5 Go-to-Market Lessons from Thoughtful AI’s Path to Product-Market Fit

5 Go-to-Market Lessons from Thoughtful AI’s Path to Product-Market Fit

When does casting a wide net become a liability? In a recent episode of Category Visionaries, Alex Zekoff from Thoughtful AI shared how focusing on data-driven decisions and customer outcomes transformed their go-to-market strategy. Here are the key lessons from their journey:

1. Let Data Guide Your Focus Early success can mask bigger opportunities. Initially, Thoughtful AI sold automation solutions across multiple sectors, from legal to real estate. But when they analyzed their deployment data, a clear pattern emerged. “We looked at all of our robots. We had about 85 live robots in production systems across our 35 customers,” Alex explains. “All of our mid market healthcare companies, the robots were 1000% ROIs. They were spending 200% net revenue retention.” This discovery led to their healthcare pivot, demonstrating how rigorous data analysis can reveal your true market opportunity.
2. Simplify Your Value Proposition Enterprise software sales often involve multiple vendors and complex pricing structures. Thoughtful AI broke this mold by consolidating everything into one offering. “We are your internal team, we are your implementer, and we are your technology,” Alex notes. “And that means the price is one price. So when you buy us, it’s very easy to model ROI.” This simplified approach makes it easier for customers to understand and justify their investment.
3. Align Incentives with Outcomes Instead of traditional licensing models, Thoughtful AI tied their success directly to customer results. “We actually have clauses state that you don’t have to pay us until we achieve those outcomes,” Alex reveals. This bold approach demonstrates confidence in their solution while reducing customer risk. They focused on metrics that executives care about, particularly in healthcare: “Executives in healthcare, they care about cash flow, they care about collecting more money.”
4. Scale with Intention Rather than chase rapid growth, Thoughtful AI deliberately limits new customer acquisition. “That’s why we’re only selling one customer a month. That’s our capacity right now,” Alex shares. “We tell our customers we’re committed to quality and excellence, not just pushing seats.” This disciplined approach ensures they can maintain service quality while building sustainable growth.
5. Leverage the Outsider’s Advantage Coming from aerospace and defense, Alex approached healthcare without preconceptions: “I love it because I have no preconceived notions in healthcare of how it’s supposed to be done. So I come with a beginner’s mindset every day.” This fresh perspective enabled them to challenge industry norms and introduce innovative solutions.

Looking ahead, Thoughtful AI maintains ambitious but focused goals: “We believe getting to 100 million ARR, 100 customers, we can achieve that by 2026.” Their strategy emphasizes quality over quantity, targeting “100 million ARR, 100 customers, 100 employees.”

For founders navigating their own go-to-market strategy, these lessons highlight the importance of letting data drive decisions, simplifying complex offerings, and maintaining high standards even as you scale. As Alex emphasizes, “We realize that innovation is happening at a much faster rate…so we need to stay ahead of the curve.”

The key takeaway? Success often comes not from trying to serve everyone, but from identifying and doubling down on where you create exceptional value. By focusing intensely on healthcare and maintaining strict quality standards, Thoughtful AI has turned what could have been a limitation into a competitive advantage.