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Outsider Insights | The Backup Plan You Don't Have Is Already Costing You
Outsider Insights
Across Chief Outsiders, we talk to hundreds of CEOs every month. In this series, we explore the trends and challenges we’re hearing from these discussions – and what you can do if you’re facing the same issues in your business.
Where Is Growth Coming From? A Playbook for Mid-Market CEOs
Thu, Jul 2, 2026 — The headlines say one thing. The data says something more nuanced. Here's what mid-market CEOs should actually be paying attention to right now. This two-part series from Chief Outsiders Founder & CEO Art Saxby explores what the data actually shows about CEO confidence, why this moment is different from past disruptions, and where mid-market companies are finding real growth opportunities right now.
Uncertainty Is Real. Opportunity Is Too.
Mon, Jun 15, 2026 — The headlines say one thing. The data says something more nuanced. Here's what mid-market CEOs should actually be paying attention to right now. This two-part series from Chief Outsiders Founder & CEO Art Saxby explores what the data actually shows about CEO confidence, why this moment is different from past disruptions, and where mid-market companies are finding real growth opportunities right now.
Building a Cohesive C-Suite: How to Align Your Executive Team for Success
Fri, Jun 12, 2026 — Executive Takeaways A high-performing C-suite that doesn't function as a team is a hidden growth tax. If your executives describe the strategy differently, that gap shows up in your results. Alignment comes from operating rhythm, not offsites. Better-aligned executives. Same team. Very different results. When CEOs talk about growth, they usually focus on markets, products, and funding. What derails them more often is something closer to home: a strong group of executives that never quite functions as a true team. You feel it in slow decisions, mixed messages to the organization, and initiatives that lose momentum once they leave the last executive meeting.
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.
When to Hire a Fractional CMO vs Full-Time CMO
Tue, May 26, 2026 — Executive Takeaways The distinction between fractional and full-time CMO isn't hours or cost — it's orientation and incentives. Fractional wins in definable contexts: transitions, growth stages, and moments requiring an honest broker. The CEO-CMO trust gap is structural, not personal. Fractional leadership changes the architecture. Full-time is right for large-scale transformation. CEOs must match the model to the moment.
From Loyalty Programs to Leadership: What 20 Years in CRM Taught Me About Organizational Growth
Mon, May 11, 2026 — Executive Takeaways The principles that build customer loyalty work just as well on your best employees and partners. Salary and bonus are table stakes. What keeps top performers are the moments that make them feel like insiders. Internal friction is as damaging as friction in a customer journey — and just as fixable. Generic recognition retains no one. Tailored moves do. Loyalty programs taught many of us how to turn casual buyers into raving fans. My 20 years in CRM and loyalty for brands like Marriott, Amazon, and American Express—and leading a $3B customer platform—taught me something bigger: The same system that keeps customers coming back also keeps your best people from leaving. When growth stalls, most CEOs reach for the usual levers: more demand gen, more recruiting, more channels.
Should I Hire a Fractional CMO?
Fri, May 8, 2026 — Executive Takeaways A full-time CMO can cost $1M in year one — before the first campaign ships. Full-time CMOs optimize for tenure. Fractional CMOs optimize for outcomes. Fractional CMOs bring cross-industry pattern recognition that deepens with every engagement. Fractional leadership wins in specific, definable contexts. The next article maps exactly when.
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.
Marketing Leadership for CEOs: An Executive Guide to Growth
Mon, May 4, 2026 — Executive Takeaways At a certain scale, Marketing stops being a support function and becomes the company's growth system. Everyone has opinions about marketing, which means it rarely gets the disciplined oversight it actually requires. The CEO is uniquely positioned to set clear intent and hold the function accountable. As a connected system, Marketing drives alignment and focus. This blog is part of Chief Outsiders’ Marketing Leadership for CEOs series, an ongoing examination of the critical dimensions of Marketing (the capital “M” is intentional, as you’ll see) that every CEO needs to understand.