What Makes Lawyers Stand Out to In-House Counsel (with Jessica Nguyen, Deputy General Counsel of DocuSign and Head of Contract Nerds)

About this episode

“Trust is fundamentally about you do what you say you’ll do.” - Jessica Nguyen

How do you get 2,200+ legal professionals to show up for a contracts webinar?

In this episode of So Much To Say: A Legal Podcast for People, Jessica Nguyen, Deputy General Counsel of AI Innovation & Trust at DocuSign and Head of Contract Nerds, joins Megan Senese and Jennifer Ramsey to pull back the curtain on why most law firm marketing completely misses the mark, how DocuSign is using AI to build deeper trust with its clients, and the one outside law firm that truly stood out to her, and what one lawyer did that was different from every other law firm competing for attention.

From building one of the most engaged contracts communities in legal to helping shape AI strategy inside a global tech company, Jessica shares what actually creates momentum, and what kills it.

In this episode, you’ll hear directly from a Deputy General Counsel about:

• Why Contract Nerds consistently attracts thousands of lawyers and what lessons you can apply to your next webinar
• How community becomes a long-term growth engine — not just a mailing list
• What in-house counsel actually look for when hiring outside counsel 
• The positioning shifts that make lawyers stand out instead of blend in
• The CLE mistakes all law firms make and how to change it
• Why legal services feel commoditized and how to break that cycle
• How AI can 10x your legal productivity without replacing your judgment
• Why consistent execution, not just branding is what builds real client trust
• The role gratitude plays in sustaining a long-term legal career

This conversation is for lawyers who want a clearer understanding on how to attract the right clients—without chasing, posturing, or relying on generic marketing tactics.

About Jessica Nguyen:

Jessica Nguyen is Deputy General Counsel of AI Innovation & Trust at DocuSign and Head of Contract Nerds, a global community serving thousands of contracts and legal professionals. A seasoned in-house leader and former Chief Legal Officer, Jessica focuses on customer-centric innovation at the intersection of AI, agreements, and trust.

She also hosts the In-House podcast, where she interviews legal leaders about influence, career pivots, and building a meaningful in-house career.

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If you’re navigating BigLaw pressure, struggling with business development or marketing decisions and want a confidential thinking partner, connect with us here: 

• Learn more about stage
• Connect with Megan Senese 
• Connect with Jennifer Ramsey