In Part 1 of this series, we examined how AI is reshaping the competencies nonprofits need in their senior philanthropy leaders and why the organizations that adapt fastest will have a decisive fundraising advantage in an increasingly competitive environment. This piece is the harder conversation. Because attracting one of those leaders requires more than a compelling […]
The Leadership Transition Your C-Suite Isn’t Ready For
Most companies don’t fail at leadership transitions because they chose the wrong person. They fail because they defined the wrong job. The volume of transitions is not the problem. The executive succession planning process most scaling companies default to is. C-suite leadership transitions are happening right now at the highest rate in recent memory. CEO […]
How AI Is Reshaping the Demands on Senior Philanthropy Leaders
Nonprofit Philanthropy Leadership Insights The funding crisis facing nonprofits has done something unexpected to the market for nonprofit philanthropy leadership: it has made those leaders more valuable, not less. As federal dollars contract and organizations race to replace lost revenue through individual giving, the Chief Philanthropy Officer, Chief Development Officer, Major Gifts Officer and other […]
Understanding the Different Types of Executive Search
Updated May 2026 | Originally published March 2015 We’re often asked by new potential clients: “How does this work?” And honestly, after more than twenty years in the business, we’re still surprised by how many companies including well-funded, sophisticated ones make the same costly mistakes when it comes to choosing the right executive search model […]
Upskill or Hire? How CEOs Should Build an AI-Ready Leadership Team
The decision framework every CEO and CHRO needs before committing to either path The upskill or hire decision for AI leadership is one of the most consequential and consistently deferred questions in the C-suite right now. Every CEO feels the pressure. The board wants an AI strategy. Competitors are moving. The budget conversation is coming. […]
Should You Trust AI to Evaluate Executive Talent? (And Where It Breaks)
AI executive hiring is no longer an experiment. Whether it is working as intended, and whether it can be trusted at the level of a C-suite decision, are three very different questions. A CEO in San Francisco recently made news for feeding every job interview transcript into ChatGPT before making a final hiring decision. He […]
How to Hire an Executive Who Actually Understands AI
How to hire an AI-fluent executive is a question every CEO and CHRO is asking and almost no one is answering it well. Every week, another board adds “AI fluency” to its executive hiring criteria. Every week, candidates arrive with polished answers about transformation, automation, and competitive advantage. And every week, hiring teams walk away […]
The Pyramid Is Collapsing: What AI and Flat Structures Mean for How You Lead
For decades, the corporate org chart looked the same: a wide base of junior staff, a middle tier of managers, and a narrow band of senior leaders at the top. That pyramid isn’t just being disrupted- it’s being dismantled. The future of middle management has never been more uncertain or more consequential. And the implications […]
The AI Talent War Is Asymmetric. Here’s How Founders Win Anyway.
The leaders who will define your company aren’t browsing job boards. Here’s how to reach them and why your startup has structural advantages some founders never use. You already know the pitch you’re going to get from the other side of the table. Big company. Big brand. Big package. Four-year vest. Good luck. What doesn’t […]
The Right Leader at the Right Moment
Why executive hiring at an inflection point is one of the highest-leverage decisions you will ever make Every company encounters a handful of genuine inflection points, moments when the trajectory of the business can bend sharply upward or collapse inward. How a leadership team navigates those moments is the defining variable. And the people sitting […]