Chief of Staff Interview - Rafe Welsh from StoriBoard

So, today we are speaking with Rafe Welsh, Chief of Staff at StoriBoard.

Rob) So Rafe, thanks for your time today. Let’s start with value. What would you say is the value of a Chief of Staff to A) the Principal and B) an organisation? 

Rafe) I work as a Chief of Staff in a small startup, and my value comes primarily from supporting the founder. In a role like this, it's all about being the person who's looking around corners- identifying risks early, keeping everyone aligned on priorities (a difficult task with a strong entrepreneur at the helm), and taking on the major projects that the founder doesn't have capacity for.

From an organisational perspective, the CoS operates across functions and fills the gaps. Because I have visibility across the entire business, I can act as a strategic advisor - connecting the dots between teams, pre-empting issues, and pushing forward initiatives that might otherwise stall. I go from manning our customer service at 11PM, to manually adjusting data for our development team, ordering laptops for new team members to then advising our CEO on our Business Plan/Tech Stack.

In a startup, founders often carry the emotional and operational weight of the business alone. One of the biggest values I bring is sharing that weight. For my founder, Karen, I aim to be a partner who lightens the load—whether that’s through execution or emotional support. My north star is always: how can I make Karen’s life easier and support her in delivering what she needs to?

Rob) With the advent of AI being integrated into business operations, is there anything you have found helpful in your role or initiatives that you have led into the business that has had a force multiplier effect for you, your CEO, or the business? What was the impact?

Rafe) ABSOLUTELY! We’re a team of five, currently in our scaling phase as we head toward raising VC. AI has been a force multiplier for us, especially for the kind of high-effort, low-complexity tasks that used to eat up hours. I truly believe with the use of AI, we will be able to keep a low headcount and still operate like we are a 100 person team.

Personally, I’ve used AI for drafting the base of internal policies, analysing anonymised data to inform business decisions, and even managing personalised comms for our 100+ restaurant and activity partners. It’s transformed how quickly we can move and how professional we can look at our size. What would’ve taken hours now takes minutes, giving us back time to focus on the work that really moves the needle.

Rob) Why did you want to take on a Chief of Staff role? What skills/experiences did you bring to the job that you have leveraged during your time as CoS, and what did you have to learn on the job? 

Rafe) I started out as a Founder’s Associate, which is often seen as a stepping stone into CoS. You’re a generalist who works side-by-side with a founder and acts as a multiplier by picking up whatever needs doing.

My career has been pretty squiggly over the last 8/9 years. An ops manager at a family-run IFA, sales and contracting at a drone company, the first project manager and energy trader at an energy startup that grew from 60 - 400+ team members that also managed a 200 person contact centre operation in South Africa (who knew they were a combo??), a client success in a SaaS Booking company with major brands like Dior, Charlotte Tilbury and LEGO, and then a short stint at a transitioning mental health startup before landing where I am. All these combined, gave me more experience than I realised I had. Implementing new tech solutions, no problem. Operational policies, a breeze. Partnerships, go on then. Manage an offshore team of 200+ agents during a data incident. Where’s my hairline gone?  I had experienced leading or playing a role in numerous areas which made my experience much more valuable than I thought. All of which came from being trusted by CEOs, COOs and Directors to deliver.

What I brought was versatility. I’m not a deep specialist, but I can pick things up quickly and run with them. That adaptability has allowed me to drive big projects and wear multiple hats, something that’s essential in early-stage environments, where the only other person like that is the founder.

That said, most of what I’ve learned has come from this role, especially under the mentorship of Karen - an entrepreneur who has exited three businesses and genuinely changed my trajectory. The biggest lesson? Be okay with failure. Startups are messy. We’ve pivoted multiple times before finding traction. Resilience, self-awareness, and taking feedback without ego have been the tools I’ve sharpened the most here.

Rob) Would you recommend the Chief of Staff role to people looking for a fast-tracked route into a leadership role? If so, what should they do to prepare for the job? If not, please explain. 

Rafe) It can be. But it shouldn’t be seen just as a shortcut to the C-suite. The CoS role is not a "junior COO" role or a guaranteed ticket to exec leadership. It's a unique role in its own right that demands ALOT. In an early stage startup, if you are doing your job right, you are essentially a co-founder and partner.

If you want to become a CoS, go get your hands dirty in early-stage companies. Say yes to ambiguous projects. Be the person who volunteers to solve the problem no one else wants to own. Learn how different parts of a business work and how to communicate effectively. Active listening is a skill lost by most people but can make a world of difference. 

Also, be honest with yourself about whether you want to be a number two. Some of the best CoS operators I’ve met don’t want the spotlight as they thrive in a role that’s about enabling others.

Rob) What are the biggest misconceptions and confusions surrounding the Chief of Staff role in the startup space? 

Rafe) The CoS role is often misunderstood because it looks different at every startup. It’s not just a glorified EA role (and EAs bring massive value in their own right!). A CoS is a strategic sounding board, a trusted operator, and someone who sees the whole chessboard.

People also assume there's a defined playbook, that by following all the theories/frameworks that Google or McKinsey has taught you will work in an early stage startup, but most of the time, you're writing it as you go.

Rob) What is your spiciest take on the COS role that most other people would disagree with? 

Rafe) Controversial but, just because you worked as a consultant or in PE, does not mean you are equipped to work as a CoS in a start-up. You don’t have the same level of resources and you aren’t siloed into a specialisation. They’re overlapping skill sets, but they’re not the same. 

Rob) We talk a lot about AI, but what other major trends do you believe will reshape the Chief of Staff role in the next 3-5 years? Why, and what can Chiefs of Staff be doing or learning to future-proof themselves?

Rafe) As AI eats more of the admin heavy parts of the job, the CoS role is going to get even more strategic. Think of the CoS of the future as a cross-functional operator with the emotional intelligence of a therapist and the execution of a COO.

To future-proof? Build your emotional intelligence. Learn how to be the person your CEO trusts implicitly. AI can do tasks—but it can’t build trust, navigate politics, or sense when your founder is burning out. That’s where your edge will be.

Rob) The Chief of Staff role is notoriously demanding. What does your personal 'operating system' look like? Are there any non-obvious productivity frameworks, communication cadences, or tools you swear by to manage the flow and protect your focus?

Rafe) Honestly, I’ve found that most rigid frameworks fall apart in early-stage startups. Things move too fast, and flexibility always wins over perfection.

That said, I live by a few key principles: always leave things better than you found them, prioritise by impact, Trust who you hire - or don’t hire them, things can be good enough yet have a bigger impact than taking the time to make them perfect and over communicate everything - you’ll never regret letting someone know a task you’ve thought of at 2am. Tools-wise, I love Lucid for diagramming and creating flows to visualise how we are operating.

I also go by, always get to know the person behind the work veneer - I operate 10x better knowing my team's raison d'être (reason for being).

Rob) Beyond alignment meetings, what's one subtle but crucial thing you've found essential for building and maintaining that deep level of trust and effective partnership with your CEO or other leaders?

A10) Treat your CEO like a human first, executive second. Founders carry so much pressure, and sometimes what they need most isn’t a deck or a decision. it’s someone who sees them, listens without judgment, and can say, “I've got this, go take a breather.”

It’s the micro-moments of trust that build the deepest partnerships.

Follow Rafe here and StoriBoard here.