Growth Insights for CEOs

Outsider Insights | The Backup Plan You Don't Have Is Already Costing You
Executive Takeaways
- Commercial team gaps happen for many reasons: someone leaves, someone is underperforming, or the business needs a capability the current team doesn’t have.
- Mid-sized companies tend to run lean, which means there’s rarely a qualified backup ready to step into a critical role.
- The real cost of that gap isn’t the empty seat. Priorities slow, teams lose direction, good people get frustrated, and commercial efforts stall.
- Rushing a permanent hire isn’t always the answer. Fractional resources can keep the business moving while you make the right long-term decision.
- The best time to decide how you’ll handle a critical commercial is before one opens.
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.
Recent Posts

Sales Velocity Model: A Tool for Growth Engine Mechanics
Wed, May 14, 2025 — Most companies deploy a sales “force”. Too often, their combined efforts are not meeting company growth expectations. Most CEOs would like a better growth engine, a larger sales pipeline, and more sales, but they struggle with exactly how to help their sales teams. Busy CEOs combined with people and process related complexities of Sales, often results in companies not being clear on the root cause of their growth engine problems.

Respected Boss? Trusted Coach? Why Sales Managers Need to Be Both
Mon, Apr 7, 2025 — As a front-line sales manager, distinguishing leadership from management responsibilities is critical to a sales team’s culture and success. Distinguishing between the two helps managers be more intentional about developing these very different skill sets. Sales leadership focuses on inspiring and developing people, while sales management concentrates on processes and immediate results. Effective sales professionals must balance both roles.

Sales Terraformance: A Scientific Approach to Sales Growth
Fri, Mar 28, 2025 — Most companies deploy a sales “force.” Too often, this means a bunch of people do things with good intentions, but their combined efforts do not meet company growth expectations. Most CEOs and Founders would like a better salesforce but struggle with how to impact the “art and science” of sales improvement. At Chief Outsiders, we believe more science can help uncover and develop the insights, strategies, and execution required to achieve breakthrough performance.
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Eight Steps to Increase Revenue from Your Existing Customers
Wed, Dec 11, 2024 — Executive Takeaways Growing revenue is cheaper with current customers than new ones. Not all customers deserve the same strategy: segment before you spend. Moving up or down the value chain both open new growth paths. Referrals are the most underused, lowest-cost growth lever you have. There are two ways to grow your business. The first is by acquiring new customers. The second is retaining your current customers and increasing their ongoing revenue stream.

Creating a Strategic Mindset Within Your Sales Organization
Tue, Dec 3, 2024 — By cultivating a strategic mindset within your sales organization, you can drive customer-centric selling practices, create long-term value for the company and its customers, and position your organization for a sustained competitive advantage and growth. A strategic mindset helps align the sales team's activities and priorities with the company's long-term vision, mission, and objectives. This alignment ensures that the sales efforts contribute to the overall success and growth of the organization.

Maximizing Returns with AI-Enabled Selling – A Strategic Blueprint
Mon, Oct 14, 2024 — In the first two blogs of this three-part series, we introduced the concept of AI-enabled selling, the need for an integrated strategy, and a framework for mapping the myriad technologies available to the needs of the sales organization. We learned that the adoption of AI-enabled selling—the sophisticated merger of AI technologies with traditional sales processes—has become instrumental in transforming organizational sales approaches. With this foundation in place, we are in a better position to discuss the payback and chart a path forward that aligns with a company’s highest priorities.

Navigating the AI-Enabled Selling Software Landscape
Thu, Oct 3, 2024 — There was a time not so long ago when the tools-of-the-trade for a salesperson were a Rolodex, a landline phone, and a pair of comfortable shoes. Not anymore. Rolodexes of relationships have been replaced by LinkedIn connections, landline phones by synchronized communication streams, and comfortable shoes by online meetings and note takers, all powered by artificial intelligence.

What is AI-Enabled Selling and Why is it Important?
Tue, Sep 24, 2024 — Salesforce’s “State of Sales” report surveyed 5,500 sales professionals earlier this year. Two findings caught my attention. First, sales reps spend only 30% of their time selling during an average week. Second, 81% of sales teams said they are investing in AI. Of those using AI, 41% believe that they have “fully implemented AI.” The remaining 59% range from having no strategy at all, to tinkering with tools.

What to Do When Your Sales Team Isn’t Delivering – Advice for CEOs
Tue, Jun 11, 2024 — It’s one of the most challenging questions you’ll ever have to ask as a business leader – “why isn’t my sales team delivering the results we need?” Putting a microscope on your team sometimes yields some unpleasant truths, but this exercise is critical when revenue numbers are lacking and the sales pipeline is drying up. Changes need to be made. But before addressing the problem, you need to identify the root causes.