Details
Robert Baker
27th March 2025
Insights
Snakes and Ladders has become a board game of choice for my 5-year-old daughter over the last few months. At the same time as taking yet another pummelling defeat recently, I thought Snakes and Ladders is an excellent metaphor for senior finance leaders progressing their careers to CFO.
The CFO Practice focuses on CFO and Finance Director searches for high-growth and transformational businesses backed by Venture Capital or Private Equity funds. Over the length of my career, I have worked with a broad range of candidates progressing at different speeds and trajectories to becoming CFO. Starting a career in finance is simple, but making the right moves to becoming a CFO in the desired type of business can be much more of a challenge.
Which career progression type are you?
- Type 1: The 100m Sprinter – The first type is the sprinters, who view their career as a 100m race. These candidates are highly motivated to become CFO ASAP, with less concern for the business type, size, or strategic direction.
- Type 2: The Marathon Runner – Type 2 candidates take a more thoughtful approach. They recognise their career is not a sprint but a marathon, often lasting several decades. Type 2 candidates carefully consider the experience necessary to excel as a CFO, typically with a clear career plan detailing the exact progression required to become a CFO, often for mid-market or larger organisations.
- Type 3: The Steeplechaser – While Type 1 and Type 2 sit at opposite ends of the spectrum, most candidates fall somewhere in between, adopting a more agile and adaptable approach to their careers—let’s call them Type 3: The Steeplechaser.
Like a steeplechaser navigating hurdles and water jumps, these candidates understand the skills and experience needed for long-term success. They also recognise that progression isn’t always a straight sprint and doesn’t have to be a structured marathon. They build flexibility into their careers, spotting opportunities to develop their financial leadership within high-growth organisations—even if it means taking a detour to gain crucial experience or seize an opportunity.
They are typically more entrepreneurial and open to unconventional routes with their career on a more vertical or horizontal trajectory depending on their motivations, personal attributes, and ability to spot the right opportunities.
So, can a sideways or downward move be good for your aspirations of becoming CFO?
Yes, absolutely. However, a sideways or downward step must be right for you and something that will help springboard your experience to becoming CFO.
The traditional CFO skillset has always blended financial operations, commercial finance, strategy, and leadership experience. While we see increasing numbers of candidates becoming CFOs moving directly from banking and consulting backgrounds, most still develop a broad range of skills before securing their first board-level position. This is why a finance leader should continually assess their experience against what is required to become CFO.
Type 1 candidates, the 100m sprinters, often find themselves pigeonholed in their careers after becoming Finance Directors or CFOs in smaller, privately owned businesses, as they can find a glass ceiling preventing them from progressing to CFO roles in more significant, listed, or investor-backed organisations, as they are typically used to more simplistic businesses.
That’s why it’s crucial for the Type 3 steeplechasers progressing towards CFO to regularly assess their careers and ensure they are on track to achieve their goal in an organisation with the right mix of scale, complexity, and ownership model.
It’s not out of the question for Type 2 candidates to take a sideways or downward step, especially if their longer-term motivations change. However, detours are less typical due to having a clearly defined career path.
So, what should you do if you’re Number 2 or 3 in finance but lack some of the key skills to become a CFO?
One of the smartest moves a future CFO can make is broadening their skill set beyond pure financial control or commercial finance. However, senior-level exposure and operational environment are also key elements:
Experience
A sideways move into a role with more exposure to commercial decision-making, pricing strategies, or operational efficiency can be a game-changer. It’s not about stepping back—it’s about stepping sideways to gain a more rounded perspective. Those who take this approach are often better equipped to step into a CFO role and confidently navigate the numbers and the broader business landscape.
Exposure
Another key factor is leadership scope and exposure to the senior management team. Moving into a role that provides greater boardroom exposure, direct investor interactions, or significant transformation experience can be the difference between a good CFO and a great one. CFOs in private equity and venture capital-backed businesses are often responsible for leading restructures, M&A, and exit strategies.
Environment
If your career has been in a steady-state business, a sideways or downward move into a more dynamic, change-driven environment, such as venture capital or private equity, could be the best long-term career decision. These experiences, not just the job title, prepare candidates for the right CFO opportunity.
Chris’ story
I have worked with Chris Musgrove for over 20 years, placing him on multiple occasions and partnering with him on recruitment projects. Chris is a Big Four-trained Chartered Accountant and is currently the CFO of a Business Growth Fund-backed business.
In 2015, Chris found his career at a crossroads. He was very much a Type 3 Steeplechaser in a senior commercial finance role working at a high-growth services business but couldn’t see an obvious path to CFO. He recognised that his career lacked hands-on operational finance experience—a skillset highly valued by private equity firms when appointing CFOs into portfolio companies.
Chris took a sideways move in 2016, joining Reevoo, an investor-backed marketing solutions business, as Financial Controller. He saw this as an opportunity to deepen his financial operations experience before climbing the ladder towards CFO.
By 2018, Chris was formally appointed CFO of Reevoo, and in 2021, he successfully led the sale process to Feefo. Today, Chris is the CFO of Techspert, an AI-driven technology platform specialising in healthcare and life sciences. He has played a pivotal role in scaling the business, expanding into the US, and delivering projects across 100+ global locations.
Final thoughts
While a sideways or downward move can be a positive career step, it’s not right for every scenario. Sometimes, focusing on developing your experience internally and simply asking for increased responsibilities can do wonders for your career. I would always advise candidates considering their careers to keep an open line of communication with their CFO, CEO, and other key board members before seeking external opportunities.
Here are some key factors to consider before making the leap:
- Lack of development opportunities – Does your current role or company provide a clear path to broadening your skill set and progressing you closer to CFO?
- Framing the move strategically – Hiring managers and investors may view sideways or downward moves with scepticism unless you can clearly articulate the strategic rationale behind the move.
- Short-term financial gain – If the move is driven purely by salary rather than long-term career growth, this could be perceived negatively by future hiring managers and could impact your future progression.
- Assess the role’s value – Will the role provide significant career development and new responsibilities such as commercial finance, investor relations, M&A, or transformation projects? If so, it could be a strategic move.
Right, time for me to return to my most important opponent: a 5-year-old who’s worryingly good at Snakes and Ladders. If only career progression came with a dice roll and a smile.
The CFO Practice
At The CFO Practice, we understand that no two journeys to CFO are the same. Whether your path involves sprints, marathons, steeplechases, or the occasional sideways move. We work with high-growth, investor-backed businesses across the UK to build exceptional senior finance teams and help finance leaders unlock the experience and opportunities needed to reach CFO. You can find out more about how The CFO Practice support this through our Executive Search services.
If you’re considering your next move or looking to strengthen your finance leadership team, get in touch with Rob Baker at rob@thecfopractice.co.uk.