One of the things I love most about the Financial Leadership Foundations community is seeing finance professionals step into roles that stretch them far beyond what they thought they were ready for.

This interview (see the full video below) with Sam Jons, Finance Director at Organise, is a great example of that.

Sam joined Organise around six months ago as their first senior finance hire, moving from a more traditional corporate background into a fast-growing startup environment. Since then, he’s led investor due diligence, managed a significant cash squeeze, and built credibility with founders in a business growing at pace.

This conversation wasn’t about a polished career plan. It was about learning on the job, backing yourself, and putting the right support around you when the stakes suddenly get much higher.

Finding Finance (Even When It Wasn’t the Original Plan)

Like many finance leaders, Sam didn’t set out to become an accountant from day one.

He originally explored computer science, quickly realised it wasn’t for him, and pivoted hard into economics, maths, and business. With finance in the family, a bookkeeper mum, a controller uncle, and an auditor grandparent, the direction became clearer.

What stood out early on was how pragmatic his decision-making was. Choosing an accounting and finance degree because it had a near-perfect employment rate might not sound glamorous, but it set the tone for how he approaches his career: focus on outcomes, not titles.

Why the Move from Corporate to Startup Happened

Sam spent time at large, well-run organisations like Zebra Technologies and CDW. He learned from strong teams and solid structures.

But over time, his curiosity shifted.

His content diet changed. Podcasts and YouTube moved away from pure finance into business-building and entrepreneurship. He experimented with side hustles, none of which made money, but all of which taught him something.

The move into startups wasn’t a grand plan. It started with a conversation. A friend building a business needed help. That help turned into a role. And that role turned into a full-time position at Organise.

That’s often how these transitions really happen.

The Biggest Shift: From Defined Roles to Bias for Action

When I asked Sam about the biggest difference between corporate life and startup life, the answer wasn’t just speed.

It was bias for action.

In large organisations, roles are defined. Processes exist. Progress often means navigating structure or hierarchy. In startups, nothing moves unless someone makes it move.

As Sam put it, projects don’t exist until you create them. Processes don’t improve unless you build them. And you constantly get pulled into things that sit well outside a traditional finance remit.

That can be overwhelming for some people. For Sam, it was energising.

Knowing When to Get Support

What I found particularly interesting is that Sam reached out for support before he officially started in the role.

He knew the step up was going to be overwhelming. Rather than waiting to struggle, he did what many strong leaders do: he invested in learning early.

He consumed content, found my YouTube channel while actively searching for startup finance guidance, read the book, and joined the FLF programme with a simple question in mind:

“Will this increase our chances of success?”

That mindset matters.

What Changed Over the First Six Months

The last six months were intense.

Sam stepped into:

• Investor due diligence with scattered and poorly owned finances
• A steep learning curve doing things he’d only seen in theory
• A serious cash flow squeeze that required immediate control and judgement

What shifted wasn’t just technical capability. It was confidence.

• Confidence to structure learning.
• Confidence to prioritise properly.
• Confidence to become the person founders defer to when decisions are made.

That trust doesn’t come from knowing everything. It comes from being willing to learn, ask the right questions, and show up consistently.

A Career Lesson Worth Highlighting

One of the most important things Sam said was this:

You don’t have to believe you can already do the job. You just have to believe you can learn how to do it.

That’s a critical distinction for new Heads of Finance and first-time Finance Directors.

No one expects you to have all the answers. What matters is your ability to find them.

Advice for First-Time Finance Leaders in Startups

Sam’s advice to others stepping into similar roles was refreshingly grounded:

• Trust your gut, even when you’re inexperienced
• Don’t do it alone – pressure-test your thinking
• Protect your time as soon as your title changes
• Focus on the biggest drivers in the P&L, not the noise
• Look after yourself, because there’s often no one else to step in

That last point is especially important. When you’re the only senior finance person, resilience and sustainability matter just as much as technical skill.

Why Stories Like This Matter

Sam’s journey isn’t exceptional because it’s perfect.

It’s exceptional because it’s honest.

This is what stepping into finance leadership in a startup actually looks like: uncertainty, fast learning, responsibility, and growth that happens in real time.

For anyone considering a move into a Head of Finance or Finance Director role in a growing business, this is the reality to prepare for – and the opportunity to embrace.

INTERVIEW

Want to become a confident, strategic finance leader in a startup within the next 12 months? 

Here’s your plan:

1. Subscribe to my YouTube channel and Newsletter for weekly practical tips and real talk about startup finance leadership.
2. Read my book Financial Leadership Fundamentals to get clear on what’s expected of you and how to show up as a leader.
3. Join the Financial Leadership Fundamentals course to fast-track your growth with structure, support, and strategy that works in the real world.