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Guiding Growth Through Experience, Reflection, and Change

I help professionals navigate growth, career transitions, and new chapters by blending real-world experience with practical coaching and a human touch.

With over two decades of experience across technology, education, financial services, and entrepreneurship, I've seen firsthand how personal clarity and professional purpose intersect. My approach to coaching is rooted in that experience — combining structured thinking with empathy to help others design careers and lives that feel intentional and rewarding.

Ben Bradley headshot

From Consulting to Global Leadership

Ben Bradley speaking at Dreamforce

My career began with roles in Management Consulting, Higher Education, Private Wealth Management, and co-founding a winery as well as a wine retail business. These early experiences taught me how different industries think about value, growth, and the human side of business.

Eventually, I transitioned into a career in technology, starting as a Commercial Solutions Engineer at Tableau. Over time, I grew into leadership roles, culminating in serving as Global Head of Solutions Engineering.

Across roles at Tableau, Salesforce, and PandaDoc, I had the opportunity to lead global teams, helping organizations design, scale, and mature their presales and implementation strategies as well as refine and develop their leadership practices. Through that journey, I discovered that the most successful teams weren't just technically strong. They were aligned, motivated, and guided by leaders who understood the human side of growth.

What I Learned Along the Way

Along my corporate journey, I was fortunate to work with coaches, leaders and mentors who helped me grow my career, and more importantly, my perspective. Through those experiences, I gained clarity on what truly mattered to me: defining success beyond titles or earnings, and creating a path toward financial freedom and personal fulfillment.

Even after achieving the financial readiness to make changes, I learned that the harder transition is mental - learning to let go of an endless accumulation mindset.

That realization became the foundation of my coaching philosophy: success isn't about doing more, it's about doing what matters with intention.

Today, My Work is About Creating Options

Work in Practice

In addition to coaching, I continue working as a fractional Solutions Engineering leader, helping organizations scale technical teams and processes.

AI Transformation

I also explore how AI can empower individuals, in both professional and personal contexts, to make smarter decisions, scale impact, and create more freedom.

Move Abroad

Beyond tech, I run Prudent Expat, where I help people prepare for and navigate life abroad, and I stay active as an investor in real estate, crypto, and other alternative assets.

My mission across all of these endeavors is simple: to help people design lifestyles that create freedom, growth, and purpose.

Life Beyond Work

Ben and Lisa abroad

I live in Milwaukee, Wisconsin, with my wife and our corgi, Darby. We love exploring new cultures and envisioning where we might live next (Colombia, Ecuador and Spain are currently strong contenders). When we're not traveling, we spend time with family, especially our niece and nephews.

Your Story is Still Being Written

If you're considering a change in your role, your focus, or your stage of life, my focus is to help you bring clarity to the process.

Together, we can define where you want to go and chart a practical path to get there.