Nibble

What “Being Entrepreneurial” Really Means Inside Big Companies

Written by Nibble | Oct 3, 2025 12:35:11 PM

There's a lot of talk right now about how enterprise procurement teams need "entrepreneurial people" to unlock the benefits of AI. But what does that actually mean? 
From Rosie Bailey, Nibble CEO
 

Last week, I was guest lecturing at London Business School for Jessica Spungin’s class on innovation in large corporations — and, frankly, why big companies are usually crap at it.

I spent 20 years in massive organisations and the last 5 running my own tiny AI company. I now realise I totally underestimated the opportunities I did have to innovate inside big institutions. And I definitely misunderstood what it meant to “be entrepreneurial.”

So, here’s my attempt to set the record straight — and maybe help someone in a large company realise they can make a difference now, before they leave in frustration.

Freedom vs. Scale

For 20 years I worked in banking — first at boutique firm Lazard (5,000 people but it felt smaller), then Morgan Stanley (80,000+ people, US HQ-ed), and finally RBC, a high street banking giant in Canada as well as an investment bank.

Each move made me a smaller cog in a bigger machine. You don’t feel like you can make a difference.

Now, as a founder of an AI company, I have the opposite problem: I can move fast, innovate in a week instead of a year… but my reach is limited by the size of my ecosystem. It’s freedom without scale.

Invisible Impact

Back then, I thought I wasn’t moving the needle. Looking back, I realise even small changes I pushed through had ripple effects I couldn’t see. I suppose its a kind of butterfly effect.

On my last day at RBC, the most junior person on my team surprised me by pulling me into the boardroom. Inside were 20 smiling faces, a huge bunch of flowers, and a card, hand-signed by all the analysts and associates.

Why? For the last 18 months, I’d sat on their advisory committee — helping them approach senior management for more Bloomberg terminals, better late-working perks, and a small pay rise to match the rest of the Street. To me, it was minor in terms of time commitment and not difficult to coach talented people. To them, it changed their quality of life (and for the bank it reduced staff turnover).

And the card? I still have it. (Not the norm in investment banking culture, I’ll be honest.)

In procurement, the same is true: piloting a new supplier or championing a smarter process may feel small compared to a billion-dollar spend. But the ripple effects can transform an organisation and give them confidence to try new things elsewhere or scale its impact.

The Entrepreneurial Mindset Anywhere

When people talk about “entrepreneurship skills,” they often assume it means coming up with radical new ideas. But from where I sit now, that’s only a tiny part of it — and not every entrepreneur is the “big ideas” person anyway (that’s Jamie Ettedgui in my case at Nibble).

The real entrepreneurial mindset looks like this:

  • Grit / resilience — showing up every day, executing piece by piece, not letting setbacks stop you.
  • Risk-taking — in a corporate, that often means asking forgiveness, not permission.
  • Action orientation — just DO it.

Inside a big company, it might feel harder to take risks. But you’re rarely betting the ship — you’re just saying: “Why not try it? What’s the worst that can happen?” And if you show, not tell, you’ve got a far greater chance of success so always try and come up with the minimum viable product version of the idea, show how it works in practise.

Gold Dust in Procurement

I’ve spoken to several CPOs recently who say only a handful of people in their teams thrive in uncertainty, run with new projects, and embrace change. These people are gold dust.

The challenge? Spot them, protect them, and give them space. They’re usually not sitting in innovation labs — they’re buried inside your teams. Empower them, and they’ll deliver outsized impact.

I will be talking more with Andrew Daley about building AI ready teams in the next month or so as part of his new venture. I am excited to both share and learn. We all need to be upskilling ourselves for AI / agents / digital change, tackling it with curiosity and confidence and learning to ask the right questions without fear of being bamboozled by the answers!

Key Takeaways

  • Freedom vs. Scale: Procurement leaders can give teams founder-like agility while keeping corporate reach.
  • Invisible Impact: Don’t underestimate small tweaks — the ripple effect.
  • Entrepreneurial Mindset: It’s less about ideas, more about grit, action, and calculated risk.
  • Gold Dust People: Spot them, back them, and help them thrive.

 

👉 If you’re leading in a large organisation, the best way to capture the upside of AI is centred around giving your entrepreneurial people the oxygen to do their thing.

 
 

Find out more from Nibble's experience negotiating 100,000 times a month here

 

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