Most CFOs have invested heavily in the technology that governs how their companies spend money. The software governing everything that happens after a deal is signed, how they invoice and collect, until recently, has been patchwork: held together with spreadsheets, professional services, and institutional patience. Rebecca Schwartz, Co-Founder of Tabs, is building the platform she believes will finally change that.
Tabs is an AI-native revenue platform built to own the entire revenue lifecycle across billing, collections, revrec, reporting, and audit. Tabs takes the unstructured complexity of B2B commercial relationships and replaces the manual workflows that surround them with AI agents that can invoice accurately, collect faster, and recognize revenue without human intervention. The company has grown from 5x and from 40 people to nearly 200 during the period Evan Osheroff, Managing Director of Software Investment Banking at Jefferies, has been following it, and it counts itself among a cohort of businesses built for the AI era from day one rather than retrofitted to it.
Schwartz sat down with Osheroff to discuss what makes contract-to-cash such a hard problem, how Tabs is positioning itself against both legacy incumbents and well-capitalized new entrants, and what the long-term vision looks like for a business with Stripe in its sights.
The Problem Nobody Solved
The AR process has always been resource intensive. More than half the headcount on a typical accounting team, in Schwartz’s telling, spends most of its time on billing, revenue and AR-related work. And yet, as Osheroff observed, the generations of software that transformed AP, payroll, spend management, and financial planning largely left the billing and revenue side of the ledger untouched. “Tech-forward CFOs who had invested in great platforms for everything else would describe their contract-to-cash process, and it was almost always professional services and spreadsheets held together by duct tape,” Schwartz said.
The problem, she argues, is fundamentally one of unstructured data. Legacy billing automation was built on the assumption that structured data would be input precisely and maintained rigorously: that a sales team would correctly capture every deal in the CRM, that it would match the executed contract, that amendments and redlines would flow cleanly downstream. In practice, none of that holds. “The contract gets redlined, the pricing model evolves, the CRM is never up to date,” she said. “You’re trusting a lot of people who don’t necessarily have a ton of rigor around what they’re putting in those dropdowns.”
AI’s ability to interpret unstructured data alongside structured data is what makes the problem more tractable. Tabs ingests contracts, amendments, purchase orders, and even email exchanges to build a commercial graph of each customer relationship, which it then uses to power the agents that handle invoicing, collections, and revenue recognition. “There might be a side email that says: ‘I know the contract says August 1st, but it’s going to be August 15th,'” Schwartz said. “All of that is an awesome problem for AI to tackle.”
Where Tabs Sits in a Crowded Market
The recent wave of M&A in the billing and metering space (for example Stripe’s acquisition of Metronome, Adyen’s purchase of Orb, and Salesforce’s acquisition of Meter), has consolidated a significant amount of capital and distribution around usage metering. Schwartz is sanguine about it. “Companies like Metronome and Orb went very deep on product analytics and the aggregation of billable events,” she said. “But that is not the end of the job.”
What those platforms do well stops, in her view, at the point where the invoice is generated. The work of sending it, collecting on it, receiving payment, recognizing revenue, and syncing to the ERP (the accounting jobs to be done) remains largely unaddressed. “They never touched revenue recognition,” she said. “And if you’re building technology for product and engineering, you’re probably not worried about ASC 606. But the accountants always had to do those jobs anyway.”
The other competitive dynamic Schwartz highlighted is arguably more significant than the well-capitalized fintechs: the deep ecosystem of custom software and professional services that has historically surrounded ERP systems like NetSuite. For many finance teams, the way they handled contract-to-cash was to hire consultants to stitch their CRM and ERP together in brittle, expensive ways. Every time their business model changed, they had to do it again. “That model stops working in a world where your business model is going to change all the time because AI monetization is still evolving,” she said.
Building for the AI Era From Day One
Schwartz is precise about what it means to be AI-native, and equally precise about what it doesn’t. The large ERPs and legacy SaaS platforms have begun adding AI features, but she sees those as fundamentally different from what Tabs has built. “There’s an AI widget sitting on top where you can have some sort of chatbot experience,” she said. “What we’re trying to do is think in an AI-centric way from the beginning: how we build software, the AI agents we’re building, and how we think about data.”
That data architecture is what Schwartz calls the commercial graph: a continuously updated representation of the financial relationship between Tabs’ customers and their own clients, built specifically to serve as context for all agents on Tabs. “The agents are only going to be as effective as the context you serve them up with,” she said. “We’ve really anchored our strategy on mastering that graph.”
On the question of whether foundation models will eventually replicate what Tabs does, she is direct. “The level of specificity and focus that we’ve brought to this market is not easily replicable,” she said, pointing to the sensitivity of the workflows involved. Writing directly into an ERP, managing revenue recognition data that auditors review, communicating with customers about payment, these are not processes that finance teams will hand off to a general-purpose model. “People still want suitable controls,” she said. “And accounting is at the top of the list.”
The Road Ahead
Tabs is moving upmarket, which Schwartz describes as both a product challenge and an opportunity. Serving larger, more complex organizations, ultimately including publicly traded companies, requires enterprise-grade security, compliance infrastructure, approval workflows, and international capability. “That upmarket push requires a ton of product development to ensure we’re truly enterprise ready,” she said. “But it also propels us in terms of average contract value.”
The fintech layer is coming too. Tabs already integrates with banking partners to track when cash hits the account and apply it automatically against open transactions. Schwartz sees that deepening over time. The company’s agnosticism on payment methods (ACH, wire, credit card, stablecoin) gives it the flexibility to follow its customers wherever the market moves. “Once you hit cash, gross retention skyrockets,” Osheroff observed. “No one wants to swap out a cash process.” Schwartz agreed. The long-term vision is full ownership of the contract-to-cash and contract-to-audit lifecycle, with a fintech layer underneath and, eventually, AR agents talking directly to AP agents on the other side of the transaction.
Asked to name the company Tabs is going after, Schwartz did not hesitate: Stripe. The ambition is not modest, but neither is the problem she is trying to solve.
