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What Law School Didn’t Teach Me: Real Lawyering & Building an In-House Career
What Law School Didn’t Teach Me: Real Lawyering & Building an In-House Career
Key insights
1. Sales experience is a "cheat code" for commercial lawyers.
Working in sales operations allowed Flora to understand the "deal cycle" and the various agendas of the people involved before she was a lawyer. This background helped her empathize with the urgency sales teams feel and differentiate between actual business "fires" and standard pressure.
2. The "In-House Generalist" functions like a quarterback.
Product counseling requires a "General Contractor" mindset where the lawyer oversees various disciplines—such as privacy, marketing, and regulatory—to help the business build a product that can be sold safely. It is about navigating gray areas where hard red lines rarely exist, especially in highly regulated sectors like insurance.
3. Prioritize high-impact mentorship over initial salary.
Flora advocates for "playing the long game" by choosing roles based on the quality of training rather than titles or pay. Her formative years at Vendavo provided a foundation where she was allowed to "fail and fall”— a practical experience that law school could not provide.
4. AI is a specific tool for the tool belt, not a general replacement.
While AI can make specific tasks or days easier, it often lacks the deep business context required for complex legal work. Effective lawyering involves knowing when AI is the right "screwdriver" for the job and when a human touch is required to augment the output.
5. Closing insight
The modern in-house lawyer is a teammate, not a bottleneck. By fostering a culture of mentorship and prioritizing business context, GCs can transform their legal team into a strategic partner that helps get the business to "Yes".
In this podcast, we cover
00:00 Introduction
05:09 Why Flora chose law school: early motivations, prestige, and evolving definitions of success
08:58 Pre-law-school experiences: Capitol Hill, journalism, and the wine industry
11:00 Lessons from sales ops: empathy, urgency, relationship-building, and “getting to yes.”
19:40 Flora’s law school reality: difficulty, mindset shifts, internships, and finding purpose
21:59 Why practical experience mattered more than grades and how internships shaped her path
29:40 First in-house role at Vendavo: mentorship, training, and learning by doing
38:37 Knowing when to move on: stagnation, personal change, and leaving Vendavo
40:00 Joining Asana and Axiom, working with Google: scale, contracting models, and risk exposure
48:52 Transition to AppFolio and moving into a product counsel role
51:36 What product counsel actually does: partnering with product teams and shaping decisions
53:06 Learning regulated environments: insurance law, licensing, and NAIC frameworks
55:01 Learning to Think Like Product Counsel: Curiosity, Context, and Judgment
01:02:01 AI in legal work: when it helps, when it doesn’t, and why judgment still matters
01:07:33 Closing reflections: advice to her law-school self, long-game thinking, and becoming self-sustaining
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