Swiss Army Knife needed? - How to choose between a Chief of Staff, Founder’s Associate and Entrepreneur-in-Residence

You’re spinning multiple plates all at once: Hiring, product, investor updates, team issues… And you know you need support. But what support exactly? Someone to manage strategic projects? Someone to execute hands-on tasks? A temporary team member to explore new business lines? You keep hearing about roles like Chief of Staff, Founder’s Associate and Entrepreneur-in-Residence, but which one matches what you need right now?
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These titles often appear interchangeably in job descriptions and organisational charts, especially in early-stage companies. But they represent very different needs, profiles and expectations. Misalignment on what exact role your organisation needs doesn’t just slow you down, it leads to poor fit, frustration and short tenures.

This article breaks down what each role is really about, so you can make an informed decision based on your current priorities, capacity and vision. Getting this clarity early doesn’t just improve hiring outcomes; it ensures you attract the right partner to help carry your business forward.

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Chief of Staff, Founder’s Associate, Entrepreneur-in-Residence: What’s the difference?

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Let’s start with a quick side-by-side to help you see the core differences at a glance:

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All roles in detail

Now that you’ve seen the big-picture comparison, let’s take a closer look at what each of these roles does – and what kind of profile fits best. This section unpacks the nuance, responsibilities and ideal use cases for each.
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Chief of Staff: The founder’s strategic partner

A Chief of Staff (CoS) is a mid-level to senior, trusted generalist who amplifies leadership impact by translating vision into action. They clear noise, drive internal alignment and run cross-functional priorities – often behind the scenes.
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Common in Series A+ startups where the founder’s bandwidth is maxed out, CoSs are especially valuable when you’re juggling hiring, strategic initiatives and investor management all at once.
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They’re typically responsible for tasks like:

• Preparing board meetings and investor updates
• Running strategic planning and OKR cycles
• Owning special projects across departments
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Strong CoSs are proactive, analytical and deeply trusted by the founder and leadership team. The role often evolves into a senior leadership position over time.

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Founder’s Associate: High-velocity generalist support

A Founder’s Associate (FA) is a sharp, early-career generalist who works directly with the founder to take tasks off their plate and keep the business moving.
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Ideal for pre-Seed to Series A stages, FAs thrive in high-ambiguity, high-urgency environments. They quickly accomplish tasks without requiring in-depth subject matter expertise.
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Typical tasks include:

• Competitor and market research
• Supporting on strategic projects and managing smaller ones end-to-end
• Coordinating hiring processes
• Organising team offsites or internal ops
• Calendar management, prep for meetings
• Support where needed across the organisation
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A strong FA is highly curious, reliable and solutions-oriented. For many, it’s a launchpad role into operations, product or VC.

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Entrepreneur-in-Residence: Embedded innovation engine

The Entrepreneur-in-Residence (EIR) is a unique role, best described as a blend of an intrapreneur and an explorer. EIRs typically have a high degree of autonomy to validate new product ideas, enter new markets or develop spin-offs.
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The role is often time-bound or project-specific, and may or may not lead to a permanent position. VCs or venture studios back some EIRs, while others are hired internally by startups looking to diversify.
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Common EIR missions:

• Researching and validating new business ideas
• Building MVPs and testing prototypes
• Running internal accelerator or incubator programs
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This role is an excellent fit for individuals with founder experience or those who are deeply entrepreneurial topic experts, seeking a space to build without the pressure of raising money immediately.

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So, which one do you need?

To help you choose the right fit, start by reflecting on a few key questions:

• Do you need strategic leverage or operational relief?
• Is this a permanent role or a temporary boost?
• Do you want someone to manage the day-to-day, keep things on track and coordinate across teams? Or do you need someone to explore and build, taking ownership of new ideas and running with them independently?
• Can you offer structure and mentorship or do you need someone to self-steer?
• What level of seniority and autonomy is realistic in your current setup?
• What is your available budget for the role?

At a glance: a Founder’s Associate helps you scale yourself, a Chief of Staff helps you scale the company and an Entrepreneur-in-Residence helps you explore what’s next.

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Final thought: Scope first, then hire

Hiring the right person starts with defining the right role. Get the scope wrong, and even the most talented candidates will struggle. But if you align expectations, ownership and support structures from the start, you’ll set your new hire (and yourself) up for success.

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👉 Are you looking for entrepreneurial talent to join your team? We have a proven track record of successfully hiring for these roles on behalf of our clients. Feel free to schedule an initial call to see how we could support you.