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The Chief Outsider
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Recent Posts
Is Your Contracting Business Growing on Purpose, or on Luck?
Most successful subs know their operations cold. You know your backlog, which jobs are on schedule, where labor is tight, and which estimates are due this week.
Most of you also don’t have a sales department. Business development belongs to the owner and the project managers who are already running projects, so growth work happens in whatever time is left over.
Stop Buying AI Tools. Start Asking This Question First.
Fri, Sep 18, 2026 — Most CEOs start their AI planning in the wrong place. They start with a tool. A demo catches their eye, a peer recommends a platform, or a vendor makes a compelling pitch, and suddenly the conversation is about which AI product to buy instead of what the business actually needs it to do.
The 90-Day GTM Transformation Roadmap: Building the GTM Operating Model While Running the Business
Thu, Aug 6, 2026 — Executive Takeaways The CEO must be the architect and champion of the GTM model — not its operator. Only the CEO has the cross-functional authority to make a unified GTM model stick. If the model only works when you're in the room, it's not a system. When it's working, your calendar proves it.
The CEO's Role as Champion of the Unified GTM Operating Model
Tue, May 26, 2026 — Executive Takeaways The CEO must be the architect and champion of the GTM model — not its operator. Only the CEO has the cross-functional authority to make a unified GTM model stick. If the model only works when you're in the room, it's not a system. When it's working, your calendar proves it.
Stop Hosting Alignment Meetings and Start Building a Unified GTM Operating Model
Wed, May 6, 2026 — Executive Takeaways You can't meeting your way out of a system design problem. Alignment meetings are reactive, CEO-dependent, and fix symptoms — not root causes. A unified GTM Operating Model creates alignment by design, not by force. When the system works, the CEO stops mediating and starts leading.
Pipeline Integrity: How Hidden Revenue Leaks Sabotage Growth
Tue, Apr 7, 2026 — Executive Takeaways A pipeline that looks healthy can still be losing 15–25% of achievable revenue. When teams define MQLs, SQLs, and pipeline stages differently, every other fix fails. Work backwards from your revenue target using conversion rates to find and close the gaps. A one-time diagnostic fades without the right recurring reviews and accountability rhythms.
Go-To-Market Cultural Alignment: The Invisible Variable in U.S. Expansion
Fri, Mar 13, 2026 — Many companies that find success outside the United States have one thing in common: the need to succeed in the U.S. market. That is not complicated or surprising. The United States is the largest economy in the world and, in many categories, the single biggest available market. World Bank data clearly shows the scale of the U.S. economy relative to most global markets. For companies in high-tech, scientific, medical, industrial, and systems integration sectors, the U.S. is not just attractive. It is strategic. Company leaders want to grow. The U.S. is where they look. They are not wrong.
Turning Competing Revenue Team Truths into Market Insight
Tue, Mar 10, 2026 — Executive Takeaways Sales, Marketing, and Customer Success each see different parts of the market. Conflicting perspectives usually reflect incomplete insight, not poor execution. Cross-functional pipeline, win/loss, and customer data turn friction into insight. A unified GTM operating model aligns teams around shared market truth.
Why the CEO-Led Growth Model Breaks at Scale
Tue, Feb 10, 2026 — Series Overview As companies grow, GTM breakdowns rarely show up as sudden failures. They emerge as friction. Progress slows, pipelines become less predictable, and confidence in forecasts declines, even as teams work harder and act with good intent. Written from both the marketing and sales lens, this six-part series, Building a Unified GTM Operating Model, explores why scale exposes weaknesses in informal GTM systems and how an intentional operating model restores clarity, alignment, and scalable growth. Executive Takeaways CEO-led, informal GTM models break predictably as scale introduces complexity. Early GTM failure shows up as friction, not collapse. Sales–marketing misalignment is a structural issue, not a performance problem. A unified GTM operating model is required to restore growth, confidence, and value.
What Can Chester Cheetah Tell You About Your Brand? Part Two
Fri, Aug 1, 2025 — We’ve already discussed how to define a brand in part one. Now, we are going to explore why the C-suite should care about its brand at all. It’s not just numbers, although that certainly is the end game. Remember that brand is the business. Like the business, brand is about being effective, meaning carving a position with a market that is highly productive financially and competitively, and efficient, meaning serving the market in as cost-efficient manner as possible. Brand helps maximize and expand return on investment.