We were lucky to catch up with Jennifer Santoso recently and have shared our conversation below.

Jennifer, looking forward to hearing all of your stories today. What do you think Corporate America gets wrong in your industry?

There’s an incredible lack of genuine, natural and effective collaboration across corporate departments and leadership. I pride myself in bringing out people’s talents / genius and facilitate collaboration.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Jennifer Santoso — founder of VAST Leadership Development, where I help teams and leaders rise into clarity, alignment, and purpose. I’m a leadership facilitator, strategist, and speaker with a background that weaves together 18+ years of experience across leadership development, commercial real estate, and government. My work blends business strategy with human-centered transformation.

I got into this work by living it. I started my career in commercial real estate and economic development, navigating high-stakes negotiations, government partnerships, and team dynamics — often as the only woman in the room. Over time, I realized the biggest barriers weren’t the deals or deadlines — they were communication breakdowns, unclear expectations, burnout, and misaligned leadership. I started teaching leadership skills internally and fell in love with helping people unlock their brilliance — especially when the stakes were high.

That passion led me to launch VAST Leadership Development. I now design and facilitate transformational workshops, leadership labs, and executive coaching for teams who want to level up — not just in performance, but in culture. I’ve taught over 600 leadership and soft skills courses for clients like SDG&E, CREW San Diego, and NAVWAR, where I helped one team improve KPIs by over 70%. I also founded Opportunity Knocks, a real estate investing community that grew to 1,000 members and raised $5 million in capital.

The core problems I help solve?
• Leadership teams that are misaligned or unclear on direction.
• Employees who feel undervalued or unsure how to lead without a title.
• Cultures that lack psychological safety, effective communication, or trust.

What sets my work apart is how deeply I integrate business results with relational intelligence. My sessions are not surface-level. They’re experiential, emotionally intelligent, and rooted in real strategy. I’m known for creating space where people feel safe enough to be honest — and brave enough to grow.

What I’m most proud of is the change I witness in people — when someone walks into a session unsure or guarded, and leaves feeling powerful, connected, and clear. Those quiet turning points change careers, teams, and lives. That’s the magic I live for.

For potential clients or partners, I want you to know: I don’t do cookie-cutter training. I meet you where you are, build with you, and co-create something transformational. Whether it’s a workshop, keynote, or coaching engagement, my goal is to help you lead with clarity, courage, and purpose — and create a culture that reflects that.

We’d love to hear a story of resilience from your journey.

Got it — you want the soul and the lesson, not just the polished story. Let’s bring more of your humanity and emotional truth to the forefront — the fear, the growth, and the transformation. Here’s a deeper, more heartfelt version that captures both your leadership and your vulnerability:

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One of the most defining moments of resilience in my career wasn’t a big, flashy success — it was a moment of discomfort, fear, and choice.

I was leading a change management effort for a Department of Defense client, facilitating an intro training to get people grounded in the process. Midway through, in a room full of military professionals, a former commander — now a contractor — blurted out, “Must be nice to stand there and talk for a living, Jennifer.”

The room went dead silent. I felt humiliated. No one said anything. I pushed through and finished the session, but I left rattled.

Over that weekend, I couldn’t shake it. Part of me wanted to just move on — to hope he’d soften over time or forget it happened. But I knew if I didn’t face the tension head-on, I’d risk losing the trust of the room. And more than that, I’d be abandoning myself. Still, I was scared. The idea of confronting a high-ranking man with military clout triggered every anxiety I had about being dismissed, misunderstood, or told I was overreacting.

But on Monday, I asked him to step into a private office. My voice shook a little, but I stayed grounded. I brought up what happened and asked — as calmly as I could — what was behind it.

He shared that he’d worked with change management consultants in the past who wasted time and money. He had built up resentment. And in that moment, I wasn’t a person — I was a symbol of all that frustration.

I told him I understood. I thanked him for telling me. And then I asked him to give me a chance.

He did. And something shifted. Over the course of the project, he became one of my biggest supporters. He advocated for me in rooms I wasn’t in. He even left a glowing review on LinkedIn — calling out my insight, tact, and ability to earn buy-in.

That experience taught me something essential: Resilience isn’t just about pushing through — it’s about facing fear, holding tension, and choosing courage over comfort. It’s what turns hard moments into deep trust. And it’s what I try to model in every space I lead.

What’s a lesson you had to unlearn and what’s the backstory?

A lesson I had to unlearn was that being a warrior — constantly pushing, striving, achieving — was the only way to be worthy.

I grew up in an immigrant household. My mom came from Taiwan, raising two daughters while working, cooking, managing a household, and trying to survive in a new country with no time for herself. She was incredibly gritty — but she was also burnt out and angry. As kids, we felt that tension. We absorbed the message that things were never quite good enough, and that love and approval were earned through achievement.

So I fought. I got the grades, went to UCSD while my sister went to UCLA, landed competitive jobs at companies like Booz Allen and Deloitte, and spent 14 years in defense contracting. On paper, I had done everything “right.” And it did bring my mom a deep sense of joy and pride — it made her sacrifices feel worth it, I’m sure.

But inside, I was crumbling. I felt increasingly misaligned. I worked relentlessly, but I rarely felt seen or valued for who I was — only for how well I could grind. There were occasional bright lights — people who saw my deeper gifts — but overall, that world hardened me. It pulled me further and further from my joy, my soul, and my sense of authenticity.

Eventually, I knew I had to turn the ship around. It was slow, messy, and painful — but I started pivoting toward leadership development. I began facilitating workshops that lit me up. I found my voice. I started dancing salsa again — and yes, salsa dancing helped me remember who I was: expressive, joyful, intuitive.

And the women I met through CREW San Diego played a huge role in that too — they helped refill a part of my spirit that had long been depleted.

So the lesson I had to unlearn? That success is only found in struggle. I learned that alignment, joy, and ease aren’t indulgent — they’re necessary. And when I let those things lead, I not only feel more alive — I’m actually more powerful, more impactful, and more connected than ever before.

Contact Info:

• Website: https://Www.vastleader.com
• Linkedin: https://www.linkedin.com/in/jennifer-santoso-7427394/

Image Credits

Visual Content Agency – Vincent Apodaca
Eckes YMCA