Evolving with Jessica Nguyen
Molly Finn on Embracing a Nonlinear Career
Oct 30, 2026 · 46 min
Eighteen years at one company rarely means a straight line, and Molly Finn's career proves it. From a startup thrown into chaos to nearly two decades at eBay, her path was anything but linear, and she's using that same restless curiosity to make sense of what AI means for the next generation of lawyers. Jessica sits down with Molly Finn, Advisor at Sandstone, to talk about her nonlinear legal career, what she has learned building custom AI skills, and why she believes AI will reshape both the legal profession and the tools it relies on.
Meet the expert
Molly Finn
Advisor at Sandstone, to talk about her nonlinear legal career, what she has learned building custom AI skills, and why she believes AI will reshape both the legal profession and the tools it relies on
Eighteen years at one company rarely means a straight line, and Molly Finn's career proves it. From a startup thrown into chaos to nearly two decades at eBay, her path was anything but linear, and she's using that same restless curiosity to make sense of what AI means for the next generation of lawyers.
Key takeaways
01
Molly Finn's winding career path from law school and an MBA to eighteen years at eBay
02
How her first startup job turned her into an employment law specialist in eighteen months
03
Embedding inside Cisco's HR team and treating legal and HR as one shared unit together
04
Why a linear path into law is disappearing as AI reshapes early-career legal work now
05
Building a custom Claude Skill for her resume and catching where the AI quietly drifts
06
Why general AI models still fall short compared to legal-specific, filtered AI tools
07
Trust, walled data, and the risk of leakage across different AI tools in one company
08
The coming rise of an agent officer role built to monitor and manage AI agent drift
09
Rethinking the legal tech stack to make tools genuinely easy to use, fun, and simple
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