Joubin Mirzadegan had a good gig. Partner at Kleiner Perkins, helping enterprise software companies grow, sitting in on board meetings where the real decisions get made. But somewhere between deal reviews and pitch decks, he kept bumping into the same irritating reality: the software his portfolio companies used to generate sales quotes was, as he'd later put it, "architecturally broken."
So he walked away from the VC job to build a replacement himself. Which is either brave or slightly mad, depending on how you feel about configure-price-quote software.
In May 2026, Mirzadegan's startup, Roadrunner, emerged from stealth mode with a newly available AI-native quoting platform and $27 million in venture backing split across two rounds. Kleiner Perkins led a $5.2 million seed, and Founders Fund came in for $22 million more in a Series A. Trae Stephens from Founders Fund took a board seat.
The pitch? Tear down the decades-old configure-price-quote category and rebuild it for companies selling consumption-based pricing, usage tiers, and the kind of Byzantine product bundles that make RevOps teams reach for spreadsheets at 11 p.m.
Roadrunner calls its approach "PQA"—Prompt, Quote, Approve. Natural language in, finished quote out. No dropdown menus, no configuration hell.
Whether the world needs another enterprise software company promising to fix a category that's "broken" is a fair question. Whether this one can actually displace incumbents like Salesforce CPQ and Oracle is another. But Roadrunner has something most challengers don't: a founder who spent years on the other side of the table, signing the checks for tools he's now trying to replace.
CPQ's Messy Middle Age
Configure-price-quote software isn't new. The category's been around since the 1990s, when enterprise sales meant configuring physical products—servers, telecom equipment, manufacturing components—and pricing was relatively static. Annual contracts. Fixed SKUs. Straightforward discounting.
Then the software industry moved to the cloud, and pricing got complicated. Fast.
Today's B2B companies sell usage-based models that fluctuate month to month. They bundle SaaS seats with API call limits and support tiers. They offer hybrid pricing where some features cost per user and others scale with consumption. Legacy CPQ tools, built for a simpler era, struggle.
Sales cycles drag. Approvals bottleneck. RevOps teams maintain shadow systems—spreadsheets, scripts, custom integrations—alongside their official CPQ platform because the official one can't keep up.
Grand View Research pegged the global CPQ software market at $3.46 billion in 2025, projecting growth to $10.89 billion by 2033. It's a crowded space. Salesforce, Oracle, Conga, PROS—the incumbents dominate, layering on features and AI-assisted tools but never quite escaping the architectural decisions made when Clinton was president.
Mamoon Hamid, the Kleiner Perkins partner who led Roadrunner's seed round, framed the problem in a company blog post: "CPQ is an architecture problem, not just a configuration problem."
In other words, you can't patch your way out of bad foundations.
What "Prompt, Quote, Approve" Actually Means
Here's how Roadrunner's platform works, at least in theory.
A sales rep doesn't log into a configuration interface and navigate nested dropdown menus. Instead, they describe what the customer needs in plain language: "10,000 API calls per month, 99.9% uptime SLA, premium support included."
The system interprets that prompt, applies pricing logic, checks approval workflows, and generates a quote. The platform integrates with CRM and billing systems. It's built on a data model designed for consumption pricing from the start, not retrofitted onto legacy infrastructure.
The difference matters when pricing gets genuinely complex. Imagine a SaaS company with seat-based pricing, usage overages that kick in at different thresholds depending on the product line, volume discounts that vary by region, and custom contract terms for enterprise deals. Traditional CPQ requires extensive—sometimes painful—configuration to handle that. Roadrunner treats it as an AI reasoning problem.
Fortune reported that Roadrunner closed a seven-figure deal within three months of early prototyping. That's an unusually fast timeline for enterprise infrastructure software, though the story doesn't specify whether that was an outlier or a signal of broader traction.
The Incubation Bet
Mirzadegan didn't stumble into this. Before joining Kleiner Perkins in 2019, he spent years in sales leadership at security and cloud infrastructure startups. He ran sales at Evident.io before Palo Alto Networks acquired it. He held roles at Bracket Computing before VMware snapped that up too. And he scaled Palo Alto Networks' cloud business from $2 million to over $50 million in annual recurring revenue in four quarters, which is the kind of trajectory that gets you noticed in Silicon Valley.
His co-founders bring AI chops. Ajay Natarajan, the chief product officer, started at Caltech at 16, worked at NASA, and co-founded Athena, an AI-powered college admissions platform reportedly used by around 2% of U.S. college-bound students before its acquisition in 2025. Eugene Shao, the CTO, also co-founded Athena after engineering stints at Citadel and Meta, bringing deep technical expertise from his work at leading tech companies. (Whether astronauts need quote software is unclear.)
The timing here is deliberate. Roadrunner was incubated inside Kleiner Perkins—the firm's first incubation project since Glean, which recently hit a $4.6 billion valuation. That incubation model gave Mirzadegan runway to validate the thesis before spinning out as an independent company in 2025.
By the time Roadrunner announced general availability, Founders Fund was ready to lead the Series A. Stephens, in the press release, said what VCs usually say: "Revenue infrastructure hasn't kept pace with modern pricing models. Roadrunner is fixing that with an AI-first approach."
The Long Game
The $27 million will go toward scaling the team, deepening enterprise partnerships, and expanding beyond quoting into the full quote-to-cash workflow—pricing strategy, approvals, billing, revenue recognition. That's a big scope. It also puts Roadrunner on a collision course with not just CPQ vendors but billing platforms, revenue operations tools, and ERP systems.
The company is based in San Francisco and is actively hiring. It hasn't publicly named customers yet, though its website mentions the platform was "co-developed with enterprises" and includes a testimonial from an unnamed CIO. That's typical for early-stage enterprise startups—get design partners under NDA, iterate fast, announce customer wins later.
The market opportunity looks real. North America held about 37% of the global CPQ market share in 2025, according to Grand View Research, and demand is climbing as more companies shift to usage-based and hybrid pricing models. Recent M&A activity—like DealHub's acquisition of subscription billing platform Subskribe in late 2025—suggests buyers want unified quote-to-revenue stacks, not point solutions stitched together.
Still, displacing entrenched incumbents is hard. Salesforce CPQ has deep CRM integration. Oracle has enterprise accounts locked in. And sales teams, for all their complaints about clunky tools, are notoriously resistant to switching once a workflow is embedded.
Roadrunner has capital, a clear thesis, and investors with track records in enterprise infrastructure. It also has a CEO who spent years using the very tools he's now trying to obsolete. Whether that insider knowledge translates to market traction is the question every early-stage enterprise software company eventually has to answer.
For now, the bet is that quote software doesn't need incremental improvement. It needs to be rebuilt from scratch, with AI at the center and modern pricing assumptions baked in. Whether enterprises agree—and whether they'll rip out existing systems to find out—is a story that'll take a few years to resolve.
