In this episode, Rob sits down with Jennifer Berkowitz, founder of R&J Advisory Group and Freedom Goal Group, and a seasoned coach to mid-market CEOs and leadership teams. Jennifer shares what it really takes to scale a company—without becoming the bottleneck or burning out. From building alignment across teams to leading remote employees with intention, she offers practical strategies for creating clarity, reducing stress, and empowering teams to drive growth. If you're a business owner stuck in the weeds or unsure how to get your team rowing in the same direction, this conversation is for you.

Scaling successfully isn’t about doing more—it’s about doing less yourself. CEOs must stop trying to be the hero and start building teams that are clear, empowered, and aligned. With the right tools, systems, and rhythms in place, business owners can reduce stress, unlock profit, and grow sustainably—even with remote or hybrid teams

What are the most common growing pains you see in mid-market companies?

How can business leaders make sure their teams are aligned with company goals?

What mindset shift do CEOs need to make to grow more effectively?

How can a better dashboard reduce stress and increase clarity?

What are the biggest challenges of managing remote and hybrid teams—and how can leaders overcome them?

How do you know when someone isn’t the right fit for your organization?

Why do business owners sometimes need to “slow down to speed up”?

Where can people learn more about your work and upcoming trainings?

More About Jennifer Berkowitz:

• Check out R&J Advisory Group and Freedom Goal Group.

• Connect with Jennifer on LinkedIn.

More About Rob Levin & WorkBetterNow:

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