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.
Gartner, McKinsey, and BCG Analysis on Rebuilding Sales Function
When looking at the current landscape of businesses, it is evident that the traditional approach to sales is no longer sufficient to meet the demands of a rapidly evolving market. Gartner, McKinsey, and BCG have all conducted extensive research on the topic, highlighting the need for companies to shift from a hustle-driven sales model to a systematic and scalable approach.
Market Trends and Insights
Gartner’s analysis reveals that companies that fail to adapt their sales functions to align with their growth trajectory often face stagnation and missed opportunities. McKinsey’s research emphasizes the importance of structured frameworks in driving sales effectiveness and efficiency. BCG’s findings further support the notion that a well-designed sales playbook is essential for sustainable growth.
Actionable Recommendations
Based on the insights provided by Gartner, McKinsey, and BCG, here are some actionable recommendations for CEOs looking to rebuild their sales function:
- Conduct a comprehensive assessment of your current sales processes and identify areas of inefficiency.
- Implement a clear Ideal Customer Profile (ICP) and value proposition to guide your sales efforts.
- Develop defined sales stages and qualification criteria to streamline the sales process.
- Invest in coaching and onboarding programs to ramp up new sales reps faster.
- Align organizational design, incentives, and compensation plans with your business goals to drive performance.
Organizational Impact
The organizational impact of rebuilding the sales function according to the insights provided by Gartner, McKinsey, and BCG can be profound. By transforming sales from an art into a science, companies can achieve greater consistency, efficiency, and scalability in their revenue generation efforts. This strategic shift not only enhances sales performance but also drives overall business growth and competitiveness.
FAQ
- Q: How long does it typically take to rebuild a sales function?
- A: The timeline for rebuilding a sales function can vary depending on the size and complexity of the organization. However, with a focused and structured approach, significant improvements can be achieved within a few months.
- Q: What role does technology play in optimizing sales processes?
- A: Technology plays a crucial role in streamlining sales processes, enabling data-driven decision-making, and enhancing sales team productivity. Implementing the right sales tools and CRM systems can greatly facilitate the rebuilding of a scalable sales function.
- Q: How can CEOs ensure successful implementation of a new sales playbook?
- A: CEOs can ensure successful implementation by actively championing the initiative, providing necessary resources and support, and fostering a culture of continuous improvement and learning within the sales organization.
Conclusion
In conclusion, the insights provided by Gartner, McKinsey, and BCG underscore the critical importance of rebuilding the sales function to drive sustainable growth and competitive advantage. By adopting a systematic and scalable approach to sales, companies can overcome the challenges of inconsistent results, unclear accountability, and limited scalability. With the right strategies and frameworks in place, CEOs can transform their sales function from a potential bottleneck into a strategic asset that propels business success.
