One of the clearest signals I’m seeing in the Education / EdTech market right now isn’t showing up on job boards or in LinkedIn announcements. It is happening quietly. We are seeing significant activity around confidential Director, VP and C-level leadership changes, succession conversations and organizations reassessing whether the leadership teams that got them here are the teams they need for the next phase.
That matters.
As we head into Q4, I believe this activity is giving us an early view of how Education and EdTech companies are thinking about 2027. Organizations are not simply adding headcount. They are becoming more deliberate about which leadership capabilities they need, where they need different experience and how each role connects to growth, AI, profitability and customer outcomes.
For CEOs, founders, boards and investors, now is the time to have those conversations.
The Market Is Active, but Companies Are More Selective
The EdTech market is not behaving like a market in which companies are hiring simply because capital is available.
HolonIQ reported that global EdTech venture funding totaled $1 billion in the first half of 2026, down 26% year over year, while deal volume remained relatively stable. Importantly, average deal sizes also contracted. That suggests investors have not stepped away from EdTech, but they are making smaller, more selective investments and placing capital more deliberately. For operators, that reinforces a broader theme we are seeing in the market: growth is still possible, but companies are being asked to prove outcomes, demonstrate ROI and make more disciplined decisions about where they invest, including in leadership and talent. Read HolonIQ’s H1 2026 EdTech funding analysis
Companies are asking harder questions before opening a role. Do we need a CRO, or does the business need a different commercial structure altogether? Does the next CEO need to be an operator, a transformer or a category builder? Is this truly a new role, or should responsibilities be redistributed across the leadership team? Can we merge two roles into one?
Those are much healthier questions than simply asking, “Who can we hire?”
Why So Many Leadership Conversations Are Confidential
Confidential executive hiring can happen for many reasons. There may be an incumbent in place. A board may be considering succession. An organization may be preparing for a transaction, restructuring or new phase of growth that has not been announced publicly.
What stands out to me now is the strategic nature of these conversations.
Organizations are looking ahead rather than simply reacting to an immediate vacancy.
That creates a different leadership discussion. The question becomes less about replacing one person with another and more about determining what the organization will require over the next three to five years.
In confidential situations especially, relationships matter. Many of the executives best suited for these opportunities are not actively looking for a new role. Engaging them requires discretion, credibility and a compelling story about where an organization is headed.
AI Is Changing the Leadership Profile, Not Just the Technology Roadmap
Almost every leadership discussion today eventually reaches AI.
But I think companies need to move beyond asking whether a candidate “understands AI.”
The more useful question is: Can this leader redesign the way the organization works because of AI?
Research from LHH Recruitment Solutions, Inc. and The Adecco Group found that 51% of CHROs say AI has already changed the skills required for certain roles, yet only 37% say their organizations have adjusted job descriptions accordingly. See the 2026 workforce-planning findings from LHH
That gap is showing up in hiring conversations.
AI will influence product strategy, customer experience, sales productivity, organizational design and operating leverage. The strongest 2027 leadership teams will need executives who can determine what technology should do, what people should do and where the combination creates a better business and better outcomes for learners.
What Leaders Should Be Thinking About Before Q4
If you are beginning your 2027 planning now, I would put five talent questions on the leadership agenda.
1. Start with business outcomes, not titles.
Define what must be different by the end of 2027 before deciding which roles you need. Revenue growth, new markets, AI-enabled products, retention, profitability and organizational scale may each require very different leadership profiles.
2. Look critically at the capabilities already around the table.
Workforce planning should include the executive team. Where do you have strength? Where are there gaps? And which roles have evolved enough that yesterday’s job description no longer applies?
This may also be the right time to conduct a McKinsey 9-Box Talent Matrix exercise with your leadership team. Looking at both current performance and future potential can help identify succession priorities, development opportunities and areas where the organization may need to bring in new capabilities for its next stage of growth.
3. Build succession plans before you need them.
Confidential CEO and C-suite work is a reminder that succession should not begin when somebody resigns. Boards and CEOs should understand both their internal bench and the external talent market well before a transition is necessary.
4. Reassess how you evaluate executives.
As roles become broader, instinct becomes less reliable. Structured interviews, role-specific assessments, commercial and cognitive evaluation, performance evidence and deep referencing can give leaders a much clearer picture of future fit than chemistry alone.
5. Give yourself enough time to reach passive talent.
The best candidate may not be applying anywhere. Proactive outreach and thoughtful talent marketing become particularly important when the profile is specialized or the opportunity is confidential.
SHRM’s 2026 research reinforces the broader challenge: lack of qualified candidates and sourcing difficult roles remain top concerns for talent leaders, while securing critical talent has become an increasingly strategic business priority.
What I Expect as We Move Into 2027
I expect the EdTech leadership market to remain active, but I do not expect a return to frantic hiring.
Instead, I believe we will see fewer assumptions and more intentional team design.
There will be continued movement at the C-suite level. AI will force additional role redesign. Consolidation and investment activity will create new leadership needs. And companies will increasingly value executives who can bridge mission and commercial performance, especially leaders who understand the complexities of Education rather than simply applying a traditional technology playbook.
For more than 30 years in Education and EdTech, one pattern has remained remarkably consistent: the organizations that make the strongest leadership decisions tend to begin thinking about talent before the need becomes urgent.
Q4 is the time to do that work.
Key Takeaways
The signals I would carry into 2027 planning are straightforward: confidential senior leadership activity is pointing toward meaningful leadership change; companies are hiring more selectively; AI is changing role requirements faster than many organizations are redesigning jobs; succession and workforce planning belong on the executive agenda; and reaching the strongest leaders requires a proactive, high-touch approach rather than waiting for applicants.
If you’re thinking about how your team needs to evolve or planning for growth we’d welcome a conversation.
