Growth Insights for CEOs

When the Founder Is the Rainmaker: How to Scale Without Losing the Spark
In many founder-led businesses, the founder isn’t just the leader—they’re also the best (and often only) rainmaker. They land the big deals. They have the trusted relationships. They know the pitch inside and out because they are the pitch.
It works—until it doesn’t.
As the business grows, this model creates a bottleneck. Every new opportunity depends on one and only person. And it’s the same person every time. But there’s a downside. When that person is also responsible for running the business, mentoring the team, and shaping the vision, something eventually gives.
Recent Posts

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.

How to Use ABM to Drive Revenue Growth and ROI: Part 2
Tue, Feb 14, 2023 — By: Carol Eversen and Jeff Loeb Part 2 - Orchestration and Personalization In part 1 of our four-part ABM blog series we shared the core pillars of an ABM program, highlighted the goals and strategies you should consider, and provided guidance about selecting your target accounts and building your Ideal Customer Profile. In part two we explore the core tenet of every successful ABM initiative – orchestration of activities across sales, marketing, and customer success teams.

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.
Stay up-to-date with the latest from Chief Outsiders

How to Use Positioning to Own Your Market
Thu, Feb 9, 2023 — Become a big fish in your pond In my previous blog, “What Tech CEOs Get Wrong About Positioning,” we introduced the concept of market positioning – and specifically, how it helps your customers connect the dots between their needs and your product or service. Of all the marketing strategy lessons we at Chief Outsiders share with founders and business leaders like yourself, positioning ranks among the most critical. It truly is a difference-maker for businesses that wish to become the leader of the pack -- to become, in fishing parlance, the big fish in your pond.

How to Use ABM to Drive Revenue Growth and ROI
Tue, Feb 7, 2023 — By: Carol Eversen and Jeff Loeb As fractional CMOs with deep experience implementing ABM across many B2B companies, we see a pattern emerging: business leaders have very different perspectives about what it takes to implement ABM and how to get started. And most opinions seem to be informed by solution vendors rather than defined by the business challenges at hand. This series of blog posts will guide you through the core pillars of ABM, when ABM should be used and with what approach, and share best practices to get started on a successful ABM journey. You’ll learn about the strategies to consider, the enabling technologies to prioritize, how to measure ABM efforts effectively, and how to get started and reduce risks.

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.

The Recipe for Revenue Success: Sales and Marketing Alignment
Tue, Jan 31, 2023 — As someone who loves to cook, today I am reprising a popular recipe – bringing back a post from the recent past that is ever more relevant today. It’s a tried-and-true concoction that can help you serve up a successful lead generation program. I marvel at the fact that CEOs continue to be disappointed by their marketing outcomes. In fact, 70 percent cite that marketing isn’t delivering for them as expected. Art Saxby, Chief Outsiders CEO, has expertly covered the difference between Sales and Marketing in his blog. I suggest you read it to make sure you have a baseline of understanding, and greater clarity, about the distinction between the two disciplines.

CEO Go-To-Market Warning: Avoid the Blind Spots That Cause Products to Miss the Mark | Part 4
Thu, Jan 26, 2023 — Part 4: Mastering Your Channel Strategy If you’ve been with us through the previous blogs in this series, we’ve cautioned you against the go-to-market pitfalls that could cause your company – and its profits – to slide into a deep ravine on the road to riches. We’ve alerted you to be wary of competitive and market forces that will diminish demand, and waved an orange flag against a product-market misfits or differentiation that is not enough to dislodge competition.