Choosing the Right Legal Tech in the Age of AI, with Scott Clasen
Lawyerist Podcast
Using LLMs to augment existing SaaS (HubSpot example)
Scott shares how they use Claude cowork to pull custom reports and augment HubSpot capabilities.
Most law firms don’t have a tech problem. They have a decision-making problem.
In episode 611 of the Lawyerist Podcast, Zack Glaser talks with Scott Clasen about how to evaluate legal technology in a world where AI is changing everything and somehow making it more confusing at the same time.
Too many firms are stuck buying more tools, chasing new features, and hoping the next platform will finally fix their workflow. Scott challenges that approach by shifting the focus away from software and back to systems, asking a more important question: what problem are you actually trying to solve?
They explore the rise of AI-powered SaaS, the appeal of building your own tools, and why “AI-enabled” doesn’t always mean “useful.” The conversation also breaks down how to evaluate legal tech vendors, what contextual AI actually means, and how to think about long-term investments when the landscape keeps shifting every six months.
If your tech stack feels bloated, expensive, or underwhelming, this episode offers a smarter way to make decisions that actually move your firm forward.
Listen to our previous episodes on Legal Tech, AI, and Smarter Law Firm Systems.
- #590: Innovating Without Overwhelm: Practical AI Tips for Lawyers, with Graydon Trusler Apple | Spotify | LTN
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Chapters / Timestamps:
00:00 – Introduction
02:00 – Lawyers Lab Updates
03:55 – Meet Scott Clasen
05:30 – SaaS Is Dead… Or Not
06:45 – Building vs Buying Legal Tech
08:30 – Paying for Tools You Don’t Use
09:20 – AI Isn’t Always the Answer
10:45 – Context Is What Makes AI Useful
13:20 – AI That Works Like a Team Member
15:10 – Making Smart Tech Investments
16:30 – Start with the Problem, Not the Tool
18:30 – Fixing Broken Workflows
20:10 – When AI Does More Than Your Software
21:50 – Custom Software Is Back
23:15 – Where Your Data Should Live
25:40 – The Build vs Buy Decision
27:50 – Is This a Tech Revolution?
30:10 – What Will Survive in Legal Tech
32:00 – Where AI Is Heading
33:30 – Closing Thoughts
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