About Freedom Goal Group

Freedom Goal Group works predominantly with established, service based organizations doing at least $5 million in revenue or backed by private equity. They've already achieved meaningful success.

They've built a real business. They have a leadership team. And they're ready for what's next.

But they've reached the point where what got them here won't get them where they want to go next.

The organization is stretched. Too much still depends on the CEO and a handful of key leaders. The leadership team needs to operate at another level. And scaling from here requires more than simply working harder.

That's where we come in.

We work deeply with the CEO and leadership team on the business and the people leading it.

Strategy. Financial performance. Leadership. Priorities. Accountability. Execution. People.

We teach, coach, and challenge the team while working on the real business in front of them. And through our Freedom Goal Accelerators™, we develop the leaders throughout the organization who are responsible for turning strategy into results.

At the center of all of it is the Freedom Goal System®, the philosophy and methodology that guides our work.

We build the capabilities the organization needs to break through what's holding it back, scale, and keep getting stronger as it grows.

Let's Talk About Your Organization

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®

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.

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 R&J?

R&J stands for my two boys, Ryan and Jake.

When I sold my company, I knew I had created a financial legacy for my family. But years later, I realized there was another kind of legacy I hadn't created.

Everything I had learned about building a business was still in my head.

The lessons. The mistakes. The frameworks. The questions I had learned to ask. Everything I had learned from building my own company and from years of working alongside CEOs and leadership teams.

And as an older mom, that started to matter to me. I wanted to take everything I had learned and turn it into something that could live beyond me. Not because I expect my boys to follow in my footsteps. But if they ever decide to build or lead something of their own, I want them to have access to the lessons it took me decades to learn. The tools. The thinking. The programs. The experience.

Freedom Goal Group is my way of turning what was in my head into something I can leave behind. It's a business I'm incredibly proud to build. But it's also a love letter to my boys.

Why Freedom Goal™?

Because ultimately, that's what I want for my boys too. And it's what we want for every CEO we work with.

To build something extraordinary without having to hold every part of it together yourself. To build great leaders around you. To build an organization that knows how to win and knows how to execute. To create something that can continue beyond you, whether you eventually sell it, pass it on, or simply decide you want to play a different role. And to know that everything you poured into building your company created something more than financial success.

It created choices. A company that gives you choices about what you want to do next.

That's the Freedom Goal.