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

Winter is Coming: How Economically Healthy Are You?
Tue, Jul 18, 2023 — If you are a fan of the hit show “Game of Thrones,” you’ll appreciate where I’m coming from: The ominous pronouncement, "Winter is Coming," always managed to capture my attention since I could see through the fictional seasonal meaning it foretold and apply it to events in everyday life. The first time I heard those words, I couldn't help but feel a sense of foreboding. But as time went on, winter never actually arrived in Westeros. A similar mindset has taken hold in the U.S. business world, where we have been hearing for the past two years that we are in a recession -- when in reality, we are not and have not been.

You Might Hit Two
Mon, Jul 17, 2023 — This post is briefer than my usual, with two quick topics vs. one longer theme. 1. Aim “There’s this thing in quail hunting… if a dozen jump and you shoot at the flock, you don’t hit [diddly squat]." “But if you pick a quail, you might hit two.” Hunting expert Steven Rinella Quoted in the Wall Street Journal, 11/28/20

The CEO Mindset: Resolving Sales Performance Challenges | Part 5
Fri, Jul 14, 2023 — Part 5: Moving Your KPI Levers Into Alignment Managing a sales team can be a lonely job these days. Just a few years ago, the energy in a typical sales office was positively electric. The office reverberated with the sound of ringing phones, demonstrations, strategy sessions, pipeline reviews, and the clanging of the sales bell after a deal was closed.
Stay up-to-date with the latest from Chief Outsiders

CEOs: The 7 C's of Hiring Fractional Executives
Wed, Jul 5, 2023 — Since Christopher McKenna signaled the rise of ‘The World’s Newest Profession’ by publishing his book in 2006, the trend towards hiring and deploying management consultants has only been on the rise. One of the newest categories of management consulting is the Fractional Executive. But how does a CEO go about selecting one? Surely it’s not the same process and set of qualities you’d look for in an executive hire?

The CEO Mindset: Resolving Sales Performance Challenges | Part 4
Mon, Jul 3, 2023 — Part 4: Is Your Sales Process Supporting Revenue Growth? At the dinner table, you tend to get immediate feedback when the recipe of the dish being served is not quite perfected. In the business world, where the steaks….er….stakes are higher, it is no less important to have a plan which appropriately combines the ingredients for world-class success.

Brand Confusion Won’t Work, Even if it’s Intentional
Fri, Jun 23, 2023 — On June 22, 2023, I read an article in the Wall Street Journal about “the H-bomb,” which I learned refers to mentioning that you are a student at or an alumnus of Harvard University. Harvard College’s dean, in a Crimson (the campus newspaper) article where he was asked to give a word of advice to seniors, decided that the best use of this opportunity was to say “Don’t gratuitously drop the H-bomb.”

The CEO Mindset: Resolving Sales Performance Challenges | Part 3
Fri, Jun 23, 2023 — Part 3: Technology Platforms for the Win The market for sales enablement platforms has never been more robust. As companies like yours clamor for clients, revenue, and growth, they’re showering billions on the latest technology tools to help get them there. In fact, a recent report projects that the global market for sales enablement tech will grow at a 15 percent rate over the next five years, topping $9 billion by 2028.

The CEO Mindset: Resolving Sales Performance Challenges | Part 2
Thu, Jun 15, 2023 — Part 2: Finding the Right Talent for the Game Here today, gone tomorrow: Did you know that the average tenure of a sales professional is just about a year and a half? It’s a mind-blowing statistic that is, on the surface, an indicator of the rigors of a sales role, in any market segment.

The Rise of Purpose-Driven Marketing: Connecting with Generations Through Authenticity
Tue, Jun 13, 2023 — By: Paul Sparrow and Philippe Harousseau It was a watershed moment for consumer advertising, with shock waves that are still being felt today – the 2004 launch of the Dove Campaign for Real Beauty. The groundbreaking marketing initiative challenged more than traditional beauty standards – it challenged the conventions of advertising at its core. Eschewing airbrushes and retouching, the personal care brand presented women of various sizes, ages, and ethnicities – without makeup, and without prejudice.