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
Target customers facing existential financial pressure, not optimal market conditions:
Shadowbox entered through lab diagnostics—a commoditized, low-margin segment hemorrhaging money where providers faced $5K-$50K integration costs per connection taking 3-6 months. Greg acknowledged labs are "the redheaded stepchild of healthcare" but their desperation made them willing to pilot unproven technology. The lesson: segments with severe unit economics problems become early adopter pools because status quo costs exceed perceived risk of new vendors.
Build a partnerships function before you have market leverage:
Shadowbox hired a partnerships-focused employee early to cultivate relationships with RCM vendors and lab information system providers already selling to target customers. Rather than waiting for customer traction to attract partners, they used partnerships to generate initial traction. Greg emphasized healthcare adoption requires credible references—partnerships provide instant credibility entrepreneurs can't buy. Map your ecosystem's existing vendor relationships and pursue co-sell arrangements before achieving meaningful ARR.
Use early customer feedback to migrate upmarket, not pivot laterally:
Shadowbox started with labs, expanded to imaging centers, but their true ICP emerged as health systems with 500-1,000 community providers on disparate EHRs where traditional integration economics break down. Greg noted: "health systems that have major outreach programs where it doesn't pencil out to have them on their EPIC system." The migration path moved from small, desperate customers toward larger organizations facing the same core problem at scale. Don't mistake initial ICP for ultimate ICP—use early segments as beachheads to validate technology before pursuing customers with better economics.
Partner with horizontal competitors when you solve orthogonal use cases:
The HC1 deal splits the interoperability market—structured, predictable integrations go to HC1's traditional approach while rapid deployments to fragmented provider networks go to Shadowbox. This isn't channel partnership but market segmentation by use case economics. Greg explained they bring "something complementary to and in some ways competitive" but combined create offerings competitors can't match. Evaluate whether your "competitors" actually serve different jobs-to-be-done within the same category, then structure partnerships around use case delineation rather than territorial splits.
Leverage policy expertise as product moat in regulated markets:
Greg's Capitol Hill background enabled Shadowbox to support the Coalition for Innovative Lab Testing's successful lawsuit blocking FDA regulation of lab-developed tests—directly protecting their customers' business models. This wasn't marketing but strategic positioning that demonstrates commitment beyond vendor relationships. In heavily regulated industries, founders with policy expertise or advisors who can shape regulatory outcomes create defensibility that pure technology cannot. Consider how industry advocacy amplifies customer loyalty while potentially expanding TAM through favorable regulatory changes.
Conversation
Highlights
How Shadowbox Turned Healthcare’s Least Profitable Segment Into a $950B Market Entry Point
Healthcare providers waste nearly $1 trillion annually on manual processes—not $300 billion as commonly cited, but $950 billion according to testimony before the U.S. Senate. The problem isn’t workflow inefficiency. It’s infrastructure economics: accessing siloed EHR data costs $5,000 to $50,000 per integration and takes three to six months to implement.
In our recent episode of Category Visionaries, Gregory Stein, CEO of Shadowbox, explained how his company built patented browser technology that accesses the document object model and API endpoints within EHR systems, enabling integration in five minutes rather than months. But the more instructive story is how they went to market in a system designed to resist exactly what they’re selling.
Targeting Financial Desperation Instead of Buying Power
In 2017, Shadowbox had validated technology and multiple potential segments to pursue. Gregory chose laboratory diagnostics—the segment every other vendor avoids.
“The lab industry is like the most volatile,” Gregory explains. “They go in and out of business, they have terrible margin. It’s sort of the, you know, to use a pejorative term, the redheaded stepchild, if you will, of the healthcare system. Nobody likes lab. They’re always first one to go.”
The calculation was deliberate. Labs couldn’t afford $5,000-$50,000 integrations with 3-6 month timelines. Their unit economics were so broken that maintaining the status quo threatened their survival. Gregory recognized that “because labs are under such financial duress and such challenge from insurance companies, they were willing to take a flyer on an unproven technology with an unproven leader.”
This inverts conventional market entry logic. Standard wisdom says target segments with healthy margins and established budgets. Shadowbox targeted customers where the pain of doing nothing exceeded the perceived risk of adopting unproven technology from an unknown vendor.
The lesson isn’t “target unprofitable segments.” It’s understanding when dire unit economics create adoption windows that don’t exist in healthier markets. The key variable is whether your solution addresses the specific financial constraint causing the desperation.
First-Touch Product Validation
Shadowbox launched their first customer in 2018. When the medical assistant responsible for ordering tests hit the button labeled “order now,” the form auto-populated with patient data extracted from the EHR through Shadowbox’s browser.
“Her face just lit up and she said, this is going to save me so much time,” Gregory recalls. “Because otherwise I’m filling out either on paper and if it’s wrong, then I’m getting phone calls from the lab and it’s just a huge hassle.”
That interaction validated more than technical functionality. It confirmed that value was immediately visible without explanation, the alternative was painful enough that adoption required no persuasion, and the improvement was dramatic enough to create instant advocacy.
Building Partnership Infrastructure Pre-Traction
Most startups pursue partnerships after establishing market presence. Shadowbox hired for partnerships as an early function—before they had leverage to offer potential partners.
The target: revenue cycle management vendors and lab information system providers already selling to Shadowbox’s ICP. These partners faced the same integration economics problem. When prospects couldn’t afford traditional integrations, partners could position Shadowbox as an alternative deployment path.
“Getting your foot in the door with a credible partner as a reference is probably the most important thing in healthcare,” Gregory emphasizes. “Healthcare is one of the slowest to adopt industries out there.”
The strategy created a distribution mechanism before Shadowbox had the brand recognition or customer base to generate meaningful inbound volume. Partners provided both customer access and category credibility simultaneously.
Using Unprofitable Segments as Technology Beachheads
Labs validated Shadowbox’s core technology and generated initial revenue. But Gregory recognized the ultimate ICP differed significantly: “The true ICP, I think, ultimately are health systems that have major outreach programs where they have hundreds if not thousands of community providers, where it doesn’t pencil out to have them on their EPIC system or their Oracle server system.”
This articulates the beachhead-to-expansion path clearly. Labs had the same core problem—fragmented EHR access—but lacked resources for traditional solutions. Health systems have the same problem at dramatically larger scale: 500 to 1,000 community providers on disparate EHR systems where traditional integration would cost millions and require years to implement.
Shadowbox moved from labs to imaging centers, progressively building toward health systems. Each segment provided validation for entering the next tier. The technology that worked for resource-constrained labs could handle enterprise-scale provider network complexity.
Market Segmentation Through Use Case Economics
In July, Shadowbox announced a partnership with HC1, a company approximately five to six times their size that serves roughly 20% of U.S. health systems. HC1 provides traditional interoperability through HL7 and API integrations—ostensibly competitive with Shadowbox’s approach.
The partnership functions because they solve orthogonal use case economics. “We’re able to split the market, if you will, in terms of use cases that rely or require an HL7 integration or API,” Gregory explains. “That goes to HC1, and then those that where that doesn’t pencil out, those go to Shadowbox.”
This isn’t channel partnership or geographic territory division. It’s market segmentation based on integration economics profiles. Structured, predictable integrations where the ROI of custom development pencils out go to HC1’s traditional approach. Rapid deployments to fragmented provider networks where traditional integration economics break down go to Shadowbox.
Combined, they address use cases neither could serve independently. “Other competitors of ours, if you will, in our marketplace can’t offer what we’re offering as a combined thing,” Gregory notes.
The partnership also solves the credibility problem. HC1’s existing health system relationships provide access and validation that Shadowbox couldn’t generate independently at their stage.
Regulatory Positioning as Competitive Moat
Gregory’s background as a congressional staffer on Capitol Hill became an unexpected source of competitive advantage. He’s engaged with members of Congress, relevant committees, and the administration regarding expansion of information blocking provisions in the 21st Century Cures Act.
More significantly, Shadowbox supported the Coalition for Innovative Lab Testing’s lawsuit that successfully blocked FDA regulation of lab-developed tests as medical devices.
“That shows that we aren’t in it just for our own technology, our own company, our own customer, our own revenue,” Gregory says. “We’re in it for the industry and we supported it.”
This creates customer loyalty that transcends typical vendor relationships. Shadowbox isn’t merely solving a technical integration problem—they’re protecting their customers’ business models at the regulatory level. In heavily regulated industries, policy expertise and advocacy create defensibility that technology alone cannot provide.
The principle extends beyond healthcare. In any regulated market, founders with policy fluency or advisors who can influence regulatory outcomes create moats that competitors focused purely on product cannot replicate.
Where They Stand
Today, Shadowbox processes thousands of transactions daily across thousands of users. Gregory estimates they’re at 25-30% technology maturity but only 0.5% market penetration.
The vision: “Shadowbox will become the enterprise browser of choice for healthcare, meaning every single desktop laptop has a Shadowbox on it.” At scale, any healthcare provider could instantly integrate with any vendor or service through the Shadowbox browser without custom integration work.
The path from desperate labs to enterprise healthcare browser required unconventional decisions at each inflection point. Target segments others systematically avoid. Build partnership infrastructure before you have negotiating leverage. Use early segments as technology beachheads rather than final destinations. Partner with competitors when you address different use case economics within the same category. Deploy policy expertise as competitive moat in regulated markets.
These strategies don’t appear in standard B2B playbooks because they’re predicated on specific market conditions: broken unit economics creating adoption windows, slow-moving incumbents creating partnership opportunities, and regulatory complexity creating defensibility beyond product. But for founders facing similar constraints, Shadowbox’s path demonstrates how the segments and strategies that appear least attractive often provide the fastest route to validating technology that can eventually capture significantly larger markets.
Recommended Founder
Interviews
Ignacio Medrano
Founder & CMO of Savana
Ignacio Medrano, Founder & CMO of Savana: $44M Raised to Transform Healthcare Intelligence Through AI
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
Veer Gidwaney
CEO & Founder of Ansel Health
Veer Gidwaney, CEO & Founder of Ansel Health: $50 Million Raised to Transform Supplemental Health Insurance
Mike Desjadon
CEO of Anomaly
Why Anomaly avoids annual curiosity revenue (ACR) — and you probably should to | Mike Desjadon ($30M Raised)
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
Ty Allen
CEO of SocialClimb
Ty Allen, CEO of SocialClimb: $12 Million Raised to Power the Future of Healthcare Marketing
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
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
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
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
Omer Maman
VP of Marketing of Healthee
Why AI Should Enhance, Not Replace Your Marketing Team
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
Kevin Flyangolts
CEO and Founder of Aclid
Kevin Flyangolts, CEO & Founder of Aclid: $4 Million Raised to Build the Future of Biosecurity
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
Vicky Demas
CEO of Identifeye Health
Vicky Demas, CEO of identifeye HEALTH: $90 Million Raised to Power the Future of Retinal Imaging
Daniel Lambert
CEO of PathologyWatch
Daniel Lambert, CEO of PathologyWatch: Over $50 Million Raised to Build the Future of Digital Pathology
Dilpreet Sahota
CEO of Trek Health
Dilpreet Sahota, CEO of Trek Health: $3 Million Raised to Help Mental Health Providers Accept Insurance
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
Michael Passanante
Senior Vice President of Marketing and Communications of Capital Rx
How to Build 18-Month Attribution Models That Actually Work
Verena Gerhardus
Director of Growth of Nelly Solutions
How Nelly Grew 3X Through Meta Ads in Health Tech
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
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
Corey Washington
Senior Marketing Manager of Amenities Health
Humanizing Healthcare Tech: Marketing Lessons from Amenities
Joe Gagnon
CEO of 1upHealth
Joe Gagnon, CEO at 1upHealth: Over $75 Million Raised to Build the Future of Healthcare Data
Jennifer Bittinger
President and Founder of Narrativa
How Narrativa leveraged COVID-19 as a market catalyst to accelerate AI adoption in pharma | Jennifer Bittinger ($2.4M Raised)
Kristen Valdes
CEO & Founder of B.well
Kristen Valdes, CEO & Founder of B.well: $100 Million Raised to Reimagine the Healthcare Experience
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
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
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)
Amy Brown
CEO and Founder of Authenticx
Amy Brown, CEO and Founder of Authenticx: $28 Million Raised to Build the Future of Listening AI
Amar Kendale
President and Co-Founder of Homeward
Amar Kendale, President & Co-Founder of Homeward: $70 Million Raised to Transform Rural Healthcare Through Technology
Austin McChord
CEO of Casana
Austin McChord, CEO of Casana: Over $46 Million Raised to Create the Future of In-Home Health Monitoring
Senan Ebrahim
CEO & Founder of Delfina
Senan Ebrahim, CEO & Founder of Delfina: $10 Million Raised to Build the Future of Intelligent Pregnancy Care
Jocelyn Nowak
Marketing & Sales Enablement Lead of FIGUR8
Integrity-Driven Marketing: FIGUR8’s Path to 3,000+ Clinics
Brad Kittredge
CEO & Co-Founder of Brightside
Brad Kittredge, CEO & Co-Founder of Brightside: $150 Million Raised to Build the Future of Mental Healthcare
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
Michael Chang
Mastering Market Fit in AI: Insights from Michael Chang, Director of Marketing at ArteraAI
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)
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
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
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
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
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
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
Mark Lehmkuhle
CEO & Founder of Epitel
Mark Lehmkuhle, CEO & Founder of Epitel: $20 Million Raised to Build the Future of Brain Health Monitoring
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
Khaled Boukadoum
Founder of Torch Dental
Khaled Boukadoum, Founder of Torch Dental: $49.5 Million Raised to Transform Dental Supply Management Through Digital Innovation
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
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
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
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
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
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
David King Lassman
Founder of GigXR
David King Lassman, Founder of GigXR: $7 Million Raised to Bring Immersive Learning to Healthcare
Alexandra Ferraro
Head of Marketing of Intelligencia AI
Beyond Perfect: Healthcare Tech Marketing That Drives Real Revenue
Brett Kleger
CEO of Datacubed Health
Brett Kleger, CEO of Datacubed Health: $43 Million Raised to Revolutionize Clinical Trial Data Collection
Teodor Grantcharov
Founder of Surgical Safety Technologies Inc.
How Surgical Safety Technologies targeted the most challenging customers first (massive hospitals) | Teodor Grantcharov
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
Matt Renfro
Co-Founder & CEO of Lynx
Matt Renfro, CEO of Lynx: $17.5 Million raised to Bring Modern Fintech to Healthcare
Nick Soman
CEO & Founder of Decent
Nick Soman, CEO & Founder of Decent: $43 Million Raised to Build the Future of Direct Primary Care
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
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
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
Armon Sharei
CEO & Founder of Portal
Armon Sharei, CEO & Founder of Portal: $5 Million Raised to Power the Future of Cell Engineering
Todd Zion
Founder of Akston Biosciences
Todd Zion, Founder of Akston Biosciences: From a $500M Exit to Pioneering Biotech Innovation in Pet Health
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
Thomas Knox
CEO & Founder of VitVio
Thomas Knox, CEO & Founder of VitVio: $10 Million Raised to Transform Surgical Operations Through AI-Powered Automation
Danny Freed
CEO & Founder of Blueprint
Danny Freed, CEO & Founder of Blueprint: $13.7 Million Raised to Build the Future of Therapist Enablement
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
Marshall Darr
CEO & Co-Founder of StretchDollar
How StretchDollar drives leads from LLM search | Marshall Darr
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