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Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech’s most innovative B2B founders. In today’s episode, we’re speaking with Alex Zekoff, CEO and co-founder of Thoughtful AI, an AI-powered healthcare automation platform that has raised $21 million in funding.

  • Thoughtful AI uses software robots as augmented revenue cycle employees to help healthcare providers collect more money faster, increasing cash flow by up to 30%.
  • As an industry outsider coming from aerospace, Alex brings a beginner’s mindset to reimagining healthcare administration, focusing obsessively on customer needs and processes.
  • Thoughtful AI differentiates through white-glove service, custom solutions that work with existing tech stacks, and outcome-based contracts tied to measurable ROI.
  • To scale from 1 customer launch per month to 1 per week, Alex is investing heavily in R&D and AI-powered internal tools to maintain quality and satisfaction as volume grows.
  • With a $15K/month starting contract, Thoughtful AI aims to reach $100M ARR and 100 customers by 2026, while remaining cash flow positive.
  • Alex’s long-term vision is to expand the automation platform to other sectors like government and Fortune 500 after establishing a billion-dollar healthcare franchise.


Embrace Beginner's Mind to Reimagine Legacy Industries:

As an outsider to healthcare, Alex approached the notoriously complex and change-resistant industry with fresh eyes. By focusing relentlessly on customer needs and existing processes, Thoughtful AI built a solution that slots in seamlessly to drive immediate results. Founders should lean into their beginner's mind and challenge legacy assumptions when tackling entrenched sectors.

Invest in R&D to Systematize Bespoke Services:

Thoughtful AI's white-glove, custom-built approach has been key to landing and expanding enterprise accounts. But Alex recognizes this high-touch model must be tempered with robust internal systems to reach scale. By using AI to augment everything from customer onboarding to ongoing support, Thoughtful AI aims to maintain its personal touch while accelerating growth. Founders should balance artisanal experiences with automated engines.

Tie Pricing to Measurable Business Outcomes:

To build trust with enterprise buyers, Thoughtful AI directly links its fees to the ROI it generates for customers. By putting skin in the game and getting paid on results, the company creates aligned incentives and mitigates perceived risk. Founders should explore performance-based pricing models that demonstrate real value creation for clients and boost their confidence to buy.

Sequence Your Expansion From Beachhead to Bowling Alley:

While Thoughtful AI's automation platform has horizontal applicability, Alex is laser-focused on dominating the healthcare market before pursuing other sectors. By establishing a reference customer base and playbook in a trillion-dollar market, the company will have the traction and credibility to attack adjacent industries. Founders should sequence their expansion plans to balance focus and optionality.

Plan Proactively for Technological Disruption:

Even as Thoughtful AI rides the first wave of AI-powered automation, Alex and his team are already preparing for the next phase of innovation. By collecting rich process metadata, they are primed to harness emerging large language models and other AI capabilities to extend their platform. Founders must peer beyond the horizon to anticipate how their solutions may be enhanced or disrupted and plan accordingly.

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