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Actionable
Takeaways
Master zero-friction PLG for professional services:
Callidus achieved 1,200 customers and 100% quarterly growth by eliminating traditional B2B sales friction. Justin explained their approach: "Initially we did this with zero touch points, zero friction. You don't need to talk to anybody. It's basically just you come to our website, you sign up for a trial, you start using the app." This model works particularly well for professional services where individual practitioners can make purchasing decisions independently.
Focus on high buyer-intent keywords for performance marketing success:
Rather than casting a wide net, Callidus targeted specific, high-intent search terms. Justin emphasized: "A lot of people focus on words that maybe are too informational with lower buy intent." They focused on keywords like "legal AI assistant" and "legal AI research" that indicated immediate need rather than general curiosity. Founders should prioritize keywords that align with their ICP and indicate purchase readiness.
Create organic acquisition through valuable free resources:
Callidus moved their entire 11 million case database to the web for free access, creating a powerful organic acquisition engine. Justin described the strategy: "People have free access to every case that we have. And they can search, say Brown versus Board of Education. And we'll be one of the groups that has a page dedicated to that." This approach generates organic traffic while demonstrating product value, creating a natural conversion funnel from free users to paid customers.
Optimize every funnel step with ruthless precision:
Callidus's performance marketing success came from methodical funnel optimization. Justin broke down their approach: "Every step of the funnel. Break it down. What conversion rate are we seeing on this step of the funnel? What's benchmark? And then for the areas that are below benchmark, why are we not doing well?" Founders should treat each funnel step as a conversion problem to solve, using data to identify bottlenecks and creative solutions to address them.
Build trust through domain expertise, not just technology:
In conservative industries like law, trust is built through demonstrating deep domain knowledge. Callidus differentiates itself by combining legal expertise with engineering: "We have really visual multi step workflows, we have really deep engineering, we've tied both the legal knowledge and the engineering expertise." Founders entering regulated or conservative industries should emphasize domain credibility alongside technical capabilities.
Use evaluation systems to optimize AI model performance:
Rather than fine-tuning models, Callidus built comprehensive evaluation systems to optimize performance across different foundation models. Justin explained: "We've gone through and had lawyers say, hey, here's my case I've worked on in the past. Here are all of the cases I would reference here... Then we can say, okay, it looks like for this API call, GPT-4 is the best, and this one's Claude." This approach allows for dynamic optimization without the overhead of model training.
Conversation
Highlights
Most B2B founders would call it professional suicide: launching a legal technology company with zero sales team, zero discovery calls, and zero human touchpoints in the buying process. But Justin McCallon, co-founder and CEO of Callidus Legal AI, proved the conventional wisdom wrong. In a recent episode of Category Visionaries, Justin revealed how his contrarian approach to go-to-market strategy helped Callidus achieve 1,200 customers and 100% quarter-over-quarter growth in one of the most conservative industries in business.
The Zero-Friction Gambit
The legal industry has always been relationship-driven, with purchasing decisions typically requiring multiple stakeholder meetings and lengthy evaluation processes. Justin’s team took the opposite approach entirely.
“Initially we did this with zero touch points, zero friction,” Justin explains. “You don’t need to talk to anybody. It’s basically just you come to our website, you sign up for a trial, you start using the app. If you like it, you stay on. If you don’t, you cancel and you’re off.”
This wasn’t a naive oversight or budget constraint—it was a deliberate strategic decision based on a deep understanding of their target customer: individual litigators who make their own technology decisions and despise traditional enterprise sales processes.
The results validated their thesis immediately. “We grew 100% last quarter using that approach. We’ve got 1200 customers,” Justin reports. But the path to this success required more than just removing sales friction—it demanded obsessive attention to every other aspect of the customer acquisition funnel.
The Performance Marketing Machine
With no sales team to generate leads, Callidus became laser-focused on performance marketing optimization. Justin’s approach reveals the level of precision required when every conversion matters.
“Every step of the funnel. Break it down. What conversion rate are we seeing on this step of the funnel? What’s benchmark?” Justin describes their methodology. “And then for the areas that are below benchmark, why are we not doing well? What can we improve?”
This obsessive optimization became critical to their success. When their Google ads optimization algorithm reset, performance dropped dramatically. “Sometimes we’ll realize like, hey, for some reason there was like a reset or something like that, and we’re like, why did we go from 40 customers a day to three?” Justin recalls. The incident highlighted how dependent their growth engine had become on precise algorithmic performance.
Their keyword strategy also departed from conventional wisdom. Instead of chasing high-volume terms, they focused exclusively on buyer intent. “A lot of people focus on words that maybe are too informational with lower buy intent,” Justin notes. “We figured out what the right keywords were to target within our ICP that aligned to our product with high buy intent.”
Turning Product Assets Into Acquisition Channels
Perhaps Callidus’s most innovative growth strategy involved transforming their core product asset into an organic acquisition engine. The company maintains a database of 11 million U.S. cases, which they made freely searchable on the web.
“One of the exciting things we did was move our full case database to the web,” Justin explains. “This means that people have free access to every case that we have. And they can search, say Brown versus Board of Education. And we’ll be one of the groups that has a page dedicated to that.”
This strategy created a natural funnel from free users to paid customers. Lawyers searching for case law would discover Callidus pages ranking highly in search results, experience the quality of their legal data, and then notice the AI-powered research features available through trial signup.
“Hopefully you’re like, hey, this is pretty interesting. This company keeps coming up over and over. I see that they have this AI feature where I can do a deeper case search,” Justin describes the intended user journey.
The approach exemplifies what growth experts call “product-led growth”—but with a twist. Instead of requiring users to sign up for free access, Callidus made valuable functionality completely public, reducing friction even further while building organic search authority.
Rethinking AI User Experience for Professionals
While many legal AI companies built chatbot interfaces, Callidus took a fundamentally different approach to user experience design. Their insight: professionals working on complex tasks need structured workflows, not open-ended conversations with AI.
“We do very visual multi step workflows that really differentiate from chatbot based tools,” Justin explains. “So think like TurboTax, you know, you’re doing your deductions and you know you’re moving on into different areas.”
This TurboTax comparison isn’t casual—it reflects a deep understanding of how professionals prefer to work with software. Rather than asking lawyers to formulate the right prompts for an AI assistant, Callidus created guided workflows that anticipate the shape of legal work.
“We know the shape of every type of answer on every step,” Justin notes. This knowledge allows them to build specific engineering optimizations for each workflow stage. “We’re going to be looking up statutes we need to build in engineering on that step to find the right statutes to eliminate hallucinations, to add accuracy.”
Building Trust Through Domain-Specific Engineering
Trust represents perhaps the biggest challenge for AI companies entering conservative professional markets. High-profile cases of lawyers getting sanctioned for submitting AI-generated briefs with fabricated case citations have created widespread skepticism about AI tools in legal practice.
Callidus addressed this challenge through a combination of compliance investments and engineering sophistication. “We’re SOC 2 compliant, we’ve built out an extensive set of privacy tools, we have a lot of security implemented end to end and then we do a lot to eliminate hallucinations,” Justin explains.
Their approach to AI optimization also differs from typical fine-tuning strategies. Instead of training custom models, they built evaluation systems to optimize performance across different foundation models for specific tasks.
“We’ve gone through and had lawyers say, hey, here’s my case I’ve worked on in the past. Here are the all of the cases I would reference here,” Justin describes their process. “Then we’ll say, okay, let’s run one of the models, let’s run Claude 4 through it, let’s run GPT 5 through it, and so forth. And let’s see what score they get based on our scores of all the different evals we have.”
This allows them to route different types of legal queries to whichever foundation model performs best for that specific task, rather than committing to a single AI provider.
The Engineering-First Organization
Callidus’s go-to-market success enabled an unusual organizational structure that prioritizes product development over traditional business development activities. “We had almost all of our team, we engineers or work engineers and product people, and they can focus on just be visionary, think about the solutions you’re building, how can we drive the biggest impact,” Justin explains.
This structure protects the product team from the typical enterprise software trap of building custom features for large clients. “Don’t be swayed because we have a really big client that says this is what they think they need and they want you to stop everything and go build it for them,” Justin notes. “We can build for the whole industry.”
The approach reflects confidence that product-led growth can scale without traditional enterprise sales motion—at least in the early stages of company development.
Lessons for B2B Founders
Callidus’s journey offers several counterintuitive insights for B2B founders, particularly those building in conservative professional markets:
Question conventional sales wisdom: Even in relationship-driven industries, individual practitioners may prefer self-service options over traditional sales processes.
Optimize ruthlessly when sales isn’t an option: Without sales teams to generate leads, every aspect of the acquisition funnel requires precision optimization.
Turn product assets into acquisition channels: Core product functionality can become powerful organic marketing engines when made freely accessible.
Structure beats conversation for professional workflows: Professionals often prefer guided experiences over open-ended AI interactions.
Domain expertise trumps general AI capabilities: Building trust requires demonstrating deep understanding of industry-specific challenges and requirements.
Justin’s approach at Callidus demonstrates that even in the most traditional industries, there may be room for radically different go-to-market strategies—if you understand your customers deeply enough to challenge conventional assumptions about how they prefer to buy.
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