Growth Insights for CEOs

Outsider Insights | From Hustle to System: Why More CEOs Are Rebuilding Their Sales Function
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.
Recent Posts

What Marketing and Sales Executives Can Learn from Each Other
Fri, Mar 28, 2025 — In too many organizations, marketing and sales operate in silos—sometimes friendly, sometimes not. But in today’s fast-moving business landscape, the best-performing companies know that the relationship between all revenue functions – typically the Chief Marketing Officer (CMO) and Chief Sales Officer (CSO) - is not just important. It’s mission-critical.

Top 10 Digital Marketing Missteps
Thu, Aug 1, 2024 — Today digital often seems like the easy way to expand a company’s prospect and lead pool. After all, it takes just minutes to set up an ad account on Google or Facebook. Then you’re good to go, right? Not necessarily. In reality, it’s not as easy as many people think. Marketers are often under intense pressure to get campaigns to work without adequate leadership support or understanding as to how to successfully test digital channels. Others hire agencies without clear knowledge of the strategies and tactics required to drive success and therefore have difficulty holding their agencies accountable.

The Benefits of a Unified Sales and Marketing Strategy
Mon, Apr 22, 2024 — It used to be that companies could achieve growth by simply focusing on sales or having sales and advertising be complementary marketing tactics. But today, macro and micro pressures along with evolving landscapes across industries have resulted in a more competitive landscape. Tools like artificial intelligence (AI) and machine learning (ML) provide a level of sophistication, and these tools can help business leaders bridge strategies and tactics across different business units.
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Beyond Lead Gen: How CEOs Can Leverage Marketing for Sales Performance
Wed, Mar 27, 2024 — In today's competitive business environment, a highly skilled and empowered sales force is essential for driving revenue growth. However, the effectiveness of sales training alone is limited without consistent support and reinforcement. This is where the collaboration between the sales and marketing departments becomes crucial. It's imperative to recognize that marketing and sales are not isolated functions but interconnected components of the business success equation.

Meshing the Growth Gears for Sales and Marketing Success
Thu, Apr 20, 2023 — Why do the Marketing and Sales departments always have to be at odds, blaming each other for poor results? That’s the way it is in so many businesses. But it doesn’t have to be. As a company leader, you just want them to work together and get more sales, right? When the two symbiotic functions are working properly, they mesh like gears - Growth Gears - cranking out more sales power than either can produce separately. Take a brief ride with me to explore a model for making this work.

What Every Midmarket CEO Should Know About Sales Enablement Tools
Mon, Feb 20, 2023 — What are sales enablement tools and why should I care? We are hearing more and more today about the rise of Sales Enablement tools, many AI driven, that accelerate and enhance the Sales Team’s customer outreach. What exactly are Sales enablement tools? Sales enablement refers to technology and related applications that are designed to help your Sales Team do their job more efficiently. It’s more than just call tracking, these tools educate and coach your Sales team making them much more effective in real time. Most integrate into your existing CRM solution while others can stand alone. Through apps, they can facilitate an automatic linkage between your other Marketing and Sales tools, providing visibility into your KPIs and strategies. With 43% of B2B buyers reporting to Gartner that they prefer a “seller-free” experience, Sales Enablement tools are becoming a necessity in the modern Sales Organization for B2B and B2C sellers.

Developing a Sales Methodology for Growth
Mon, Feb 13, 2023 — Sales methodology provides the framework for how different steps in your sales process are carried out in the pursuit of sales development, customer success, and revenue growth. There are countless sales methodologies, and many are very similar or built around the same concept. In Spin Selling, way back in 1980, Neil Rackham looked at the differences between highly successful salespeople and those who were underperforming. He showed that the successful sales reps asked higher quality questions and built a methodology around this evidence.

Conduct a Sales Assessment to Exponentially Improve Execution
Mon, Feb 6, 2023 — As a CEO, you’re tasked with improving your company’s bottom line. You and your leadership team may have a good handle on your marketing strategy, but prior to moving forward with that strategy, it’s a good idea to conduct a sales assessment to ensure your sales team can execute flawlessly. What’s at stake? A lot. One study indicates that more than two-thirds of lost sales are a result of flawed sales methodologies.

CEO Go-To-Market Warning: Avoid the Blind Spots That Cause Products to Miss the Mark | Part 5
Thu, Feb 2, 2023 — Part 5: Only Teamwork Can Make the Dream Work We have become a nation of isolation. COVID-19 taught everyone how to use technology to carry on safely. Though Zoom, Teams, and other tools have made communication more efficient, we’ve never felt more distant from our colleagues. Through this “together, but apart” mindset, many businesses feel pressured to enable remote work and grant greater autonomy. As a CEO trying to manage in this environment, it’s tempting -- in the spirit of efficiency – to let everyone stay focused on their “swim lane” and not encourage complex collaboration between divisions.