About Jen

I've spent nearly 20 years navigating the legal profession—from a top technology law firm to a Fortune 5 legal department to serving as General Counsel at an early-stage, venture-backed startup. I've led teams across three continents, launched innovative products at the intersection of regulated industries and new technology, and earned the promotions that in-house counsel are told to want.

I started at Wilson Sonsini Goodrich & Rosati, one of the leading law firms for technology and startups, in 2008, just as the recession hit and layoffs began. I learned to put in the hours, that the best lawyers are the ones people want to work with, and to always have a backup plan.

I spent more than a decade at Amazon, scaling legal teams across some of the company's most innovative ventures - from Prime Air (both the drones and the airplanes) to developer tools that put Alexa in vehicles. I managed global teams, took an international assignment in Asia supporting Customer Fulfillment and Transportation businesses from Tokyo to Bangalore to Dubai, and learned what it takes to lead a legal organization at scale.

Most recently, I served as General Counsel at Auger, where I was employee number five and the only lawyer. I built the legal function from the ground up, navigating the unique challenges of early-stage startups.

And then I made a choice that doesn't fit the traditional narrative.

In early 2026, I stepped away from the GC role. The seat at the table I'd spent almost two decades building toward. Not because I failed. Not because I couldn't handle it. But because the math stopped working.

As the sole lawyer at a startup, the demands grew as the company grew — exactly what you want to happen. But my commute was Magnolia to Bellevue, which meant 90-minute drives home on bad days. My toddler’s bedtime is 6:30. Not 6:30-ish. To have any time with her, I needed to leave by 4pm. But 4pm is when everyone at a startup finally frees up to meet or help turn drafts.

I could see the collision coming at me. And I had to choose.

That choice felt especially significant given my history. I'd spent 15 years operating from a place of fear—fear of layoffs, fear of not being essential enough, fear that choosing anything other than advancement meant falling behind. The 2008 recession shaped that. But with the benefit of 15 years of hindsight, sometimes the riskiest choice is staying too long in something that doesn't work.

Instead of “opt-ing out” I chose to “opt-in” - to my family, my values, and to creating a new version of work structured around flexibility. That choice is why I returned to Encore Explorer. I know that transformation requires someone who's been there and will go there with you, to the questions that don't have easy answers.

Why I Coach the Way I Do:

I know what it's like to work in systems that expect you to figure it out on your own, often under managers who were never taught to develop talent. I've navigated unfamiliar cultural norms on international assignments and felt the pressure to prove myself in new markets. I've wrestled with my own perfectionism, imposter syndrome, risk aversion, and difficulty with self-advocacy. And I've faced the choice between advancement and what truly matters.

This is why my approach is caring candor. I challenge you directly because I care personally about your transformation. I've made the calls, managed the politics, earned the promotions—and walked away when it was right. I bring all of that lived experience to help you examine what you can control, name what's holding you back, and chart your path forward.

Beyond Coaching:

I'm a writer with thousands of followers on LinkedIn, where I share insights on legal leadership, career navigation, and the honest realities of in-house practice and parenting. I've also written for legal tech startup Lexion.ai and am always tinkering with ideas for my first novel.

I'm also a toddler mom, which means I understand the complexity of building a meaningful career while building a meaningful life, and I know what it's like when career ambitions and caregiving demands peak simultaneously.

Let's Talk:

If you're ready to explore, let’s begin with a conversation.

Currently accepting one new client per month.