Felicity Brown: Building Exit-Ready Organisations Through People

Career progression rarely follows a straight line. For Felicity Brown, Chief People Officer at Flintfox – a global pricing software company – the experience has encompassed nearly two decades of professional evolution, including her recent success in preparing Flintfox for its strategic acquisition in late December 2024. Her story provides the fresh perspective of a CPO navigating the complex dynamics of organisational transformation within private equity environments.

Felicity's career began at KPMG, where she spent nearly 13 years developing foundational skills in a demanding professional environment. "If you can navigate your way successfully through big four accounting and law firms, you can probably navigate your way through most organisations," she reflects.

During her time at KPMG, Felicity said HR professionals developed expertise behind the scenes, supporting partners and client-facing teams. This experience, while demanding, instilled rigorous attention to detail and analytical thinking that would prove invaluable later. Additionally, the audit-led culture created exacting standards where precision was paramount. "You really felt like everything had to be perfect," Felicity explains, a discipline that would later inform her systematic approach to organisational transformation.

Personal and Professional Transformation

Felicity's transition to MYOB marked a pivotal moment in her career trajectory. Working with a general manager who recognised her potential, she received clear guidance about stepping into a more prominent role. He would regularly remind me, "You are supposed to have the voice, Felicity, you are the one at the table."

This shift required significant personal adaptation. Felicity candidly admits to experiencing genuine imposter syndrome during her first six months, with daily commutes home punctuated by self-reflection: "Can I do this? Can I actually deliver what is expected? Am I confident enough?"

The breakthrough came through embracing a fundamental mindset shift. Her general manager's philosophy, "progress over perfection," became the catalyst for moving beyond her KPMG training in precision-focused execution. It was a principle that would later prove crucial in her approach to organisational transformation.

Preparing for Exit

When CEO John Moss approached Felicity about joining Flintfox, the brief was refreshingly clear: help transform the organisation to make it an attractive proposition for an exit. "It's a blank sheet of paper," Moss told her. "I need you to come in and do whatever you think needs to happen in the people and culture space."

Flintfox presented the natural challenges of a founder-led organisation transitioning to professional management. Like many entrepreneurial companies, decision-making processes had developed around the founder's deep knowledge and passion for the business. The evolution required helping managers build confidence in their own expertise and judgement.

Felicity's approach was methodical and inclusive. Over three months, she met with every leader and nearly every team member, gathering insights that would inform her transformation strategy. "When it came to determining what was going well and what we needed to do differently, I had real insights from the team," she says.

Guiding Cultural Transformation

The cultural evolution required careful navigation, particularly with the founder transitioning to a board role throughout the process. Felicity's strategy focused on building management capability while respecting the founder's continued involvement. "We really had to help empower our managers, help them understand they could make decisions that we trusted them with. That they didn't always have to seek approval for everything."

It was at this time that her philosophy of "seek to understand before being understood" proved instrumental in driving change while building on existing strengths. Rather than immediately implementing new processes, she invested time in understanding current practices: "Why do we do it this way? Should we continue doing it this way? Is there a better approach?"

Managing Staff Concerns and Cultural Challenges

Felicity says preparing for exit while maintaining team morale required a delicate balance, with some employees harbouring legitimate concerns about redundancy based on previous experiences with business sales. Her response was to ensure transparency and clear communication about the company's strategic direction.

"We were always very clear on what our job was and what it wasn't," she explains. The leadership team consistently reinforced that the focus should remain on delivering value to customers and growing the business, rather than becoming distracted by speculation about future ownership."

The challenge was amplified by Flintfox's global footprint, with operations spanning 19 US states, Canada, Australia, New Zealand, and Europe. This geographic diversity required nuanced communication strategies adapted to different cultural preferences. "For the US, they need an upbeat approach... whereas in the UK, they prefer directness – just tell us how it really is."

Navigating Complex Operational Realities

One of Felicity's most significant operational challenges involved the complexity of multi-jurisdictional compliance. Managing employees across 19 US states with limited resources created substantial legal and administrative overhead. "The compliance and legal implications vary significantly in each state, so it was like operating in 19 different countries. That was particularly complex for a small, lean company that doesn't have the resources that large multinationals do."

Due Diligence and Success Metrics

When Enable Global Inc. emerged as the acquirer – following a relationship that the CEO had cultivated over several years – Felicity's preparation proved its worth. She describes success in terms of "a really clean due diligence process," where the team could confidently respond to complex questions and demonstrate the organisation's capabilities.

"When you're getting difficult questions during due diligence and you're able to answer them easily, find the information you need, and provide the responses they're looking for – that's incredibly rewarding," she reflects. "You're showcasing your business."

Lessons from the Experience

Given the opportunity to navigate another transformation and exit strategy within a PE environment, Felicity says she "absolutely would"… because while it comes with a lot of challenges, I like the clarity of knowing my job is to help grow an organisation to make an attractive proposition for exit.

And, she says there have been some significant learnings she will take with her, including the importance of finding an authentic leadership voice, the power of inclusive change management, and the necessity of balancing short-term pressures with long-term vision.

Perhaps most notably, she's realised that successful exit preparation extends beyond financial metrics – to encompass organisational capability, trust, and resilience that creates value for all stakeholders.

"I really do thrive on turning things around, on empowering and exciting everyone involved so that it's not the leadership team telling the story of how far the business has come; it's our people. It's so rewarding when it's your team telling such an amazing story of success.”