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Key insights
1. Community is a Career Multiplier.
Jenn’s own rise began with showing her "crap" Cisco strategy to a peer at Adobe. This led to a New York chapter presentation that immediately triggered recruitment interest from major East Coast legal leaders. Validating your internal ideas against an external community is a powerful navigation point for professional growth.
2. The "Chapter Approach" to Career Stability.
Legal operations is an exercise in long-term organizational transformation. Jenn advises mentees to give each job a three-year "chapter". This longitudinal focus allows a professional to see the full arc of a project—from implementation chaos to established win—providing the necessary depth to speak authoritatively in future roles.
3. Project Management as the Foundation.
If an ops professional can only master one hard skill, Jenn biases heavily toward project management. While communication is vital, failing to run a project effectively leads to a loss of user engagement during massive implementations, like a new CLM system. Leading without authority is a core component of this skill set.
4. Failure is the Instructor of Complex Systems.
Citing astronaut Eileen Collins, Jenn emphasizes that in complex systems, the only way to truly learn is through the "red light" of failure. She advocates for constant "retros" to analyze what went wrong and how to avoid repeated errors, suggesting that humility in the face of failure is essential for a growth mindset.
5. CLOC Strategy: Moving from Events to Dialogue.
As CLOC President, Jenn aims to thread community events through content creation and into deeper "conversations" or dialogue. She intends to introduce a formal career framework during her term to help ground members in their professional journeys and turn spotlighted members into "content kings" of specific subjects.
6. Closing insight
The legal operations field is still defining its own boundaries; the most successful leaders are those who treat their careers as a series of iterative sprints, using community as their primary navigation point.
In this podcast, we cover
0:00 Introduction
3:45 Advancing the legal ops industry at CLOC as President of the Board of Directors
7:41 Getting started with CLOC
11:48 Unpacking the mindset of service and giving back
14:59 Lessons learned as CLOC president
18:14 Advice for professionals getting their start in legal ops
23:00 Hiring detail-oriented staff with stakeholder management skills
27:10 Recommending platforms for learning project management skills
31:42 Dealing with the loneliness of a one-of-one role
38:42 Legal ops as a business team vs legal ops as a legal team
42:48 Focusing on the future
48:46 Maintaining an after-hours music career
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