Alex Herrity and I chat with Laurie Ehrlich about her bold recent move leaving the security of a public company (as Chief Commercial Counsel at Datadog) for the dynamic world of AI startups, joining Dioptra - an AI native legal tech startup revolutionising contract negotiation.
Laurie reveals how she reframed the perceived risk to the decision by giving herself a two-year window, viewing it as "getting paid to get an MBA" while building her personal capital, even if her financial bottom line temporarily plateaued.
What emerges is Laurie's contagious excitement for the problems she's solving. As a self-described "contract nerd," her enthusiasm peaks when she shares her vision for contract stratification and how AI will fundamentally reshape legal contracting and negotiation: "I think generative AI is going to transform how contracting is done. In five years.. it's not gonna look like it looks today."
Beyond the technology, Laurie offers candid insights about the personal growth that comes with being "in the room" for every decision at a startup, from developing empathy for sales to learning to run GitHub jobs. She discusses the freedom of not being told to "stay in your lane" and the challenges of adapting to a startup mentality where perfect must sometimes give way to progress.
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