Ready to build your own Founder-Led Growth engine? Book a Strategy Call
Frontlines.io | Where B2B Founders Talk GTM.
Strategic Communications Advisory For Visionary Founders
Conversation
Highlights
Data-Driven Pivots: How Thoughtful AI Found Its Healthcare Sweet Spot
Most founders dream of product-market fit. Few have the discipline to discover it through rigorous data analysis. In a recent episode of Category Visionaries, Alex from Thoughtful AI shared how mining customer data revealed their true market opportunity – and how being an industry outsider helped them seize it.
The journey began with a classic startup scenario: a promising solution searching for its perfect problem. “When we first started the model we created, were a notorious amazing solution, but didn’t really have a problem set that was compelling for it,” Alex recalls. Like many early-stage companies, they cast a wide net, selling automation solutions across multiple industries.
By 2022, they had accumulated a diverse portfolio of 85 robots deployed across 35 customers in various sectors. Instead of continuing to spread thin, they took a critical pause to analyze their data. “We looked at all of our robots…trying to figure out where is product market fit, like, which one of our robot segments are the highest ROI,” Alex explains.
The numbers told a clear story. Their healthcare implementations were delivering staggering results: “We looked under the hood and all of our mid market healthcare companies, the robots were 1000% ROIs. They were spending 200% net revenue retention.” This discovery prompted a decisive pivot to focus exclusively on healthcare providers.
But the real insight wasn’t just about which market to serve – it was about how to serve it. Coming from an aerospace and defense background, Alex approached healthcare with fresh eyes: “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. First principles of what’s the core problem here, and how are we solving it best for the customer experience?”
This outsider perspective helped them reimagine how automation technology could be sold and implemented. Rather than following the traditional enterprise software playbook of separate licenses, implementation partners, and internal teams, they consolidated everything into a single offering. “We are your internal team, we are your implementer, and we are your technology,” Alex explains. “And that means the price is one price. So when you buy us, it’s very easy to model ROI.”
They’ve also taken a bold stance on aligning incentives. “We actually have clauses state that you don’t have to pay us until we achieve those outcomes,” Alex notes. This approach has resonated strongly with healthcare executives focused on concrete metrics like cash flow and collections.
The company’s commitment to quality over quantity extends to their growth strategy. “That’s why we’re only selling one customer a month. That’s our capacity right now,” Alex shares. “And we tell our customers we’re committed to quality and excellence, not just pushing seats, pushing pools.”
This disciplined approach is backed by ambitious but focused goals: “We believe getting to 100 million ARR, 100 customers, we can achieve that by 2026.” To maintain their high-touch service model while scaling, they’re investing heavily in internal AI tooling. “We actually believe we have a strategy. The company is 100 million ARR, 100 customers, 100 employees.”
The story of Thoughtful AI offers valuable lessons for founders navigating their own path to product-market fit. First, let data guide your focus – even if it means pivoting away from existing customers. Second, being an industry outsider can be an advantage if you approach it with genuine curiosity and first principles thinking. Finally, don’t be afraid to challenge conventional business models if you can deliver better outcomes for customers.
As Alex puts it: “We realize that innovation is happening at a much faster rate…so we need to stay ahead of the curve.” By remaining focused on their healthcare niche while continually investing in R&D, they’re positioning themselves for sustainable long-term growth rather than just chasing short-term expansion.
Actionable
Takeaways
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.
Recommended Founder
Interviews
Joshua Miller
CEO and Co-Founder of Gradient Health
Joshua Miller, CEO & Co-Founder of Gradient Health: $5.7 Million Raised to Build the Future of Medical Imaging
Vicky Demas
CEO of Identifeye Health
Vicky Demas, CEO of identifeye HEALTH: $90 Million Raised to Power the Future of Retinal Imaging
Aasim Saeed
CEO and Founder of Amenities Health
Aasim Saeed, CEO and Founder of Amenities Health: $10 Million Raised to Build the Future of Patient Engagement
Austin McChord
CEO of Casana
Austin McChord, CEO of Casana: Over $46 Million Raised to Create the Future of In-Home Health Monitoring
Amar Kendale
President and Co-Founder of Homeward
Amar Kendale, President & Co-Founder of Homeward: $70 Million Raised to Transform Rural Healthcare Through Technology
Torben Nielsen
CEO & Co-Founder of Uptiv Health
Torben Nielsen, CEO of Uptiv Health: $7.5M Raised to Build the Future of Infusion Therapy Through Technology-Enabled Retail Centers
David Berry
CEO and Founder of Valo
David Berry, CEO and Founder of Valo: Over $500 Million Raised to Build the Future of Drug Discovery
Joseph Schneier
CEO of Trusty Care
Joseph Schneier, CEO of Trusty Care: $13+ Million Raised to Shape the Future of Medicare
Brad Kittredge
CEO & Co-Founder of Brightside
Brad Kittredge, CEO & Co-Founder of Brightside: $150 Million Raised to Build the Future of Mental Healthcare
Henry O’Connell
CEO & Founder of Canary Speech
Henry O’Connell, CEO & Founder of Canary Speech: $26 Million Raised to Build the Future of Vocal Biomarker Technology
Joe Gagnon
CEO of 1upHealth
Joe Gagnon, CEO at 1upHealth: Over $75 Million Raised to Build the Future of Healthcare Data
Rafid Fadul
CEO and Co-Founder of Zivian Health
Rafid Fadul, CEO and Co-Founder of Zivian Health: $3 Million Raised to Power the Future of Compliant Healthcare Collaborations
Kevin Flyangolts
CEO and Founder of Aclid
Kevin Flyangolts, CEO & Founder of Aclid: $4 Million Raised to Build the Future of Biosecurity
Dimitrios Skaltsas
CEO & Co-Founder of Intelligencia AI
Dimitrios Skaltsas, CEO & Co-Founder of Intelligencia AI: $15.5 Million Raised to Build the Future of Drug Development
Michael Chang
Mastering Market Fit in AI: Insights from Michael Chang, Director of Marketing at ArteraAI
Daniel Lambert
CEO of PathologyWatch
Daniel Lambert, CEO of PathologyWatch: Over $50 Million Raised to Build the Future of Digital Pathology
Danny Freed
CEO & Founder of Blueprint
Danny Freed, CEO & Founder of Blueprint: $13.7 Million Raised to Build the Future of Therapist Enablement
Itzik Cohen
Co-Founder and CEO of PayZen
Itzik Cohen, Co-Founder and CEO of PayZen: $240 Million Raised to Build the Future of Affordable Health Care
James Bates
CEO and Founder of AdviNOW Medical
James Bates, CEO and Founder of AdviNOW Medical: $24 Million Raised to Build the Future of AI-Powered Healthcare
Thomas Knox
CEO & Founder of VitVio
Thomas Knox, CEO & Founder of VitVio: $10 Million Raised to Transform Surgical Operations Through AI-Powered Automation
Senan Ebrahim
CEO & Founder of Delfina
Senan Ebrahim, CEO & Founder of Delfina: $10 Million Raised to Build the Future of Intelligent Pregnancy Care
Rishi Nayyar
CEO and Co-Founder of PocketHealth
Rishi Nayyar, CEO and Co-Founder of PocketHealth: $22.5 Million Raised to Power the Future of Medical Image Sharing
Matthew Stoudt
CEO and Founder of AppliedVR
Matthew Stoudt, CEO and Founder of AppliedVR: Over $70 Million Raised to Build the Future of Chronic Pain Relief
Matt Renfro
Co-Founder & CEO of Lynx
Matt Renfro, CEO of Lynx: $17.5 Million raised to Bring Modern Fintech to Healthcare
Kristen Valdes
CEO & Founder of B.well
Kristen Valdes, CEO & Founder of B.well: $100 Million Raised to Reimagine the Healthcare Experience
Andreas Cleve
CEO and Co-Founder of Corti
Andreas Cleve, CEO and Co-Founder of Corti: $32 Million Raised to Power the Future of Patient Consultations
Michael Gorton
Founder of Teladoc
Teladoc Founder Michael Gorton on the Early Days of Pioneering the Telemedicine Category (And What’s He’s Up to Next)
Amy Brown
CEO and Founder of Authenticx
Amy Brown, CEO and Founder of Authenticx: $28 Million Raised to Build the Future of Listening AI
Dr. Nan-Wei Gong
CEO and Founder of FIGUR8
Dr. Nan-Wei Gong, CEO & Founder of FIGUR8: $40 Million Raised to Build the Future of Musculoskeletal Health and Injury Data Solutions
Trenor Williams
CEO and Co-Founder of Socially Determined
Trenor Williams, CEO and Co-Founder of Socially Determined: $34 Million Raised to Build the Social Risk Intelligence Category
Kyle Kiser
CEO of Arrive Health
Kyle Kiser, CEO of Arrive Health: Over $40 Million Raised to Improve the Value of Healthcare Through Informed Decision-Making
Ignacio Medrano
Founder & CMO of Savana
Ignacio Medrano, Founder & CMO of Savana: $44M Raised to Transform Healthcare Intelligence Through AI
Todd Zion
Founder of Akston Biosciences
Todd Zion, Founder of Akston Biosciences: From a $500M Exit to Pioneering Biotech Innovation in Pet Health
Kourosh Davarpanah
Co-Founder and CEO of Inato
Kourosh Davarpanah, Co-Founder and CEO of Inato: Over $35 Million Raised to Build the Future of Clinical Trials
Richard Queen
CEO and Co-Founder of DignifiHealth
Richard Queen, CEO and Co-Founder of DignifiHealth: $7 Million Raised to Drive Better Patient Outcomes in Rural Healthcare and Beyond
Derek Streat
Co-Founder & Chief Executive Officer of Dexcare
Derek Streat, CEO of Dexcare: $110 Million Raised to Help Health Systems to Find Time for the Best Care
Justin Dearborn
Founder & CEO of Praia Health
Justin Dearborn, Founder & CEO of Praia Health: $20 Million Raised to Build the Future of Consumer Experience in Healthcare
Alexandra Ferraro
Head of Marketing of Intelligencia AI
Beyond Perfect: Healthcare Tech Marketing That Drives Real Revenue
David King Lassman
Founder of GigXR
David King Lassman, Founder of GigXR: $7 Million Raised to Bring Immersive Learning to Healthcare
Daniel West
CEO of Prospection
Daniel West, CEO of Prospection: $36 Million Raised to Build the Future of Patient-Centric Intelligence
Dilpreet Sahota
CEO of Trek Health
Dilpreet Sahota, CEO of Trek Health: $3 Million Raised to Help Mental Health Providers Accept Insurance
Brett Kleger
CEO of Datacubed Health
Brett Kleger, CEO of Datacubed Health: $43 Million Raised to Revolutionize Clinical Trial Data Collection
Verena Gerhardus
Director of Growth of Nelly Solutions
How Nelly Grew 3X Through Meta Ads in Health Tech
Dipanwita Das
CEO and Co-Founder of Sorcero
Dipanwita Das, CEO and Co-Founder of Sorcero: Over $20 Million Raised to Power Medical Affairs Teams of the Future
Mark Lehmkuhle
CEO & Founder of Epitel
Mark Lehmkuhle, CEO & Founder of Epitel: $20 Million Raised to Build the Future of Brain Health Monitoring
Nick Soman
CEO & Founder of Decent
Nick Soman, CEO & Founder of Decent: $43 Million Raised to Build the Future of Direct Primary Care
Corey Washington
Senior Marketing Manager of Amenities Health
Humanizing Healthcare Tech: Marketing Lessons from Amenities
Ben Albert
CEO & Co-Founder of Upfront Healthcare
Ben Albert, CEO & Co-Founder of Upfront Healthcare: $30 Million Raised to Power the Future of Patient Engagement
Brock Leonti
CEO & Co-Founder of Prescribe FIT
Brock Leonti, CEO & Co-Founder of Prescribe FIT: $15 Million Raised to Build the Future of Orthopedic Care
Viral Patel
Founder and CEO of Radish Health
Viral Patel, CEO of Radish Health: $5 Million Raised to Connect Employees with a Better Healthcare Experience
Dr Thomas Oakley
CEO of Feedback PLC
Dr Thomas Oakley, CEO of Feedback PLC: £20 Million Raised to Build the Future of Patient Data Sharing
Alfred Griffin
CEO and Co-Founder of CEO and Co-Founder
Alfred Griffin, CEO and Co-Founder of LightForce: $150 Million Raised to Power the Future of Orthodontics
Veer Gidwaney
CEO & Founder of Ansel Health
Veer Gidwaney, CEO & Founder of Ansel Health: $50 Million Raised to Transform Supplemental Health Insurance
Armon Sharei
CEO & Founder of Portal
Armon Sharei, CEO & Founder of Portal: $5 Million Raised to Power the Future of Cell Engineering
Jocelyn Nowak
Marketing & Sales Enablement Lead of FIGUR8
Integrity-Driven Marketing: FIGUR8’s Path to 3,000+ Clinics
Hala Borno
Founder and CEO of Trial Library
Hala Borno, Founder and CEO of Trial Library: $5M Raised to Improve Patient Recruitment and Diversity in Oncology Clinical Trials
Elad Ferber
CEO & Co-Founder of Synthpop
Elad Ferber, CEO & Co-Founder of Synthpop: $8 Million Raised to Build the Future of Healthcare Administration with AI
Khaled Boukadoum
Founder of Torch Dental
Khaled Boukadoum, Founder of Torch Dental: $49.5 Million Raised to Transform Dental Supply Management Through Digital Innovation
Stacy Edgar
CEO and Co-Founder of Venteur
Stacy Edgar, CEO & Co-Founder of Venteur: $7.6 Million Raised to Build the Future of Health Insurance
Trey Sutten
CEO & Co-Founder of Siftwell Analytics
Trey Sutten, CEO & Co-Founder of Siftwell Analytics: $5 Million Raised to Transform Healthcare Analytics with AI-Powered Predictions
Cesar Herrera
CEO and Co-Founder of Yuvo Health
Cesar Herrera, CEO and Co-Founder of Yuvo Health: $28 Million Raised to Revolutionize Healthcare Access
Samson Magid
Co-Founder and CEO of HealthSnap
Samson Magid, Co-Founder and CEO of HealthSnap: Over $12 Million Raised to Build the Future of Remote Patient Monitoring
Ty Allen
CEO of SocialClimb
Ty Allen, CEO of SocialClimb: $12 Million Raised to Power the Future of Healthcare Marketing