I was once a struggling CEO too...
My name is Jennifer BerkowitzÂ
I know what it’s like to be stuck, overwhelmed, and unsure how to scale without burning out. Years ago, I built a tech company from the ground up. It was growing, but I was exhausted and  too involved in the day-to-day.  I knew something had to change.
Everything shifted when I implemented the Scaling Up methodology. We clarified our strategy, charged 10x more than competitors, and still won business. Profit soared, my team stepped up, and for the first time, I had my life back.
I learned to lead instead of carrying it all and eventually, I exited the business, achieving both financial and time freedom.
Now, I help other CEOs and leadership teams do the same: build wildly profitable businesses that thrive without them, so they can finally reach their version of freedom.
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- Maybe growth has stalled or it's happening so fast your infrastructure can't keep up, and you're worried something's about to break.
- You’re stuck in the weeds, constantly putting out fires, and holding everything together while your leadership team waits for direction.
- You’re tired of being the one running every meeting, overwhelmed by the need for a real plan, but can’t find the time or headspace to create it.
- You’re craving freedom, but growth just keeps adding more to your plate.
- Deep down, you want to believe that your business can one day thrive without you… you just don’t know how to make that happen.
What Private Coaching Looks Like
This isn’t coaching-lite. It’s CEO-level advisory for those who are ready to lead, scale, and finally stop carrying the business alone.
When I work with a client, I roll up my sleeves and get deep inside the business because that’s the only way real transformation happens. Here's exactly how we do it:
- Full-Team Business Assessment : We start with a confidential diagnostic completed by your leadership team. This gives me an unfiltered look at where the business is strong, where it’s stuck, and where the real issues lie.
- 1:1 Executive Interviews: I privately interview each leadership team member to uncover misalignments, missed opportunities, and blind spots that don’t show up in group settings.
- Strategic Rebuild: 2-Day Deep Dive: We meet for a focused 2-day strategy session to break down what’s working (and what’s not). Together, we create a clear 3-year vision, a focused 1-year plan, and a 90-day execution roadmap with clear accountability for who owns what.
- Monthly Executive Team Coaching:Â Each month, I meet with your leadership team to keep plans on track, troubleshoot roadblocks, and introduce leadership tools that raise performance and clarity across the company.
- Quarterly Strategy + Reset:Â Every quarter, we reassess, recalibrate, and build your next 90-day sprint. Your strategy stays alive and dynamic not buried in a deck.Â
- Weekly CEO Coaching: You and I meet weekly for strategic 1:1 coaching. We’ll focus on leadership, priorities, and the obstacles in your way so you can lead with clarity, confidence, and control. Â
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This is the kind of support most CEOs don’t even know exists—until they experience private coaching with us.
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If what you’ve read resonates and you're ready—let’s talk.
I work with a limited number of private clients each year and am intentional about who I partner with. If we’re a good fit, we’ll dig deep and get to work. If not, I’ll happily point you in the right direction.
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Apply for private coachingWhat Makes This Different
There are a lot of coaches out there but very few have built, scaled, and exited a business themselves.
I have.
I don’t just tell you what to do. I help you build a business that scales and frees you in the process. No rigid frameworks. No cookie-cutter plans. I meet you where you are, uncover what’s really going on, and bring the right tools to help you scale without chaos.
I bring leadership education into every session
If you want to 10x your business, you need to 10x your team’s capabilities and I help you do exactly that.
Your entire leadership team is involved
I coach them directly during monthly, quarterly, and annual planning sessions so the whole company levels up, not just you.
I run your strategic planning meetings
You get to show up as the visionary instead of running the show, which frees you to focus on the bigger picture.
I go deep before we begin
I interview your leadership team 1:1 to understand what’s really going on, so we can build a plan that actually works.
I’m selective about who I work with
My purpose is to give others the same freedom I’ve earned, but I also live it. That means I keep my schedule intentional, with space for the things I love (like tennis and time with my kids). I only say yes when it’s the right fit, for both of us.
The results speak for themselves
Many clients have seen massive improvements in their profit and revenue, completely transformed their leadership teams, and finally built businesses that run without them.
This is focused, high-impact coaching designed to help you scale with less stress, more profit, and the freedom you set out to build.
Ready to Build a Business that Doesn’t Rely on You?Â
Not Sure If Private Coaching Is the Right Fit?
There are other ways to work together.
If you're earlier in your journey or don’t yet have a full leadership team, I also offer 1:1 CEO coaching designed specifically for founders who still wear most of the hats.
Or, if you're looking to grow your team’s skills and alignment, check out one of my Leadership Academies, built to help teams scale together with clarity and confidence.
No matter where you're starting from, there’s a path to your Freedom Goal™ and I'd love to help you get there.
Apply for private coaching