Outsider Insights | What We Learned Helping CEOs Grow in 2025

Outsider Insights

Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.

2025 in Review

Across Chief Outsiders, we worked with hundreds of CEOs this year—from tech companies to manufacturing powerhouses, service firms to healthcare innovators. While the industries varied, the underlying leadership questions were often the same: How do we scale smarter? Where do we invest next? Are we structured to seize the growth that's right in front of us?

Here are a few things we learned helping CEOs answer those questions in 2025:

1. The Shift to Scalable Systems Is No Longer Optional

Many of our 2025 engagements started with a similar CEO insight: "What got us here won't get us there." Founders, rainmakers, and scrappy growth tactics had hit their limits. The next phase required structure.

This year, we:

• Built scalable sales engines to replace personality-driven selling

• Created measurable, repeatable processes for client retention and expansion

• Unified fragmented marketing efforts into disciplined, data-backed strategies

From SaaS to industrials, this wasn't about starting over. It was about building on success—with systems that could support $20M, $50M, or $100M growth.

2. CEOs Need Execution, Not Just Strategy

Yes, vision still matters. But in 2025, we saw a growing hunger for help moving from strategy to action. CEOs didn’t want another plan—they wanted someone who could own the result.

Over the course of the year, we:

• Stepped in as interim revenue leaders to drive progress while hiring caught up

• Rebuilt underperforming marketing teams and restructured sales orgs

• Aligned disconnected tech stacks and rebuilt CRM and reporting foundations

Whether it was a stalled GTM launch or a client success team stretched thin, the pattern was clear: The playbook matters—but so does having the bench to run it.

3. Brand Clarity Is a Hidden Growth Lever

As companies expanded—organically and through acquisition—many leaders found themselves asking a deceptively simple question: "What do we stand for now?"

This year, we helped:

• Multi-brand firms simplify and unify their messaging

• Mid-market players reposition to reflect evolving offerings and customers

• Executive teams align around a core story that resonates internally and externally

When you clarify your position, everything else moves faster—sales, hiring, innovation, and investor alignment.

Where We Worked in 2025

This year’s engagements spanned a wide mix of industries. Here’s where CEOs most frequently called on us:

• Professional Services – 26%

• Tech & SaaS – 24%

• Consumer – 16%

• Healthcare – 16%

• Financial Services – 11%

• Private Equity PortCos – 5%

• Nonprofit / Social Impact – 2%

We served companies from $10M to $300M in revenue, with one unifying thread: transformation that needed traction.

What This Tells Us About 2026

Many of the CEOs we worked with weren’t struggling with growth. They were struggling with the weight of growth—outdated systems, overloaded teams, unclear positioning. The opportunity was there. The friction was internal.

As we head into 2026, we believe the winners won’t just be those with the best product or most capital. They’ll be the ones with clarity, alignment, and a strong operating rhythm from first contact to renewal.

Here’s to building with discipline, scaling with confidence—and helping more great companies grow in the year ahead.