About Freedom Goal Group
We work with CEOs and leadership teams who have already built successful companies and know what got them here won't get them where they want to go next.
Through the Freedom Goal System®, we help them build the strategy, leadership, and organizational capabilities required to keep growing without everything depending on the CEO.
It Started With Our Founder
Before Jennifer Berkowitz ever coached CEOs, she built and led a company herself.
As a female founder in the technology industry, Jennifer built a multimillion-dollar business in an incredibly competitive market.
And she didn't win by being cheaper.
Her company charged as much as 10 times more than competitors and still won the business.
That required thinking differently about why customers would choose them, how to create value competitors weren't creating, and how to build a company that was genuinely easier to say yes to. But winning the business was only part of the challenge.
As the company grew, Jennifer had to learn how to build the organization behind it. A strong leadership team. Great people. Clear priorities. Financial discipline. Accountability. Strong execution. A culture people wanted to be part of. And eventually, a company that didn't require her to be at the center of everything. The business became highly profitable, earned multiple Inc. 5000 and Best Places to Work recognitions, and Jennifer ultimately sold it.
But what she had really built was a company that could win, execute, and give her choices.
That experience became the foundation for the work she has spent more than a decade doing with other CEOs and leadership teams.
Built Through Years of Doing the Work
Jennifer's experience as a CEO shaped how she thought about business. But the Freedom Goal System® was shaped through more than a decade of working alongside CEOs and teams.
Different industries. Different challenges. Different stages of growth. Some needed to rethink how they won. Some needed stronger financial discipline. Some had leadership teams that needed to operate at another level. Others had great strategies but couldn't consistently execute them. Over time, the patterns became clear.
The strongest organizations weren't great at just one thing. They had developed a set of capabilities that allowed strategy, leadership, people, and execution to work together.
Those became the Six Capabilities at the center of the Freedom Goal System.
And they now give Freedom Goal Group a common philosophy and methodology of work.
Explore the Freedom Goal System
Jenny Rodriguez-Vargas
Workforce Optimization Coach
Introducing Our Freedom Goal Group Faculty
Experienced coaches and practitioners who help leaders think differently, elevate how organizations operate, and build organizations capable of extraordinary results.
Each member of our faculty brings deep experience, expertise, and perspective to the work. They teach. They coach. They challenge thinking. And they work alongside leaders on the real business in front of them.
Different expertise. One shared philosophy and methodology for building extraordinary organizations.
Additional faculty members coming soon.
Meet Jennifer Berkowitz
Founder, Freedom Goal Group
Jennifer Berkowitz is an entrepreneur, former technology CEO, and business coach with more than 30 years of business experience and more than a decade coaching CEOs and leadership teams.
Before becoming a coach, Jennifer founded and built BUMI (Backup My Info!) into a multimillion-dollar, debt-free, and highly profitable technology company. BUMI earned multiple Inc. 5000 and Best Places to Work recognitions before Jennifer successfully sold the company to J2 Global in 2014.
Since then, Jennifer has worked alongside mid-market CEOs and leadership teams to strengthen strategy, profitability, leadership, and execution. She has co-led Scaling Up's Coach Certification Course and mentored many Scaling Up coaches.
Jennifer's work has been featured in The Wall Street Journal, The New York Times, Money Magazine, and Crain's New York Business, and she wrote the weekly “A CEO's Journey” column for The New York Times. She is a graduate of the Entrepreneurial Masters Program and has been an active member of Entrepreneurs' Organization (EO) for more than 20 years.
Why Freedom Goal™?
Freedom Goal Group is part of R&J Advisory Group, the company Jennifer created after selling her technology business. R&J stands for her two boys, Ryan and Jake.
When Jennifer sold her company, she knew she had created a financial legacy for her family. But years later, she realized there was another kind of legacy she hadn't created. Everything she had learned about building a business was still in her head.
The lessons. The mistakes. The frameworks. The questions she had learned to ask. Everything she had learned from building her own company and from years of working alongside CEOs and leadership teams.
As an older mom, that started to matter. She wanted to take everything she had learned and turn it into something that could live beyond her. Not because she expects her boys to follow in her footsteps, but because if they ever decide to build or lead something of their own, she wants them to have access to the lessons it took her decades to learn.
Freedom Goal Group is her way of turning what was in her head into something she can leave behind. It's a business she's incredibly proud to build. But it's also a love letter to her boys.
And there's another reason the name Freedom Goal means so much.
When Jennifer sold her company, she realized that what she had built gave her something beyond financial success. It gave her choices. The choice to stay involved or step away. To build something new. To spend more time with the people she loves. To decide what she wants the next chapter to look like.
That's what we want for every CEO we work with: to build an extraordinary company they're incredibly proud of, one that can win, execute, and thrive without everything depending on them. A company that gives you choices about what you want to do next.
That's the Freedom Goal.
Let's Talk About Your Organization