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
Actionable
Takeaways
Leverage Operator Experience in Product Development:
Siftwell's success stems from combining deep industry expertise with advanced technology. As Trey explains, many technologists enter healthcare with "cool mousetraps" but don't understand the complexity of problems facing managed care organizations. B2B founders should either deeply learn their target industry or partner with domain experts who can translate technical capabilities into meaningful solutions.
Focus on Results Over Technical Specifications:
While model accuracy matters, Trey emphasizes that customers care more about concrete outcomes like reduced emergency department visits or lower readmission rates. B2B founders should prioritize communicating business impact over technical superiority, especially when selling to C-suite buyers who care about operational results.
Navigate Category Creation Through Problem-Solving:
Rather than forcing themselves into existing categories, Siftwell created their own space by solving specific customer problems. They used the familiar entry point of predictive analytics but differentiated by combining it with deep operational expertise and actionable insights. B2B founders should consider how their unique approach to solving customer problems might transcend traditional category definitions.
Build Go-To-Market Around Industry Context:
In healthcare's highly referential market, Siftwell prioritizes face-to-face interactions, speaking engagements, and leveraging existing relationships. They focus on educating prospects about practical implementation rather than technical complexity. B2B founders should align their marketing strategy with their industry's buying patterns and decision-making culture.
Choose Strategic Investors for Long-Term Success:
Trey emphasizes the importance of founder due diligence in fundraising, particularly in finding investors who understand the industry, company culture, and vision. B2B founders should look beyond capital to ensure their investors can provide relevant expertise and support for their specific market.
Conversation
Highlights
From Health Plan CEO to Healthcare AI Founder: The Tactical Playbook for Winning Enterprise Deals
Most healthcare technology founders enter the market armed with innovative algorithms and bold promises. Few survive first contact with the industry’s reality: that healthcare buyers don’t care about your model’s accuracy—they care about results.
In a recent episode of Category Visionaries, Trey Sutten, CEO and Co-Founder of Siftwell Analytics, a healthcare technology company that’s raised over 5 million in funding, shared how his unconventional path from Medicaid CFO to health plan CEO shaped an entirely different approach to building and selling healthcare AI.
The Operator’s Advantage in an Overhyped Market
When Trey decided to build Siftwell, he wasn’t chasing the AI hype cycle. He was solving a problem he’d lived through as an operator: health plans couldn’t effectively match resources with the right individuals at the right time.
“As we were merging the previous health plan, which was a Medicaid plan, I started to collect the C level executives and say, hey, you know, now that we’re figuring out what our next thing is, what is it that the market needs? Where is their holes?” Trey explained. The answer became Siftwell’s foundation: using machine learning not just to make predictions, but to explain why those predictions matter and what to do about them.
This operator-first mentality shaped everything about Siftwell’s GTM strategy. While competitors focused on touting algorithm accuracy metrics, Trey focused on outcomes. “I think a lot of people, a lot of technologists have entered the healthcare industry and thought that, you know, it was a better model, a better mousetrap that was going to do it. They wanted to talk about accuracy measures like area under the curve or something,” Trey noted. “What I can say, being a former operator, is, yeah, I want you to do that as best as you can. But what way more important to me is getting the results that I’m trying to get.”
Proving Technology Before Selling It
Most founders rush to market with minimum viable products. Trey took a different approach, one informed by his operational background. Before making a single sales pitch, Siftwell needed to prove the technology worked in the real world.
The team acquired sample data sets with millions of lives, ran competitive analyses with data scientists, and identified what differentiated their approach. But the critical step came next: convincing an actual health plan to provide real, live data for pro bono analysis.
“Those early days were really about like, you know, is the advancements that are being made in machine learning and artificial intelligence, can they truly be applied in the context of healthcare?” Trey said. “And the answer resoundingly came back yes.”
That pro bono client eventually converted to paying customer—validation that the technology delivered on its promises. This methodical approach to product-market fit gave Trey the confidence to scale, but more importantly, it gave him credible proof points for future sales conversations.
Speaking the Language: The Unfair Competitive Advantage
At Digital Health New York, Trey witnessed something that crystallized Siftwell’s competitive moat. During a panel discussion, founders in the audience stopped the conversation to ask for explanations of basic healthcare acronyms.
“The acronyms were so fundamental to healthcare and so basic to healthcare that I was actually surprised that somebody was pausing us to get an explanation,” Trey recalled. His advice to healthcare technology founders was unequivocal: “Learn the space or learn one space and really focus on it.”
This deep domain expertise became Siftwell’s GTM weapon. “What gets us into the door oftentimes is the fact that we are, you know, a number of the members on the team are former managed care operators, and we speak the language, we know the problems,” Trey explained.
For Siftwell, this meant sales conversations centered on managed care challenges, not technology features. When prospects discussed utilization management, readmission rates, or member engagement, Trey could respond not as a vendor, but as someone who’d faced those exact problems from the operator’s chair.
Category Positioning: When Being Different Matters More Than Being Better
Siftwell operates in the predictive analytics category, but Trey deliberately positions the company as something different. “We broadly fall under the category of predictive analytics, but we’re an entirely different animal, Brett,” he explained.
The distinction matters because traditional analytics solutions focused on predictions without context. Siftwell goes deeper: “We’re taking really deep and battle tested managed care experience, combining it with these advanced Technologies to not only point out who they should focus on, but why they should focus on and even what they should do in order to better engage them.”
This positioning allowed Siftwell to capture demand from buyers searching for predictive analytics while differentiating on the dimensions operators actually cared about: actionable insights, not just accurate models.
The Referential Market Playbook
Healthcare isn’t a market you crack with digital marketing funnels and SEO plays. Trey’s GTM strategy centered on what works in highly referential markets: relationships, face-to-face interactions, and education.
“For us it’s a highly referential market, you know, so it’s getting out there, it’s relying on long standing relationships that you had, it’s being face to face,” Trey said. “I spent a lot of my time on the road interacting with our existing customers, making connections with new customers, panels, speaking opportunities, or just, you know, direct meetings with individuals or teams.”
But the face-to-face approach served a specific purpose beyond relationship building. Trey used these interactions to dismantle misconceptions that prevented buyers from acting. “There’s a lot of misconceptions around some obstacles that people think that they’ve got,” he explained. “Getting out there, educating people on this isn’t really big and scary tech, but rather you can get started today and in fact you need to.”
Due Diligence Works Both Ways
When it came to fundraising, Trey learned that founder due diligence on investors matters as much as investor due diligence on founders. “How important it is to do your due diligence as a Founder,” he emphasized. “I have often heard about founders getting funding. That was the exciting piece. But then there was a mismatch between what the company actually needed and who ended up on their board.”
For Siftwell’s next funding round, Trey’s focus extends beyond capital to alignment: “Making sure that there’s the experience match, there’s the industry expertise match, that there’s a cultural match, all the rest of it that we eventually are going to be working with, understand what we’re building, how we’re building it and why we’re building it.”
Building Toward Agentic AI
Looking ahead, Trey’s vision for Siftwell extends beyond predictions to autonomous action. “I imagine a future, Brett, and we’re building it where I can tell you who’s not going to get a cancer screening. I can contextualize them, including the level of rurality. I can spin up care plan associated with that member, that individual member,” he explained.
The vision includes automatically shipping screening kits to rural patients, scheduling appointments for urban members, and brokering provider-patient exchanges—all triggered by AI predictions. “That’s the future that I want to build and that we’re already building,” Trey said.
For healthcare technology founders, Trey’s journey offers a clear lesson: in a market drowning in AI hype, domain expertise and operator empathy create defensible competitive advantages. The best healthcare technology doesn’t just make accurate predictions—it speaks the language of the buyer, solves their actual problems, and delivers measurable results.
Recommended Founder
Interviews
Alexandra Ferraro
Head of Marketing of Intelligencia AI
Beyond Perfect: Healthcare Tech Marketing That Drives Real Revenue
Omer Maman
VP of Marketing of Healthee
Why AI Should Enhance, Not Replace Your Marketing Team
Vicky Demas
CEO of Identifeye Health
Vicky Demas, CEO of identifeye HEALTH: $90 Million Raised to Power the Future of Retinal Imaging
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
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
Michael Passanante
Senior Vice President of Marketing and Communications of Capital Rx
How to Build 18-Month Attribution Models That Actually Work
Matt Renfro
Co-Founder & CEO of Lynx
Matt Renfro, CEO of Lynx: $17.5 Million raised to Bring Modern Fintech to Healthcare
Jocelyn Nowak
Marketing & Sales Enablement Lead of FIGUR8
Integrity-Driven Marketing: FIGUR8’s Path to 3,000+ Clinics
Verena Gerhardus
Director of Growth of Nelly Solutions
How Nelly Grew 3X Through Meta Ads in Health Tech
Joseph Schneier
CEO of Trusty Care
Joseph Schneier, CEO of Trusty Care: $13+ Million Raised to Shape the Future of Medicare
Daniel West
CEO of Prospection
Daniel West, CEO of Prospection: $36 Million Raised to Build the Future of Patient-Centric Intelligence
Ty Allen
CEO of SocialClimb
Ty Allen, CEO of SocialClimb: $12 Million Raised to Power the Future of Healthcare Marketing
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
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
Nabeel Kaukab
Founder and CEO of Phamily
How Phamily built an eight-figure ARR healthcare company without discounting: The subsidized R&D approach | Nabeel Kaukab ($25M Raised)
Elizabeth Wiet
Senior Vice President Marketing of VieCure
Why This Healthcare Marketer Is Abandoning Trade Show Booths w Elizabeth Wiet
Nick Soman
CEO & Founder of Decent
Nick Soman, CEO & Founder of Decent: $43 Million Raised to Build the Future of Direct Primary 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
Austin McChord
CEO of Casana
Austin McChord, CEO of Casana: Over $46 Million Raised to Create the Future of In-Home Health Monitoring
Joe Gagnon
CEO of 1upHealth
Joe Gagnon, CEO at 1upHealth: Over $75 Million Raised to Build the Future of Healthcare Data
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
Daniel Lambert
CEO of PathologyWatch
Daniel Lambert, CEO of PathologyWatch: Over $50 Million Raised to Build the Future of Digital Pathology
Arif Nathoo
CEO and Co-Founder of Komodo Health
Arif Nathoo: the Story of Komodo Health ($3 Billion Valuation)
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
Mike Desjadon
CEO of Anomaly
Why Anomaly avoids annual curiosity revenue (ACR) — and you probably should to | Mike Desjadon ($30M Raised)
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
Mark Lehmkuhle
CEO & Founder of Epitel
Mark Lehmkuhle, CEO & Founder of Epitel: $20 Million Raised to Build the Future of Brain Health Monitoring
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
Gregory Stein
CEO of Shadowbox
How Shadowbox evolved it’s ICP from desperate labs to health systems with 500-1,000 community providers | Gregory Stein
Teodor Grantcharov
Founder of Surgical Safety Technologies Inc.
How Surgical Safety Technologies targeted the most challenging customers first (massive hospitals) | Teodor Grantcharov
Rebecca McNeil
VP of Marketing of SureCost
Why This VP of Marketing Abandoned Paid Media Completely
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
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
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
Kevin Flyangolts
CEO and Founder of Aclid
Kevin Flyangolts, CEO & Founder of Aclid: $4 Million Raised to Build the Future of Biosecurity
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
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
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
Todd Zion
Founder of Akston Biosciences
Todd Zion, Founder of Akston Biosciences: From a $500M Exit to Pioneering Biotech Innovation in Pet Health
Corey Washington
Senior Marketing Manager of Amenities Health
Humanizing Healthcare Tech: Marketing Lessons from Amenities
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
Amar Kendale
President and Co-Founder of Homeward
Amar Kendale, President & Co-Founder of Homeward: $70 Million Raised to Transform Rural Healthcare Through Technology
Veer Gidwaney
CEO & Founder of Ansel Health
Veer Gidwaney, CEO & Founder of Ansel Health: $50 Million Raised to Transform Supplemental Health Insurance
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
Amy Brown
CEO and Founder of Authenticx
Amy Brown, CEO and Founder of Authenticx: $28 Million Raised to Build the Future of Listening AI
Avi Singer
CEO & Founder of Showd.me
Avi Singer, CEO & Founder of Showd.me: $4.5 Million Raised to Build the Future of Compliance Training
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
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)
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
Brandon Young
CMO of Garner Health
Why Marketing Lost Its Craft (And How AI Could Force It Back)
Alex Zekoff
CEO and Co-Founder of Thoughtful AI
Alex Zekoff, CEO and Co-Founder of Thoughtful AI: $21 Million Raised to Power the Future of Healthcare Automation
Dilpreet Sahota
CEO of Trek Health
Dilpreet Sahota, CEO of Trek Health: $3 Million Raised to Help Mental Health Providers Accept Insurance
Jack McInnes
Director of Marketing of Corti AI
Building Developer Trust in Healthcare AI Without Hype
David King Lassman
Founder of GigXR
David King Lassman, Founder of GigXR: $7 Million Raised to Bring Immersive Learning to Healthcare
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
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
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
Brett Kleger
CEO of Datacubed Health
Brett Kleger, CEO of Datacubed Health: $43 Million Raised to Revolutionize Clinical Trial Data Collection
Kristen Valdes
CEO & Founder of B.well
Kristen Valdes, CEO & Founder of B.well: $100 Million Raised to Reimagine the Healthcare Experience
Armon Sharei
CEO & Founder of Portal
Armon Sharei, CEO & Founder of Portal: $5 Million Raised to Power the Future of Cell Engineering
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
Thomas Knox
CEO & Founder of VitVio
Thomas Knox, CEO & Founder of VitVio: $10 Million Raised to Transform Surgical Operations Through AI-Powered Automation
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
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
Marshall Darr
CEO & Co-Founder of StretchDollar
How StretchDollar drives leads from LLM search | Marshall Darr
Ignacio Medrano
Founder & CMO of Savana
Ignacio Medrano, Founder & CMO of Savana: $44M Raised to Transform Healthcare Intelligence Through AI
Cody Simmons
CEO of DermaSensor
Cody Simmons, CEO of DermaSensor: $36 Million Raised to Build the First AI-Powered Skin Cancer Detection Tool for Primary Care
Ian Prendergast
CEO and Co-Founder of Toothio
How Toothio built credibility as non-industry founders through strategic SME hires | Ian Prendergast
Khaled Boukadoum
Founder of Torch Dental
Khaled Boukadoum, Founder of Torch Dental: $49.5 Million Raised to Transform Dental Supply Management Through Digital Innovation
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
Senan Ebrahim
CEO & Founder of Delfina
Senan Ebrahim, CEO & Founder of Delfina: $10 Million Raised to Build the Future of Intelligent Pregnancy Care
Danny Freed
CEO & Founder of Blueprint
Danny Freed, CEO & Founder of Blueprint: $13.7 Million Raised to Build the Future of Therapist Enablement
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
Brad Kittredge
CEO & Co-Founder of Brightside
Brad Kittredge, CEO & Co-Founder of Brightside: $150 Million Raised to Build the Future of Mental Healthcare
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
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
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