Outsider Insights
Across Chief Outsiders, we talk to hundreds of CEOs every month. In this new 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.
From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
In our conversations with CEOs this month, one challenge keeps surfacing: the sales function is not scaling with the business opportunity.
Many of these companies aren’t in crisis — they’re growing or see tremendous growth opportunity. Some are even outperforming their industries. But the growth they’ve fought hard to earn – or are ready to realize – is now exposing structural cracks in their sales systems: inconsistent results, unclear accountability, and a team flying blind without a clear playbook.
It’s not that these CEOs haven’t been thoughtful. It’s that what got them here—hustle, intuition, relationships—is no longer enough.
Why Sales Breaks First
In founder-led or second-generation businesses, sales often evolves organically. The founder or a principle leads the charge. Over time, a handful of rainmakers build relationships and close deals. This can carry a company to $10M or even $50M or more in revenue.
But then:
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The CEO can no longer wear the sales hat and run the business
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The sales team expands, but the onboarding process doesn’t.
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Marketing generates leads, but the follow-up is spotty.
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CRM data is incomplete, and no one trusts the pipeline report.
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There’s no clarity on what “good” looks like—no KPIs, no scorecards, no sales playbook.
These are the symptoms of a common root issue: the Sales function was never designed for scale. It grew organically, not strategically.
What CEOs Are Asking For
More and more CEOs are recognizing that their sales challenges aren’t about effort—they’re about structure. They’re seeking clarity on roles, expectations, and results. They’re looking for ways to make sales more repeatable and measurable. And they’re ready to evolve from ad-hoc activity to deliberate systems that align teams around a shared strategy and results.
Despite industry or business model, these leaders share one thing: a desire to turn sales from art into science.
What a Scalable Sales Function Looks Like
A modern, scalable sales engine doesn’t kill creativity—it channels it. It gives reps the tools and structure to succeed consistently. That usually includes:
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A clear Ideal Customer Profile (ICP) and value proposition
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Defined sales stages and qualification criteria
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Messaging, scripts, proposals, and decks everyone can use
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KPIs that track not just activity, but outcomes
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Coaching and onboarding programs that ramp new reps faster
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Organizational design, incentives and comp plans aligned with business goals
This is what we call a Sales Playbook—and it’s become foundational to helping our clients unlock consistent growth.
In fact, we recently explored this in our QuickStart Sales Playbook LinkedIn Live series, where we shared why a well-built playbook isn’t just a nice-to-have—it’s essential to aligning your team and closing more deals.
Building your Sales Muscle
We’re seeing more CEOs ask for help not just with strategy, but with execution—because fixing a sales org isn’t about writing a plan. It’s about building muscle.
That’s why we developed the QuickStart: Sales Playbook, a 3-month intensive where a fractional CSO partners with your team to install the structure, tools, and messaging needed to scale and get traction. It’s particularly effective for:
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Companies rebuilding or launching a sales function
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PE-backed firms aiming to drive enterprise value
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Leadership teams needing to align sales and marketing
The real value? It gives the team direction and the CEO clarity—on what’s working, what’s not, and what to do next.
Final Thought: What’s the Risk of not having a scalable Sales function?
The real risk is letting a good team flounder without the structure they need to win. If you’re a CEO watching sales become the bottleneck, the answer may not be more hustle—it’s smarter design.
The good news is that you don’t need to fix everything overnight. In fact, focus will help you move faster. But you do need to stop relying on what used to work—and start building what works now.
