Over the past decade, software has reshaped nearly every facet of business, evolving from a tool into the engine of modern enterprise. As companies across industries accelerate their digital transformation, the most successful venture capital firms aren’t simply chasing the next big app – they are building systems to identify and back the foundational technologies of tomorrow.
At the forefront of this evolution is 645 Ventures, co-founded by Aaron Holiday, a software engineer turned investor, and Nnamdi Okike, a Harvard-educated tech entrepreneur and former Insight Partners executive. With more than $550 million in assets under management and 68 active portfolio companies, 645 Ventures is proving that a systematized, data-informed approach to investing can deliver powerful results. “We back transformational software companies,” says Holiday. “Especially those that help businesses operate faster, smarter, and more efficiently.”
From Building to Investing in Algorithms
Holiday’s journey into venture capital was far from traditional. He began his career at Goldman Sachs, where he built high-frequency trading algorithms for the equities desk. He later developed one of the first digital trading platforms for foreign exchange options at GFI Group, replacing a manual, voice-driven process with software. “I’m a software engineer by training,” he says. “And I always believed that software could make even the business of venture capital more intelligent and scalable.”
That conviction would form the basis of 645 Ventures. In the early 2010s, Holiday was working at an early-stage VC fund when he was introduced to Okike, who had spent years at Insight Partners. Nnamdi had started to think about leaving Insight to bring outbound deal sourcing to the seed stage. A mutual founder connected them. “She said, ‘You two are saying the same thing – you should meet.’” They did – and quickly realized they were aligned not only in vision but in timing.
The duo saw two major structural shifts happening in early stage venture. First, startups were being launched at an unprecedented rate, overwhelming the human networks that traditional funds relied on for sourcing. “There were so many companies getting started that the traditional boutique seed fund was starting to get overwhelmed by the deal volume,” Holiday says.
Second, the way investors discovered companies were beginning to shift from personal connections to digital signals. “Historically, you learned about startups through personal networks. But by then, data trails were forming. We believed you could build software that scoured the Internet, assembled that information, and surfaced companies your network couldn’t show you.”
A Digital Backbone
That belief gave rise to Voyager, 645’s proprietary software platform—and a key part of what makes the firm stand out. Voyager serves as the firm’s internal brain, aggregating and analyzing data from founder conversations, market research, and third-party sources.
“Everything our team does with companies gets recorded and put into the system. We turn unstructured data into structured data, which gives us analytics on things like real-time entry prices by stage.”
Aaron Holiday, Co-Founder and Managing Partner
One of Voyager’s standout features is called Candidates—a discovery engine that flags high-potential companies the firm hasn’t yet seen. That’s how 645 discovered Panther Labs, a cybersecurity platform launched by a former Airbnb senior security architect. The company went on to raise Series A and Series B rounds in late 2021 at a significantly higher valuation.
A Thematic Approach to Transformational Software
645 Ventures’ core focus is enterprise software—specifically SaaS, developer tools, and infrastructure platforms that help companies build better, faster, and more reliably. However, within that broad category, the firm has developed unique theses to guide its strategy.
One such theme is Citizen Professional, an investment thesis that has guided the firm for nearly a decade. “The idea is to invest in software that reduces the complexity of something that usually requires a trained expert,” Holiday explains. Long before the rise of AI, 645 was backing platforms that made specialized work accessible to non-technical users. A prime example is Iterable, an email marketing automation tool.
Though enterprise is its foundation, the firm has also made select bets in consumer –particularly when digital innovation is core to the model. One success story is Resident, a direct-to-consumer furniture brand that was acquired by Ashley Furniture for $1 billion in 2023.
The Next Big Thing
Looking ahead, Holiday sees opportunities in emerging sectors where enterprise needs are evolving rapidly. One is defense technology, a category 645 has quietly backed for years and is now gaining mainstream interest. “The primes – large defense contractors – are overwhelmed,” Holiday says. “They can’t innovate fast enough. The government is looking to startups to fill that gap.”
Another is causal AI, a form of artificial intelligence that focuses on identifying root causes rather than generating content. “Unlike generative AI, which is predictive and often hallucinates, causal AI can tell you why something happened,” Holiday explains. One 645 portfolio company, Causely, is using causal AI to improve software observability – an essential function in today’s complex tech stacks.
And then there’s what Holiday calls “Ready for Primetime” AI – enterprise-grade generative AI applications that have moved beyond experimentation. One promising area is AI-powered call center solutions, which are already showing measurable gains in efficiency and customer experience.
After 10 years of building its software platform and refining its investment strategy, 645 Ventures has created a flywheel effect – each year strengthening its systems, sharpening its insights, and widening its competitive edge. Through Voyager, the firm is sourcing and evaluating companies more intelligently while helping founders scale faster. 645 is also playing its part in driving venture capital’s evolution into a more precise, software-driven industry. “We’re not just investing in software,” Holiday says. “We’re using it to transform how venture itself is done.”