In venture capital, it’s common for investors to categorize themselves—by stage, sector, or specialization—so that founders and co-investors know when to think of them for a deal. For me, that simple categorization has never cleanly fit.
Over the last five years in venture, I’ve found myself bucketed into commerce, vertical SaaS, marketplaces/procurement, and logistics. Dealmaking across this many categories may make it seem to some like I’ve lacked focus. In reality, there’s a very clear throughline in all the deals that I pursue.
My operating background has always centered on improving the commerce value chain. If you look at some of the most transformative software companies of the past few decades—Stripe, Shopify, Square—they weren’t just fintech or e-commerce infrastructure; they were fundamentally rethinking how we buy, sell, and exchange goods, services, and experiences.
It’s not just about digitizing workflows or increasing margin; it’s about making transactions more intuitive, faster, more accessible, and ultimately better for both the seller and the end user.
That belief is reflected across many of the deals I’ve helped champion in the Headline portfolio, like:
- Verse Medical: improves hospital discharge workflows—reducing readmission, improving patient outcomes, and streamlining coordination between hospitals and in-home care providers.
- Nivoda: helps jewelers supply better stones, more quickly at better prices and gives jewelers tools to better serve their end customers.
- Motion: helps brands reach customers more effectively—improving targeting, creative, and outcomes, so customers see ads they actually want and brands grow efficiently.
- Heidi Health: helps doctors focus on care by removing the operational burden allowing for less fatigue and burnout giving them more time with patients.
- Heard: takes the complexity out of finances for therapists so they can prioritize patient time and care.
- Atlys: reshapes the visa process for travelers and governments alike—offering a seamless consumer experience that removes friction and guesswork and tools for governments to improve workflows.
In each of these cases, aligning incentives across stakeholders—buyer and seller, provider and patient, consumer and brand—creates step-change improvements for all parties. The best products don’t just digitize analog tasks; they make the entire exchange better.
Why AI Changes the Game
We’re at a unique moment in time for venture. Today, what excites me and many of my colleagues most is that AI is making tractable what used to feel impossible. Suddenly, industries that seemed too messy, fragmented, or slow-moving are open to software. In healthcare, we’re seeing the cost and complexity of insurance verification drop dramatically. In logistics, agentic interfaces are solving longstanding connectivity issues between TMS platforms and end carriers. In biotech, the time from drug discovery to commercialization is compressing.
We’re entering an era where nearly every interaction in commerce can be automated, optimized, and personalized with AI, whether that’s ordering materials, billing a patient, or booking international travel. Every interaction, across industries, can better align with its stakeholders. And the implications for antiquated industries and deskless workforces—often the last to innovate—are profound.
The Evolution of Software: Verticalization → Intelligence
Over the past three decades, we’ve watched the software stack evolve from general-purpose to vertical-specific. Salesforce, Intuit, and ServiceNow paved the way, and in their wake came Veeva, ServiceTitan, Procore, Benchling, AppFolio, and Shopify—each defining a new category by solving problems deeply and specifically.
Now, we’re seeing the next shift: intelligence-first systems that don’t just serve workflows but actually think alongside their users. The most compelling companies today are embedding AI into the core of their products—not as a feature, but as a native capability. And as software becomes cheaper to deploy, the differentiators become:
- Specificity – Deep understanding of the industry problem
- Distribution – Smart, scalable go-to-market motion
- Community – Strong alignment with end-user identity and habit
In vertical software, these principles guide where we’re investing next.
AI Infrastructure for the Real Economy
Some of the sectors we’re most excited about are ones that have been historically under-digitized, often due to legacy processes or complex workflows. And even more pressing is that many of these industries are struggling with labor shortages. We see opportunity across:
- Supply Chain & Logistics: Companies like Happy Robot, Auba, Drumkit, Rectangle and Importal are helping brokers, carriers, and shippers reduce margin pressure by eliminating manual steps and increasing visibility.
- Manufacturing: Companies like Squint, Endeavor, Complement are using AI to drive increased productivity in manufacturing by helping knowledge transfer, training and identifying the highest impact improvements on any floor.
- Government: Tools like Hyper, Polimorphic and Govwell are helping local and state agencies triage requests, manage permits, and serve constituents with fewer resources.
- Science & Biotech: Platforms like Mithril and Potato are making early-stage discovery and R&D programmatic and less reliant on trial and error and players like Bluenote and Weave are making the drafting and approval process more seamless.
- Network Engineering: Layer9 is automating tasks for Managed Service Providers (MSPs) and Internet Service Providers (ISPs), bringing observability and efficiency to systems-level work.
- Dental Billing & Verification: Lassie, Stratus, and Daydream are helping practices stay insurance-friendly without operational drag.
- Construction: Ichi and Provision are using AI to help contractors stay compliant and organized, identifying clear risks sooner and acting as an extended member of the team.
- Retail Ops: Companies like Augmodo and Treator helping brands and retailers keep shelves stocked and increase sell-through for retailers and brands.
New Markets Created by AI
Beyond unlocking old industries, AI is also spawning entirely new categories that we’ve been obsessively tracking. As AI-native tooling becomes embedded in the economy, adjacent infrastructure layers are being built—from physical capacity to contextual distribution:
- Data Centers & Cooling: Companies like CentralAxis and ClearCurrent are powering the next wave of AI compute.
- Nuclear Platforms: Everstar and Atomic Canyon are making clean, high-density energy more viable.
- LLM Visibility & Optimization: Profound, Evertune, and Bluefish are helping brands and tools appear contextually in LLM environments.
- Next gen ad networks and agent to agent transactions: companies like Tollbit, Kontext, and Koah are starting to show how the future advertising and commerce transactions may look.
Closing Thoughts
As we move into this next era, the companies that will matter most are the ones that combine intelligence, infrastructure, and alignment across users. They’re not just building better software—they’re enabling a new way of transacting. As AI continues to lower barriers to entry, automate complexity, and reveal new surfaces for innovation, we’re more excited than ever to back the next generation of founders shaping how the real economy runs.
If you’re building in any of these spaces, please email taylor@headline.com or jerry@headline.com to chat!
Headline investor Jerry Fung contributed to this piece.