Nearly every senior leadership search we conducted last year identified revenue diversification as a key priority. This isn’t happening in just one sector or only at the CEO level. We’re seeing it across functions—from operations and finance to membership and events—among trade and professional associations, medical societies, federations, and cause-driven nonprofits.
Why the shift? Many organizations still remain heavily dependent on a single revenue source—whether that’s a flagship conference, a cornerstone journal, a long-running certification program, or a concentrated funding base—and every revenue type carries increasing risk.
Journals face open access pressure that’s weakening traditional subscription models. Production costs for conferences are rising while attendance is less predictable. Professional development and certification programs are seeing competition from tech-forward startups offering less expensive and more user-friendly programs. Organizations that rely on a small number of major donors are vulnerable to economic uncertainty.
If the 2008 recession didn’t make the case for diversification, COVID certainly did. And today, with the boom in AI and emerging technologies, the pace of change is accelerating faster than most of us could imagine even five years ago. Organizations are concluding that the risk of staying the same is greater than the risk of change.
The question is no longer whether to diversify, but how, and who can actually lead that work. Particularly for mission-driven organizations built for stability, revenue diversification is as much a hiring challenge as a financial one.
Why the Skills That Sustained Growth Don’t Support Diversification
By definition, successful organizations operate on a model that worked well for a long time. Maybe you had a premier journal or training program with minimal competition in the market. Or your annual conference was the primary (and sometimes the only) place for members to connect and learn. When you have a model that works, you don’t need innovation; you need flawless execution. So you hire people who can sustain and scale a model that’s already working.
But revenue diversification requires an entirely different skill set: curiosity, comfort with ambiguity and uncertainty, data fluency, the willingness to question long-held assumptions, and the ability to design experiments to learn what might work better. Innovation requires ruthless pragmatism to kill off failed experiments and to sunset legacy programs that no longer produce a significant impact.
Innovation is messy, inefficient, and uncertain, and people who value flawless execution find it very uncomfortable.
Where Organizations Go Wrong When Hiring for Revenue Diversification
Mistake #1: Over-Indexing on Industry or Sector Experience
This is the most common mistake we see. Organizations gravitate toward candidates with deep experience in their specific field or sector because it feels safer. The assumption is that they’ll understand your stakeholders and the challenges your industry is facing. While that knowledge is important, you already have people who know your stakeholders and sector. Your new hire will be surrounded by staff, board members, and volunteers with decades of institutional knowledge and constituent relationships.
What you need is someone who can identify what data you need to make decisions, build systems to gather it, analyze your competitive landscape, and distill insights into strategy.
The most impactful leaders understand profit margins, cost structure, and revenue modeling from working in environments that required innovation to survive. It may not matter whether they worked in a nonprofit or have experience in your specific niche, as long as they have varied experience in strategic transformational work.
Mistake #2: Misjudging Organizational Readiness
If you hire a leader to drive revenue diversification but don’t have buy-in from the top, a realistic understanding of what this work requires, and a genuine tolerance for disruption and conflict, you’re setting them up to fail. Before you post the position, get clear on where your organization actually stands:
- What is your current state vs. future state?
- Do you have baseline data? Have you done a needs assessment?
- Will the foundational work be in place before your new leader starts, or will they need to lead that first before driving change?
- How does your organization’s leadership respond when initiatives fail?
- What budget exists for piloting and experimentation?
Then be explicit about your readiness in the position description and during interviews. Strong candidates are assessing you as much as you’re assessing them. They want to know whether your organization is prepared for this work.
How To Interview Leaders Responsible for Revenue Diversification
Look beyond outcomes. A candidate might tell you they launched a new certification program that generated $2M in revenue, but that doesn’t tell you whether they can do it again in your organization. You need to understand their process, their judgment, and whether their success was sustainable.
After a candidate describes a revenue-generating initiative they led, dig deeper with questions like:
- What risks and opportunities did you pay closest attention to? What data did you gather to assess viability?
- Who did you work with and what were everyone’s roles?
- Who were your stakeholders and how did you balance competing interests?
- How did you ensure the right infrastructure—technology, systems, processes—was in place to support growth?
- What metrics did you track to show progress and sustained success over time?
- Describe a tough decision you made during this project. What was challenging and what might you do differently with the benefit of hindsight?
Skilled candidates will walk you through who was involved, what resistance they encountered, and how they navigated it. They can tell you the metrics year over year, not just at launch. Did revenue continue to grow? Did participation stabilize or increase over multiple cycles?
For example, a candidate who launched a new education program should be able to tell you that it generated revenue in year one, how they sustained growth in years two and three, how they adjusted based on learner feedback, and how they improved infrastructure to meet demand.
Red Flags To Listen For
- Setup without follow-through. You want a candidate who has seen this work through multiple cycles. Diversification initiatives need someone who can iterate, not just implement.
- Unsustainable change. A candidate who generated significant revenue but the initiative collapsed after they left. Or an old program they tried to sunset came back because they didn’t build buy-in or transfer ownership.
- Missing infrastructure. They developed new offerings but didn’t ensure the technology, systems, or processes could support scaled growth.
- Lack of attention to relationships. They can’t describe how they managed stakeholder dynamics or what happened during difficult decisions. Revenue diversification often means retiring legacy programs. Leaders need to make change without burning bridges.
Use a Work Sample Interview To Test Candidates’ Revenue Diversification Skills
Work sample testing is one of the most effective tools for evaluating a candidate’s revenue diversification abilities in your specific business context. Following initial interviews, give every finalist a real business challenge they might encounter on the job.
When you discuss the work sample with candidates, listen to their initial approach, then ask strategic follow-up questions. Propose roadblock—budget cuts, board resistance, a key stakeholder who disagrees—and see how they pivot. Strong candidates will be able to adjust their strategy when conditions change.
Rethink Your Approach, Not Just Your Candidate Pool
Organizations that approach hiring for revenue diversification like they’ve approached every other hire end up frustrated. If you hire an optimizer to do an innovator’s job, you risk stalled progress and wasted budget.
Hiring for this type of leader is a search for something fundamentally different, not just a better version of what you already have. That starts with asking different questions, testing different capabilities, and being realistic about whether your organization can support innovation once you hire for it.
Key Takeaways
- Revenue diversification is more than a financial strategy. It’s a leadership and hiring challenge that requires skills different from those needed to maintain or scale existing business models.
- Organizations built for stability often struggle to support diversification because innovation requires comfort with ambiguity, experimentation, and failure.
- Focusing too heavily on deep sector experience can limit diversification efforts; look for leaders who have navigated data-driven innovation and revenue modeling in contexts where it was required for the business to survive.
- Organizational readiness (leadership buy-in, baseline data, risk tolerance, budget for innovation, etc.) is a major factor in the success of any revenue diversification initiative. Even a great hire can fail without the right support.
- Interviews for revenue diversification should probe deeper than surface-level outcomes; explore how candidates assess risk, use data, build infrastructure, and sustain results over time.
- Work sample tests are one of the most effective ways to evaluate whether a candidate can lead revenue diversification in practice.
- If an organization hires an optimizer to do an innovator’s job, diversification efforts are likely to stall. Rethinking hiring strategy is often the first step to changing how you grow.
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