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Litigators, Meet Your AI Co-Pilot: How Callidus Is Quietly Rewiring the Legal Operating System

Nima Olumi by Nima Olumi
July 31, 2025

Justin McCallon Callidus Legal AI

When Justin McCallon launched Callidus Legal AI two years ago, he wasn’t chasing hype, he was engineering a fix for the deep, grinding inefficiencies he’d lived firsthand in the legal trenches.

McCallon, a former commercial restructuring attorney who later ran AT&T’s legal transformation and launched its first generative AI product at DIRECTV, knew firsthand that legal work wasn’t just inefficient. It was unscalable. “We saved $100 million a year at AT&T’s legal division through process overhaul,” he said. “But it wasn’t enough. I saw firsthand how AI could go further.”

So he built Callidus not as a chatbot, but as an AI operating system for litigators, complete with a proprietary case law engine, multi-step workflows, and agentic reasoning tools designed to enhance, not replace, the lawyer.

“Our goal isn’t to automate the lawyer out,” McCallon explains. “It’s to make them exponentially more effective.”

From TurboTax to Trial Strategy

At its core, Callidus does three things differently:

  1. 10+ Million Case Law Database
    Callidus created its own enriched case database from scratch—an undertaking only the likes of Westlaw or LexisNexis had done before. Their AI agents tag, structure, and extract metadata from court decisions to surface not just relevant precedent, but the “why” behind each ruling.

  2. Visual, Interactive Workflows
    “We’re not a chatbot interface,” McCallon says. “We’re TurboTax for litigation.” Instead of forcing lawyers to prompt their way through problems, Callidus offers guided, visual flows tailored to the legal task, whether that’s building a timeline from 50,000 documents, drafting a motion, or preparing an oral argument.

  3. Agentic, Stepwise AI Reasoning
    Every step in the Callidus platform is multi-threaded and engineered. RAG pipelines, recursive lookups, model switching (e.g., GPT-4o, Gemini 2.5, Grok), and parallel retrieval chains all work behind the scenes.

A Growing Movement Among Litigators

Callidus now serves over 1,000 legal teams, with its fastest adoption among:

  • Generalist litigators at small-to-midsize firms

  • Family law and white-collar defense attorneys

  • Appellate lawyers using its new oral argument simulator (complete with an AI “judge”)

“The lawyer stays in the loop, but they’re not stuck doing drudge work anymore,” McCallon explains. “We’re helping them get to higher-quality outcomes, faster.” And because Callidus isn’t aimed at replacing lawyers with consumer-facing bots, it avoids unauthorized practice of law concerns. “The legal system is too complex and nuanced for AI to run solo,” McCallon says. “And we’re okay with that. We want to empower lawyers, not bypass them.”

What’s Next: The Full Litigation Lifecycle

Callidus closed a $10M round this year, bringing total funding to $13M. With this funding, the 12-person Callidus team is doubling down on engineering, product, and legal domain experts to build what McCallon calls “cradle-to-verdict” coverage.

“We want to support the full litigation lifecycle, from the first intake call to trial prep. That means automating background work while surfacing the insights attorneys would otherwise miss.” Their north star metric is a 7x YoY growth in ARR, driven almost entirely by product-led growth. Still, McCallon doesn’t shy away from the big question: What should the legal system look like in an AI-enhanced world?

“We need a more efficient legal system,” he says. “The costs are too high for individuals, and the system is too slow for companies. But we also can’t create a world where everyone sues everyone because AI makes it easy.”

His solution: smarter AI tools paired with better system design, like loser-pays models or case routing guardrails. “We need balance. AI can make justice more accessible, but only if we do it right.”

Callidus may not be shouting from the rooftops, but it’s quietly giving thousands of lawyers superpowers. And in the world of litigation, that’s how revolutions begin.

Tags: AI startupsMcKinney startupsVC-backed startups
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Nima Olumi

Nima Olumi

Nima Olumi is a writer and CEO. He covers topics such as software, business, and economics. In his free time he mentors inner city youth at Squash Busters.

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