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

The SaaS Marketing Playbook, Part 4 | Getting Sales and Marketing on the Same Page
Wed, Jun 2, 2021 — Of the things that are aligned in our life — the stars, automobiles, our spine, and the universe — there’s one area where such alignment is elusive – and, by extension, costly. If you have ever tried to align your sales and marketing departments, you likely already have experienced how vexing this can be. In my experience, sales and marketing alignment will never be easy. Why not? Three immediate reasons come to mind: 1) Marketing is from Mars and Sales is from Venus, 2) The question of pipeline ownership, and 3) The targets for sales never get lower, and they need to take it out on someone.

The SaaS Marketing Playbook, Part 3 | The SaaS Metrics That Matter
Thu, May 20, 2021 — Are your marketing activities generating a thimbleful of leads, or are they gushing MQLs like a firehose? And, can you directly attribute revenues to specific marketing strategies, or are you just casting proverbial darts at the proverbial dartboard? In my years as a marketing leader, I’ve heard C-suite executives bemoan the efficacy of their marketing activities – based on nothing but gut feel. They alleged that marketing is a black box, or that you cannot effectively measure the effectiveness of your activities.

The SaaS Marketing Playbook, Part 2 | Demand Generation Like a Boss
Thu, Apr 1, 2021 — Have you ever tried fishing without a hook? Needless to say, this very peaceful outing will quickly turn frustrating without a way to bait your line to reel them in. Some would argue that if you were just going to watch the fish swim by, you might have had a better time at an aquarium! Consider this parable within your company – you may have a fantastic brand, and a good sense of what you think makes you unique, but without a way to grab the attention of the consumers swimming by, you might in fact go hungry.
Stay up-to-date with the latest from Chief Outsiders

The SaaS Marketing Playbook Part 1 | Positioning: Finding Your Purple Cow in the Herd
Mon, Feb 22, 2021 — Most marketers may not think they have anything in common with cattle ranchers, but it requires a trip to the Old West to fully understand the history of branding – a term which has significance for both. The National Cowboy Museum explains that branding, in the old days, “provided a way for ranchers to stake their claim on cattle and other livestock, while deterring theft from rustlers.”