Growth Insights for CEOs

Winning the Fraud and Cybersecurity Race: A Go-to-Market Blueprint for Competitive Edge
Fraud and cybercrime have become a systemic, trillion-dollar drag on the global economy—but the fight to turn the curve is more than a market opportunity.
Over the past few years, I have worked alongside cybersecurity and fraud-management teams in government, banking, and payments, and nothing is more satisfying than seeing a new solution stop a romance scam or prevent a pensioner from losing their life savings.
Recent Posts

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.

Eight Steps to Increase Revenue from Your Existing Customers
Wed, Dec 11, 2024 — 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. Many companies focus their strategic marketing initiatives on finding new markets, new customers, and new applications for their current product offerings. While this focus is essential, many companies lose sight of their best growth opportunities … their current customers. Current customers allow you to grow your revenue without the increased costs associated with new client acquisition activities.
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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.

The Art of the Proposal: Do’s & Don’ts
Tue, May 7, 2024 — CEOs often struggle with why their sales team doesn’t close more deals. A common reason why deals don’t close is the proposal is not being presented in a way that communicates the most value to the prospect. Worse, the salesperson is having trouble getting feedback from the prospect regarding the proposal's status and, therefore, keeps it on their forecast for a ridiculous amount of time. This article will provide a way to ensure your team creates the most value for your product and service, enabling your company to win more deals and increase revenue.