Verissimo Monthly - May 2026
What the past tells us about the future of enterprise software
Thoughts on Investing and Starting Up
What Does Enterprise Software Become?
I spent an hour this week chatting with Roy Rubin, and I haven’t stopped thinking about one question since.
Roy built Magento out of a freelance shop while he was still a student. He gave the software away for free, watched his customers fund his growth, and eventually sold the company to eBay. He now invests in enterprise companies at the earliest stages. So when he talks about how this business works, he’s not theorizing, he’s describing a thing he lived through from the inside.
The question we kept circling was simple to ask and hard to answer. What is enterprise software, actually, anymore. And the more we talked, the more I realized the answer lives in a part of the industry most people stopped paying attention to a long time ago.
The part of the story nobody tells
When Roy released Magento, he assumed the business would be services and support. His intuition, after years of picking up the phone in the middle of the night for e-commerce customers, was that mission-critical software means people want a vendor on the other end of the line. He was right about the need, wrong about who would fill it. The systems integrators who downloaded his open-source product turned out to be better at support than he was, and overnight he had an ecosystem servicing his customers for him.
So he leaned into the product business. He intentionally left holes in the product, gaps for third parties to come in, plug, customize, and ultimately own the customer relationship. The product company built the core. The integrators did the work.
This was not a Magento quirk. This is the whole history of enterprise software. Oracle, SAP, Salesforce, every large platform got distributed, implemented, and made to actually function inside real organizations by a vast layer of value-added resellers and systems integrators sitting on top of it. While valuable, building the software was the easy part. Making it work was the business.
We tend to forget this because the SIs and VARs were never the glamorous companies. Nobody grew up wanting to work at one. They trade at half a turn of revenue while the platform vendors trade at ten times or twenty. But they were always there, and they were always essential, because software has always been a bunch of screens on top of a database that somebody still has to install, configure, and teach people to use.
The premium was a wedge
For about twenty years, the most valuable software companies shared two traits. They were a system of record, and they encoded a work methodology. A dollar of revenue at a company that was both was worth more than a dollar of revenue at a company that was only one. Salesforce is the obvious case. While it is a fairly straightforward database with screens on top, it also defined the modern CRM. It became the way an entire profession does its job, to the point that "Salesforce admin" is a job title.
That second trait, the methodology, is what makes revenue sticky. It is what lets incumbents survive on friction alone. Moving off a deeply embedded workflow was so painful that the new thing had to be not a little better but dramatically better to justify the switch. The friction is the moat.
What’s changing now with AI is that the friction is collapsing. Migrating from one system to the next used to be a year-long project. With APIs, MCPs, and agents that can run a migration cleanly in a week, the switching cost that protected a generation of incumbents is dropping toward zero. The wedge that the SIs drove in, and that the platforms turned into pricing power, is getting thinner.
But what comes out of this may not be what you first assume.
The labs just answered the question, sort of
Here is the part that made me sit up. For the entire history of this industry, the model was the platform vendor builds the product, and a separate ecosystem of integrators does the services. The two stayed separate. Service revenue was even vilified on public company income statements, low-margin, non-recurring, the stuff you wanted off your S-1.
This month, that separation broke in the most visible way possible. Anthropic launched an enterprise services firm with Blackstone, Hellman & Friedman, and Goldman Sachs. Days later, OpenAI launched its own majority-owned deployment company and bought an applied AI firm to staff it. Both are copying Palantir’s forward-deployed-engineer model, putting their own people on-site inside customers to make the technology actually work.
In other words, the platform vendors looked at the services layer that every prior generation handed to an ecosystem, and decided to keep it. They are betting that the bottleneck in this cycle is not the model, it’s implementation, and that whoever owns implementation owns the customer.
Roy left holes in his product so an ecosystem would form. The labs are trying to do the exact opposite, pulling the work back in house before an ecosystem can form at all. Same structural question, opposite answer, and it’s genuinely unclear who will be right.
So what does it become
If the model layer is a commodity, and the switching cost between models is zero, and the platform vendors are absorbing the services layer themselves, then the comfortable distinctions we’ve relied on for two decades stop holding. A lot of what’s being sold as vertical AI software turns out, on inspection, to be a system integrator wearing a SaaS costume. The startups discovering this are learning they have to charge like Accenture to deliver like Oracle, because customers need so much help that the product alone was never the thing being bought.
That doesn’t mean the startups lose. It means the thing that wins looks different from what won last cycle. Not a thin wrapper on a model, but a genuinely deep workflow that the model providers won’t bother to build and the incumbents are too slow to reach. The value moves back toward the part everyone undervalued, the work of making the software actually fit the business, and away from the part everyone overvalued, the interface on top of the database.
Which is to say the future of enterprise software might look a lot like its past. Customers funding growth. Services and solutions as the real business. Integrators, by whatever name, capturing the value. The picks and shovels outlasting the gold rush, the way they always do.
The full conversation with Roy Rubin is on the Very True podcast.
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Portfolio Highlights
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Certa gives companies one place to vet and monitor the outside vendors, suppliers, and partners they rely on. The platform uses AI to automate the full relationship, from onboarding and background checks to ongoing risk and compliance monitoring, a process that has long been slow and manual for most companies. Customers like Honeywell, Uber, and Box use Certa to onboard new partners up to three times faster, and it was recently named a Leader in the first ever Gartner Magic Quadrant for third party risk management tools.
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Verissimo Ventures is a Pre-seed and Seed Venture Fund based in Israel and the US. We take a fundamentals-driven approach to early-stage investing. We work closely with founders to help them build the strongest, most fundamentally sound businesses with potential for explosive growth and a meaningful impact on the market.
We were founded in 2020 and are currently investing out of our third fund.