Clio is one of BC’s most successful tech companies — a Vancouver-founded legal software company that now boasts 150,000+ users across multiple continents, a headcount of 1,500, and estimated ARR north of $250 million. But that scale didn’t happen overnight.
At Vancouver Startup Week 2025, Clio’s CMO Reagan Attle and CTO Jonathan Watson (AI illustrations above) joined us for a live panel to reflect on the company’s growth journey — from scrappy startup to global category leader — and share what founders can learn from the inside.
Here are five tactical takeaways from the conversation:
1. Protect your culture — even as you grow
In Clio’s early days, co-founders Jack Newton and Rian Gauvreau personally interviewed every new hire, even when the team hit 400+. “They were setting the cultural bar,” said Watson. That bar included what they called “the asshole check” — a final screen to ensure alignment with the company’s values.
As the team scaled, Clio formalized that bar into a cultural interview process that still eliminates 20–25% of candidates. “Values are your ticket to ride,” said Watson. “If you can’t live them, you can’t stay.”
2. Build the product your customers want — not just what you can monetize
Attle and Watson emphasized that pricing strategy should follow product-market fit, not the other way around. “We’ve always started with: is this actually useful?” said Watson. “If the answer is no, we throw it out — even if we could make money from it.”
That product-first mindset came through in the company’s customer success focus — like Clio co-founders answering support tickets themselves in the early days, and engineers joining support calls to hear customer pain points firsthand.
3. Change is hard — so meet your market where it is
Legal tech is a traditionally slow-moving sector, so getting customers to switch from paper systems or legacy software wasn’t just a product challenge — it was a change management challenge.
Clio’s approach? “We invested heavily in thought leadership and education,” said Attle. Early webinars weren’t just about Clio’s product — they were about why the cloud was safe and how technology could drive compliance. The company also built credibility through partnerships with bar associations and law societies.
4. Retention fuels flexibility
Attle credited Clio’s high customer retention rates with enabling its full-funnel investment strategy. “We can afford to invest in product, sales, onboarding — because customers stay,” she said.
That longevity allowed Clio to blend inbound and outbound sales motions, develop its enterprise offering over time, and invest in higher-touch sales despite starting in the one-to-four user solo firm space.
5. Don’t chase AI hype — but don’t ignore it either
Clio is bullish on the potential of AI — but patient with implementation. “We don’t need to be first — we need to get it right,” said Watson. “This is people’s legal data. We can’t afford to break trust.”
Internally, Clio encourages teams to use AI tools like Cursor and ChatGPT, running internal challenges and training to share wins across teams. Engineers using AI are reportedly shipping up to 3x more code — though with higher reversion rates — while marketing teams are piloting AI to summarize interviews and draft first-pass copy.
Bottom line:
You don’t need to be in legal tech to learn from Clio. Whether you’re hiring your next team member, launching a second product line, or figuring out how to break into a legacy industry — their journey offers a masterclass in scaling with discipline, empathy, and long-term thinking.