Chief of Staff vs Executive Assistant: Which Hire Will Move Your Business Forward Faster?

For founder-led and scaling businesses, hiring senior support is rarely a transactional decision. It is a strategic inflection point. The question of Chief of Staff vs Executive Assistant typically arises when growth has accelerated, complexity has increased, and the cost of misaligned leadership time is becoming visible. Decisions are heavier. The founder’s role is stretching. Progress feels slower than it should.

What matters most at this stage is clarity.

This is not an either/or decision. A Chief of Staff and an Executive Assistant are fundamentally different roles, designed to solve different problems. Understanding which constraint is limiting your business right now is the key to making the right hire.

The Executive Assistant: Creating Capacity at the Top

At a senior level, an Executive Assistant is not an administrative hire. They are a strategic enabler whose role is to maximise the effectiveness of the leader they support. An experienced Executive Assistant brings structure to complexity. They manage time, priorities, information flow, and often key stakeholder relationships. They anticipate issues before they surface and ensure focus remains on the highest-value work.

Clients typically come to us seeking an Executive Assistant when the founder or senior leader is still deeply embedded in day-to-day decision-making and delivery. The business may be growing well, but progress is being constrained by overload at the top. In these situations, the impact of a high-calibre Executive Assistant is often immediate. By protecting time, improving decision quality, and creating operational rhythm, they unlock headspace and momentum quickly.

For many founder-led businesses, Executive Assistant recruitment is the fastest way to regain control and create space for strategic thinking.

The Chief of Staff: Driving Strategy into Execution

A Chief of Staff operates at a different level. Rather than optimising the leader’s time, a Chief of Staff optimises the organisation’s effectiveness. Their focus is on ensuring that strategy translates into action and that priorities are executed consistently across the business.

This role often includes driving strategic initiatives, aligning senior stakeholders, improving decision-making frameworks, and ensuring accountability across teams. In practice, a Chief of Staff becomes the operational extension of the founder, particularly as the organisation grows.

Clients typically explore Chief of Staff recruitment when the business has reached a point where execution is slowing despite strong leadership. Initiatives stall. Ownership is unclear. Communication fractures across teams.

This role delivers the greatest value once scale and complexity demand a dedicated focus on alignment and follow-through. Hiring a Chief of Staff too early can result in ambiguity. Hiring one too late often means inefficiencies have already taken hold.

Why This Is Not an Either/Or Decision

One of the most common misconceptions we encounter is that a Chief of Staff replaces the need for an Executive Assistant, or that an Executive Assistant should naturally evolve into a Chief of Staff role. In reality, they serve distinct and complementary purposes.

An Executive Assistant optimises the performance of the leader, whereas a Chief of Staff optimises the performance of the organisation.

In high-performing, founder-led businesses, these roles often operate side by side. The Executive Assistant protects focus, clarity, and decision-making at the top. The Chief of Staff ensures strategic priorities are executed across the business.

When these roles are clearly defined and hired intentionally, they form a powerful operating model for scale.

Which Role Do You Need Right Now?

Founders and leadership teams often arrive at this decision intuitively, but a structured lens helps bring clarity.

You are more likely to need an Executive Assistant if:

• Your time is fragmented and dominated by operational detail
• Strategic thinking is consistently pushed aside
• Decisions feel reactive rather than intentional
• You need immediate capacity and focus at the top of the business

You are more likely to need a Chief of Staff if:

• Strategic initiatives are stalling or losing momentum
• Multiple teams or senior stakeholders are misaligned
• Accountability is unclear across the organisation
• Growth has outpaced structure and execution

In some cases, the right answer is not one role, but sequencing. Many businesses benefit from first stabilising leadership capacity through an Executive Assistant, before introducing a Chief of Staff as complexity increases.

This is often where an external perspective is most valuable.

Making the Right Hire

The most important question is not which title feels more senior, but which constraint is currently limiting progress. At Lily Shippen, we work with founders and leadership teams to diagnose this before a search begins. Our role is advisory first. Clarity at this stage protects momentum, budget, and leadership effectiveness.

The right hire can materially accelerate growth. The wrong hire is costly in ways that go far beyond salary.

If you are considering hiring a Chief of Staff or Executive Assistant and want objective, commercially grounded guidance on which role will add the greatest value to your business right now, we would be happy to advise.

Our approach is consultative and confidential. We focus on understanding your business, leadership structure, and growth plans before recommending the right hire.

To discuss your next senior support hire, contact our team