical, you like to work and you want to be in the arena with healthcare providers, we’ve got a great company and role for you.”
