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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.
Tariffs and Your Next Chapter | Buying in a Tariff Economy: Smarter, Not Cheaper
Wed, Apr 9, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.
Tariffs and Your Next Chapter | Selling Through Tariffs: Avoiding the Pricing Traps
Tue, Apr 8, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.
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.
Tariffs and Your Next Chapter: Turning Disruption into Go-to-Market Growth
Mon, Apr 7, 2025 — Tariffs have been around for centuries. Commonly used to protect emerging industries or bolster national security, tariffs have evolved beyond trade tools into economic levers that can shift markets overnight. Tariffs have re-entered the conversation for mid-sized business leaders, especially those with global supply chains or international customer bases. But here's the thing: reacting like it’s still 1995 won’t cut it.
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.
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.
Leveraging AI: Is Your Company Future-Ready? | A Roadmap of Eight Essential AI Steps for Success
Mon, Mar 24, 2025 — A BCGX study reveals just 6% of companies have trained 25%+ of their workforce on Gen AI tools, yet 100% will require upskilling within two years. With Accenture projecting AI will augment 40% of work hours and McKinsey forecasting 70% automation of business activities by 2030, the urgency for strategic AI adoption has never been greater.
A Different Perspective on Marginal Cost Pricing
Fri, Mar 7, 2025 — I pulled up behind a Prius at a red light. A sticker on its left rear bumper, in type too small to read unless you were within a car length or two, said: “Sorry for driving so close in front of you.” A different point of view on the tailgaters that clearly bug that vehicle owner!
The AI Revolution: Why SaaS Companies Must Adapt or Become Obsolete
Fri, Mar 7, 2025 — In 2025, AI agents are revolutionizing the SaaS industry, transforming traditional cloud-based applications into dynamic, self-optimizing platforms. For business leaders, this trend represents a seismic shift from FOMO (Fear of Missing Out) to FOBO (Fear of Becoming Obsolete), with the rapid pace of AI adoption and its transformative potential driving noticeable shifts in strategy.