Enterprise software has been stuck in time for decades. Too deeply embedded to replace, the same systems of record (SORs)—Salesforce, SAP, Oracle—have been the unshakable backbone of businesses.

But these platforms weren’t built to make work efficient; they were built simply to track it. They require years of customization, layers of bespoke code, and an army of consultants to function. The result? A spaghetti of legacy tech that companies are terrified to touch. Newer SaaS platforms couldn’t break through because the cost and pain of switching always outweighed the benefits.

That equation has just flipped. AI is here, and it’s ripping the old enterprise stack apart.

The Legacy Lock-In Problem

For years, the argument for SORs was simple: they were the single source of truth, a custom-built solution that enterprises couldn’t function without. They stored customer data, processed transactions, and tracked business activities.

The problem is they were built for an era where humans did all the work. While some SORs built automated workflows around the margins, most tasks were left for the human. These were systems where people had to manually input data, run processes, and jump between applications. That inefficiency didn’t matter because there wasn’t an alternative—until now.

Why AI Is the Breaking Point

AI won’t just make these systems better. It will change how SORs work entirely.

1. AI will obviate most manual workflows. For jobs that touch a SOR, a majority of the work is simple data extraction, manipulation, and entry. Today’s AI systems automate those tasks with ease. They will drive such dramatic operational efficiencies that if a company doesn’t adopt them, they will fall behind.
2. AI-first platforms will beat bolt-on features. AI systems need to be deeply integrated with data and systems to work effectively. Bolting them onto decades-old platforms will limit their capabilities and create implementation headaches. Companies will realize that the most effective platforms are the ones built ground-up for AI.
3. AI mitigates the “too expensive to switch” argument. For decades, businesses have stayed put because ripping out an SOR meant months (or years) of painful migration. AI changes that by auto-configuring new setups, mapping integrations, and making transitions simpler.

How Startups Take Down the Giants

What will this opportunity look like in practice? There are two paths:

1. Workflow-First (The Trojan Horse Approach)

Start by automating a high-friction workflow—something painful, manual, and critical. Sales teams, finance teams, HR teams — they’ve all built out cumbersome processes on top of their SORs. An AI-powered workflow tool can swap in for these and automate most of the work.

At first, the legacy system is still there. But over time, people stop logging into it and it becomes a generic backend database. At some point, companies realize: Why are we paying millions for this thing we barely use? That’s when they make the switch.

2. Full Replacement (The Hard but Inevitable Play)

Some categories—like ERP—only work if you own the whole stack. You can’t automate workflows in a fragmented system. You need full data control, deep integrations, and an AI-native foundation.

This is a big bet. It’s harder, takes longer, but the upside is generational and competition is fewer. Just like Figma didn’t win by layering on top of Photoshop—it built a fundamentally better, cloud-native editor—AI-first ERPs, CRMs, and financial systems will replace legacy players entirely. The startups that pull this off won’t just be new SaaS companies; they’ll be the next Salesforce.

This Isn’t a Theory—It’s Already Happening

We’ve seen early signals of what happens when AI collides with legacy business software.

For example, our portfolio company Doss is an AI-first adaptive ERP and data platform that can be easily configured and modified for any business workflow. Rather than allowing customers to simply modify UI or reports, Doss fundamentally makes it possible to change the data model, business logic, and application, all without third-party code. No matter the industry, implementations that would have taken a year can be completed in days to weeks.

The CRM space is also evolving rapidly. Today’s CRMs are designed primarily to track activity as a prospect moves through the sales funnel. With AI, they will turn into operational platforms where people manage AI agents to do automated prospecting, outreach, and account management. Attio, Clay, Rox, Day, and others are building for this future; some as workflow tools that operate existing systems, others replacing the CRM entirely.

Overhauling SORs Resets Enterprise Software

Markets like this don’t open up often. For years, the prevalence of incumbents made switching impossible and innovation incremental, but that time has passed.

The next decade will be defined by AI-first enterprise software that automates entire workflows and makes legacy SORs obsolete. Companies will either adopt or die.

For startups, this is a once-in-a-generation window — build now, or watch someone else do it — and for enterprises, it’s the right time to get ahead of the curve on implementation.