COMPANY INFO
Thoughtful AI's actual company name is Thoughtful Automation Inc. It was founded in 2020 by Alex Zekoff and Dan Parsons. The company has about 33 employees as of the end of 2024 and operates in the AI-powered healthcare administration industry. Their website is www.thoughtful.ai. Thoughtful AI provides an AI operating system designed to automate healthcare revenue cycle management and streamline administrative tasks for healthcare providers, transforming them into AI-powered organizations. The company has raised $20 million in funding and is headquartered in Chicago, United States.
Thoughtful AI is an AI-powered healthcare administration platform focused on automating revenue cycle management and streamlining administrative tasks for healthcare providers. Thoughtful AI was founded in 2020 by Alex Zekoff and Dan Parsons and has quickly established itself as a leader in transforming healthcare organizations into AI-powered enterprises.
The Thoughtful AI leadership team brings together deep expertise in artificial intelligence, healthcare administration, technology, engineering, and customer experience. Together, the management team has cultivated a dynamic culture of innovation, delivering significant advancements in AI-driven solutions for the healthcare industry. The Thoughtful AI executives—led by CEO Alex Zekoff—draw on extensive backgrounds in startup growth, business leadership, product management, and engineering to drive the company’s continued growth and impact.
Alex Zekoff serves as Co-Founder and CEO of Thoughtful AI, where he sets the company’s vision and steers the development of transformative AI solutions in healthcare. Under Alex’s leadership, Thoughtful AI has carved out a leading market position by enabling healthcare providers to automate complex administrative functions, enhancing efficiency and outcomes for both providers and patients. His strategic direction is integral to the company's rapid innovation and growth.
Alex holds an MBA from the University of California, Berkeley, Haas School of Business. He previously contributed as an Applied AI Engineer at Deloitte Consulting (Aerospace and Defense), served on the Board of Directors for the Texas Association of Business, and was a Forbes Technology Council Contributor. This blend of AI, consulting, and industry leadership laid the groundwork for his success as the driving force behind Thoughtful AI’s management team.
Dan Parsons is Co-Founder and Chief Experience Officer of Thoughtful AI, where he is responsible for customer experience and product innovation. Dan has spearheaded user-centric design and engagement strategies, crucially shaping product offerings and driving exceptional customer satisfaction across Thoughtful AI’s client portfolio.
Dan studied at the University of Cincinnati Carl H. Lindner College of Business. Before joining Thoughtful AI, his career included roles as Advisor at 500 Startups, Product positions at BetterUp, and CEO & Co-Founder at DRYV. Dan’s expertise in startup growth and customer experience has been central to establishing a strong company foundation and product-market fit.
Katie Kraft is the Founding Sales Executive at Thoughtful AI, where she has been pivotal in driving sales and deploying AI solutions across a growing portfolio of healthcare organizations. Katie has significantly contributed to the company’s revenue growth and has played a key role in expanding the client base and identifying market opportunities.
Katie graduated with a B.S. in Operations Research & Information Engineering from Cornell University. Previously, she held various sales roles at Databricks, focusing on healthcare and startup markets, and worked in healthcare investment banking at Deutsche Bank. This combination of technical, sales, and analytical experience makes her an essential component of the Thoughtful AI leadership.
Danny Sakka supports clients as a Customer Engineer, ensuring the technical success and seamless implementation of AI solutions. Danny is instrumental in guaranteeing successful product deployments, translating complex technical solutions into impactful client results, and sustaining high customer satisfaction levels.
Danny holds a Bachelor of Arts from Georgetown University and has served in program management and customer success at CloudKitchens. His background in customer engineering and program management brings both technical depth and operational rigor to the management team at Thoughtful AI.
Blake DeBenon is Head of Platform Engineering, providing technical leadership for Thoughtful AI’s core technology infrastructure. Blake oversees the design and scalability of the platform, ensuring robust, reliable, and efficient performance across all AI-driven solutions.
Blake studied at Texas A&M University and has a significant track record in platform engineering and software development, especially in building scalable systems for AI applications. His engineering expertise underpins the company's ability to deliver enterprise-grade solutions.
Will Schwieder leads Product Management and Customer Success at Thoughtful AI, bridging the gap between product development and client engagement. Will aligns the company’s product strategy with emerging market needs and drives customer adoption across healthcare organizations.
Holding an MBA from The University of Chicago Booth School of Business, Will brings a strong background in technical product management and customer success. His career includes leadership roles at Thoughtful AI and other technology companies, further strengthening the company’s management team.
The Thoughtful AI executives combine diverse expertise from business leadership, engineering, healthcare, and product management to form a cohesive and highly effective leadership team. With a clear company structure that places innovation, client success, and technical robustness at its core, Thoughtful AI is well-prepared to lead the evolution of AI-powered healthcare administration. The company’s founders, Alex Zekoff and Dan Parsons, have instilled a culture centered on excellence and rapid growth, supported by an agile and talented management team.
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