Lead with Confidence. Empower Your Team. Thrive as a Founder.

Coaching for founders navigating the challenges of growing teams and scaling fast-moving businesses.

As a founder, your role evolves as your business grows. What once felt exciting—managing a small, close-knit team—can now feel overwhelming as the challenges of leadership expand. Team misalignment, communication breakdowns, and operational demands are pulling you in every direction, leaving little time to focus on your vision.

You don’t have to tackle these challenges alone. Leadership doesn’t have to feel this complicated.

I’m Jocelin Caldwell, and I work with founders of fast-growing businesses to simplify their leadership challenges. Together, we’ll uncover the root of your people problems, develop practical solutions, and help you define a leadership style that empowers your team to grow alongside your business.

What You’ll Gain

  • Clarity: Understand what’s causing friction within your team and leadership.

  • Confidence: Learn how to navigate tough situations and lead with authority.

  • Momentum: Take immediate, actionable steps to resolve your challenges.

  • Sustainability: Build systems that allow your team to thrive independently, freeing you to focus on the big picture.

How It Works

Every session is designed to deliver immediate insights and actionable steps. Here’s what we’ll focus on:

  • Clarify Your Vision: Define what great leadership looks like for you and your growing business.

  • Uncover the Barriers: Identify the underlying issues that are holding your team or leadership back—whether it’s misalignment, unclear expectations, or unproductive habits.

  • Create a Plan: Build clear, actionable solutions that can be implemented today.

  • Anchor Long-Term Success: Develop sustainable habits and systems that keep your team aligned and thriving.

Our work together will move you from managing day-to-day frustrations to confidently leading your team and scaling your business.

About Me

With over 20 years of experience coaching and advising founders and executives, I’ve worked with more than 50 organizations to solve leadership and people problems. From startups to high-growth companies, I understand the unique challenges leaders face as they scale operations and guide teams through transformation.

My approach is practical, tailored, and results-driven. I focus on helping you simplify complexity, empower your team, and free yourself to focus on the opportunities that matter most.

Ready to simplify your leadership challenges and build a culture of excellence?