In this episode of How They Scaled It, I sit down with Scott Kveton, Co-Founder and CEO of CaseMark, who has a track record of building companies that define categories. 

Scott shares how intuition, scrappiness, and relentless customer focus shaped his journey, and why AI is set to transform legal tech in the same way the iPhone reshaped mobile.

00:00:13 – Scott on brand-building struggles and leaning on experts

00:00:52 – Courtney introduces Scott’s career journey

00:01:39 – The three T’s: team, tech, timing

00:03:06 – Learning to trust your gut as an entrepreneur

00:04:28 – Investor skepticism and TAM projections

00:07:08 – Urban Airship’s scrappy early launch

00:09:26 – Lessons from Twilio’s Jeff Lawson

00:12:18 – Why legal tech? The problem CaseMark solves

00:14:39 – Starting small with “easy buttons”

00:16:47 – Why AI will increase litigation

00:20:59 – Simplifying the product for attorneys

00:23:32 – Scaling medical chronology automation

00:26:34 – CaseMark’s subject matter advantage (Scott’s wife as advisor)

00:29:18 – The future of AI collapsing tools in legal

00:30:04 – Scott’s evolving leadership style

00:34:46 – Branding lessons

00:38:59 – Advice for legal tech founders

00:42:12 – What Scott wishes he knew at CaseMark’s start

00:44:19 – Where to find CaseMark and connect with Scott