How Chiefs of Staff Are Becoming Internal Entrepreneurs
If you’re a Chief of Staff, you’ve probably noticed the quiet shift happening in your role. You're used to sitting at the crossroads of operations, culture, and strategy—coordinating projects, aligning teams, and being the "go-to" problem solver for leadership. It’s operational, intense, and vital.
But recently, automation and AI tools have stepped in to handle the routine tasks: scheduling, note-taking, task management, and even initial data analysis. For some Chiefs of Staff, this feels unsettling. The obvious question arises: If AI is handling so much, what exactly is my job?
Here’s the good news: your role isn’t shrinking—it’s evolving. As routine operational tasks become increasingly automated, the role of a Chief of Staff is naturally shifting towards something more impactful: internal entrepreneurship.
The Rise of the Chief of Staff as Intrapreneur
"Intrapreneur" might sound trendy, but the idea is straightforward: you're essentially an entrepreneur, but you’re innovating from within your existing organization instead of launching a new startup from scratch. It’s about spotting gaps, testing ideas rapidly, and rallying resources even if formal budgets or teams aren’t clearly defined yet.
Why is this perfect for Chiefs of Staff? Because you’re already set up for it.
Chiefs of Staff occupy a uniquely privileged position. You have insight into every department and initiative. You understand the pain points that different teams face, the bottlenecks that slow things down, and the ideas that—if explored—might unlock significant growth. Yet historically, much of your time was absorbed by keeping the wheels turning, leaving limited space to innovate.
That’s changing. As AI and automation handle mundane tasks, your value shifts from keeping the train running to deciding which new tracks the company should explore.
Imagine an organization wants to test a potential new market segment but doesn’t have the resources to dedicate a full department or product team. A Chief of Staff acting as an internal entrepreneur could quickly prototype and test that market using minimal resources. They might assemble a small, agile team of cross-departmental talent, run quick tests, validate assumptions, and report back with real data on whether the opportunity is worth scaling. All done rapidly, efficiently, and without significant upfront investment.
What Successful Internal Entrepreneurs Actually Do (And Why Chiefs of Staff Are Perfectly Suited)
Chiefs of Staff excel at this intrapreneurial model because you already possess three crucial traits:
1. A Deep Understanding of Organizational Dynamics
You see how teams interact, where communication breaks down, and where collaboration thrives. Entrepreneurs need this skill to align stakeholders quickly and effectively, minimizing friction while maximizing buy-in. Chiefs of Staff already do this instinctively.
2. Resourcefulness and Adaptability
Startups have limited resources and need creative solutions. Similarly, Chiefs of Staff frequently work with constraints—small budgets, tight timelines, limited staff. You’re adept at finding clever, impactful solutions that don't require massive resources, making you the perfect person to experiment and iterate within an existing company.
3. Strategic Perspective and Influence Without Formal Authority
Intrapreneurs rarely have large formal teams. Instead, they rely on influence, trust, and a clear vision. Chiefs of Staff regularly build relationships across departments, motivating teams who don’t report to them. This positions you ideally to lead new, exploratory initiatives that span multiple areas of the business.
In short: internal entrepreneurship is a natural extension of your existing skillset. It’s less a pivot, more a natural evolution.
Why Companies Are Actively Seeking Entrepreneurial Chiefs of Staff
The shift toward internal entrepreneurship isn’t just beneficial for Chiefs of Staff—it’s becoming a priority for leadership teams. Companies at growth-stage levels frequently struggle with the classic innovation paradox: they have more resources than startups, yet remain less agile. They want to test new ideas rapidly but can’t afford to pull entire teams off existing revenue-generating initiatives.
The solution? Empower intrapreneurs. Companies increasingly recognize Chiefs of Staff as strategic investments—not just operational experts, but trusted innovators capable of driving meaningful, cost-effective growth from within.
Forward-thinking CEOs and leadership teams want Chiefs of Staff who actively explore new strategic directions, uncover hidden opportunities, and rapidly validate ideas that could become the company’s future growth engines.
Your Next Step: How to Become an Internal Entrepreneur
If you're a Chief of Staff looking to shift toward an intrapreneurial mindset, consider this your invitation. Here’s how you can start:
Identify a "Low-Hanging Fruit" Opportunity: Look around. What ideas have lingered without action? What gaps are leaders aware of, but hesitant to prioritize? Start small—pick something feasible yet impactful.
Run Rapid Experiments: Don’t ask for huge budgets or dedicated staff right away. Prototype, test, and iterate your idea quickly, cheaply, and efficiently. Demonstrate value fast to gain support.
Tell the Story: Internal entrepreneurs know how to pitch. Communicate clearly how your initiative aligns with broader company goals. Highlight your experiments’ results transparently, whether successful or not. This builds trust and future support.
Coaching to Unlock Your Potential as a Chief-of-Staff Intrapreneur
For many Chiefs of Staff, the transition to internal entrepreneurship is exciting but uncertain. Coaching can clarify your unique intrapreneurial strengths, help identify high-leverage opportunities, and guide you through experimentation and execution with confidence.
If you feel the pull to become more than just operational glue—if you're ready to take a meaningful leap toward internal entrepreneurship—I’m here to help. I work closely with Chiefs of Staff who want to evolve, innovate, and become essential strategic partners by leaning into internal entrepreneurship.
Final Thoughts
The Chief of Staff role is evolving—and you have the perfect skillset to lead this change. You’re not losing responsibilities; you’re gaining room to innovate, test, and build. Your next chapter isn’t about managing operational minutiae; it’s about driving your company’s future growth from within.
Ready to make this leap? Let’s chat about unlocking your full intrapreneurial potential.
