Howdy! Caroline here- I’m thrilled to be the latest addition to the Cowboy team. Before this, I spent over a decade working with software companies, from ideation-phase startups to Fortune 500 institutions. Most recently I was at Construct Capital, investing in early stage tech companies transforming foundational industries. Before that, I was building and investing in AI companies with Andrew Ng. 

We are hitting the ground running in 2025 to find and work with incredible trailblazers, changemakers, and legends in the making. As we kick-off the new year, I wanted to share a few areas we’re particularly excited to invest behind:

‍

‍Vertical SaaS Transformation 

As AI infrastructure advances rapidly, we continue to see opportunities in vertical, AI-powered software applications that embed cutting-edge technology into specific, everyday workflows that benefit from domain specific UI, data, and models. 

‍Modern alternatives replacing aging incumbents: We're witnessing a rare window for disruption of entrenched incumbents with massive market share but terrible NPS scores. Why? The emergence of AI is catalyzing enterprises to reassess their entire tech stacks for the first time in years or sometimes decades. Even long standing systems of record are on the chopping block, vulnerable to being ripped and replaced with AI native, modern alternatives. Of course overcoming industry or organizational inertia and risk aversion will never be easy and differentiation and defensibility will be even harder in the AI age. Ambitious startups will need a high value wedge and the product velocity to expand quickly, create innovative data loops, and establish themselves as a core user operating system or “system of intelligence”. We're particularly bullish on vertical opportunities in fintech, healthcare, and logistics - sectors where we've already placed some exciting bets (stay tuned for announcements!).

‍SaaS→ CoPilots →Agents: The initial wave of vertical co-pilots is showing early promise in augmenting human workers and driving efficiency. The best ones are also building greater user trust in the system and eliciting human input that becomes a net new dataset for continuous improvement. The real magic will come as agentic workflows become both more robust and trusted. For this future to be realized, we’ll also be looking for founders building the enabling infrastructures that will bring safety and security to the agentic future- from authentication and permissioning to non-human identity discovery and beyond. 

‍

AI for the “real” world 

We’re particularly keen to invest behind the decidedly unsexy, overlooked spaces that drive the economy forward. These sectors—like logistics, manufacturing & industrials, and healthcare—are operating with woefully outdated tech stacks. They are burdened with multiple siloed systems, unstructured and dirty data, and highly manual processes. Generative AI can not only incrementally improve processes here, but also create entirely new and previously impossible ways of working. Note: the future winners here may look different: think service-as-software businesses that use AI behind the scenes for radical efficiency gains; or companies building the entire stack from scratch vs selling into a highly fragmented, long tail of unsophisticated software buyers. There are several new models to explore. 

Two other areas I’m watching closely in “real world” AI:

‍Physics Defined AI: Physics-based AI combines the predictive power of machine learning with the reliability and precision of physics, enabling breakthroughs in fields like renewable energy, advanced manufacturing, drug discovery, and climate modeling. This approach delivers more accurate, interpretable, and trustworthy solutions, addressing the limitations of traditional “black-box” AI and catering to high stakes, real world problems. 

‍AI at the Edge: Devices are everywhere! Small model and compute advances are opening up the doors for on-device LLMs that can run locally, delivering everything from retrieval to processing to inference at the edge. On-device processing should deliver superior speed and response time with reduced costs and enhanced privacy. It’s particularly salient in Industrials where plummeting hardware costs has led to a boom in IoT, but connectivity and latency constraints as well as high cost for failures (think contamination of the food supply, disruption of the power grid, or even catastrophic events like explosions) have historically limited AI adoption in locations like factories and remote facilities.  More sophisticated edge solutions can help tackle these challenges. 

‍

Workforce of the Future 

We are in a period of enormous workforce upheaval and transformation. By 2050, close to a quarter of the US population will be 65+ (up from ~16% in 2020). We’re interested in startups that will help to define that new era- reckoning with not only the demographic forces but also the technological and social ones that are driving change here. These forces include: 

‍New Demands for Flexibility: The rise of the gig economy over the last 15 years has changed worker expectations. Flexibility is an increasingly important factor for workers (especially those in hourly or shift roles like healthcare, warehousing, food service and entertainment). Winning solutions will enable companies of all-sizes to better compete by streamlining workforce acquisition, retention, certification, scheduling, and on-going management.  

‍Rebuilding the industrial workforce: There is a projected five million worker shortfall expected in industrials by 2030. Increased pressure for reshoring production alongside proposed Trump administration tariffs and immigration policy changes may be further accelerants. New and better solutions to help attract, train, and retain talent in these spaces, as well as automation and augmentation products that will drive labor efficiencies, will all be critical. 

‍Robot Enablement: AI powered hardware and robotics are back in a big way. The gains in generative AI and autonomy are once again being integrated into the physical world- and beyond self-driving cars and mobility. Workers with multi-disciplinary skill-sets that bridge advanced SW and HW will be in high demand and new jobs will be created to build, work alongside, and maintain robots across use cases. 

If you are building, investing, or just brainstorming in these spaces- let’s talk! It’s never too early to reachout. Caroline@cowboy.vc

‍