
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