Every nonprofit board in the middle of a CEO search eventually says some version of the same sentence: “We need someone who can steer us through a fast-changing technology landscape. Maybe an outside perspective is what we need.” Then one of two things happens. The board passes on its strongest crossover finalist because “they don’t […]
The Founding Team Reckoning: When to Replace, Reshape, or Keep Your Early Leaders
Most conversations about executive mis-hires focus on the outsider you brought in and got wrong. This one is about the insider you got right, the founding VP who built your company from nothing, and the much harder question of whether they’re still the right person for what comes next. Research on founder turnover offers a […]
What AI Fluency Is Worth in the Nonprofit CDO Market in 2026
Boards keep asking what a competitive offer looks like this year. The honest answer: it depends less on the org chart than on whether your candidate can operate the technology stack the best development organizations now run on. In an earlier piece in this series, we made the case that AI fluency has become a […]
The Wall They Didn’t Model
Why Data Center Opposition Is the AI Infrastructure Risk Most Boards Haven’t Modeled Early Enough In September 2025, Google withdrew a contested data center rezoning proposal in Franklin Township, outside Indianapolis, days before the city-county council was expected to vote it down. Months of organized resident opposition had turned what should have been a routine […]
What AI-Driven Agency Restructuring Means for Senior Leadership
Old Pyramid, New Barbell The agency org chart is being redrawn, and not in the way most predictions expected. For decades, the agency model ran on a pyramid: senior leadership at the top, a wide layer of mid-level executors in the middle, and an even wider base of junior staff grinding through drafts, research, and […]
Building AI-Native Teams
Why the Org Chart Matters More Than the Tech Stack Boards and CEOs at the largest technology companies are now being forced to ask, after the fact, who is accountable when an AI infrastructure bet does not deliver. Oracle found out the hard way when its credit rating dropped and a Wisconsin data center suddenly […]
Hiring at a Pivotal Moment: What a Nonprofit Can’t Afford to Get Wrong
Why nonprofit executive hiring during a crisis, funding shift, or political inflection point deserves a different kind of process, and a different kind of urgency Every mission-driven organization eventually reaches a moment when the ground shifts. A funding source disappears overnight. A regulatory or political environment turns hostile. A founder or long-tenured leader departs at […]
The AI Infrastructure Trap
Why the Companies That Bet Biggest on AI Infrastructure Strategy Are Struggling Most In 2025, Oracle signed a $300 billion computing contract with OpenAI, positioning itself as a primary infrastructure provider for the next phase of artificial intelligence. To fund the buildout, the company cut approximately 21,000 employees, roughly 13% of its workforce. The bet […]
The Board’s New Fundraising Mandate: What Governance Looks Like in the Age of AI
Passive nonprofit board membership is fading. In 2026, trustees are being asked to lead through technology, uncertainty, and a fundraising environment that rewards institutions that govern boldly. In Part 1 of this series, we examined how AI is reshaping the competencies nonprofits need in their senior philanthropy leaders. In Part 2, we turned to the […]
The Dual Trap
How AI Layoffs and Token Shock Are Defining the CFO’s AI Workforce Strategy in 2026 At an enterprise event in early June 2026, OpenAI CEO Sam Altman acknowledged something that caught corporate America mid-sip: cost management has become the second most common complaint he hears from enterprise customers. A meme was circulating in boardrooms. It […]