What I’ve learned as Chief People Officer in a fast-growing startup

In this guest post, Kel Hartman discusses her experience as Chief People Officer at Flywire, an international payments startup, and Paytrix, the fintech seeking to simplify international payments by unlocking access to the world's best financial services players through one contract and one API.

Kel is an Executive C-Suite leader with 25 years’ experience leading people teams in companies around the world. She’s also an award winner, respected speaker, and someone who has helped create high-performing teams alongside supportive cultures.

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As a Chief People Officer (CPO), your job is far from straightforward. The success of a company depends on its culture, and much of the responsibility in building that culture lies with you.

In a fast-growing startup, the task is even more difficult. That’s certainly the experience I had as CPO at Flywire, an international payments startup that I worked for between 2018 and 2021. In that time, the company scaled from just 100 people to over 450 and went public. Managing the culture of a company like this is an exciting, empowering challenge for a CPO. But it’s not an easy ride, and you’ll have to work hard to deliver the change and results you need.

So while every startup is different - week four at Paytrix is only confirming that - let me share what I’ve learned along the way.

1. 💯 A performance culture starts from the top

Without a culture of performance, your company can’t hope to succeed. That might sound pretty self-evident – but you’d be surprised how many don’t appreciate what this involves.

To build this culture, you first need to define what good looks like. For me, that’s always been an easy answer: performance = behavior + attitude. How you treat people and approach a task is as important as what you achieve. Once you’ve defined success, achieving it requires a three-pronged strategy:

✅Targets – Everybody in the company should have clear targets and areas to improve. You can’t expect people to succeed without telling them how. 

✅Incentive – You also need to make it worth their while. That could involve clear routes to progression or performance-related bonuses and salary increases. 

✅Support – You also need to give people the tools and resources to succeed. That could involve training, coaching, mentoring, or development programs.

It’s only by bringing all three tactics together that you can really create a success-focused culture.

2. 🤝 Get the right team for the job

All companies need different skills and experience as they grow. But for scaleups, the speed of change makes managing talent and skills a unique challenge. This is certainly the experience I’ve had at both Flywire and Paytrix. 

As the company grows, you need to be open to the idea that the people that took you to the first stage may not be right to get you to the next. There will be some people who just aren’t in the right role or organization anymore. There are plenty of reasons for this - some prefer the early stages of a company and may choose to opt-out. That’s perfectly natural – success requires getting the right team and those people who truly want to be there. 

This often involves difficult conversations, which takes courage and vulnerability. Before we jump to the dreaded ‘r’-word, there are plenty of other tools in your arsenal here. Many people just need the right support to succeed. Others are just well overdue a role change or some new responsibilities. You need to start with empathy; take the time to understand why people are under-performing before deciding the response.

Great performance conversations are as much about helping people succeed as it is about setting high standards. And sure, you will sometimes have to say goodbye to people who aren’t right – but it’s always better to be honest, firm, empathetic, and clear in these situations. 

3. 💪 Resilience doesn’t come easy

Life in a scaleup is high-pressure and fast-paced. Success requires resilience – and that’s not an easy skill to teach. Building resilience in a company requires, in my view, two priorities: encouraging frank feedback and proactively avoiding burnout wherever possible.

Giving and taking constructive criticism is hugely important in a startup. It’s not easy – but it’s a skill that can be learned. My view on feedback is simple: clear is kind, unclear is unkind (Brené Brown mantra). Leaders need to be fair, constructive, and make it easy to understand how to improve. Training and mentoring can really help here. Don’t expect leaders to just know how to do it; they need training on what effective feedback looks like.

And when it comes to burnout, training can also help people leaders spot the warning signs. Are people withdrawing from team chats, turning their cameras off in calls, or generally just losing motivation? These situations require empathy - managers should try to understand why people are disengaged and find proactive solutions. 

Encouraging breaks and digital disconnect days also helps here – and you need to lead by example. If your execs work twelve hours a day and never take time off, your employees will think they have to do the same – and that’s not good for anybody.

4. 🪙 How to get buy-in from execs

Training, mentoring, and bonuses all cost money. Often, other execs struggle to see the value of this investment. But it’s down to the CPO to convince them otherwise. So, how do you do that?

The trick is to understand what makes your stakeholders tick and what they value. Is it being well-known? Getting the maximum amount of sales? Keeping as many employees as possible? Whatever that is, it helps to demonstrate how your people strategy will contribute to those goals and to have the numbers to back that up. That last part is really important – if you can’t demonstrate the ROI of what you’re suggesting, you can’t expect others to buy in.

It also helps to find people that your stakeholders respect and admire to help you make the case. Put your ego aside here – it doesn’t really matter who takes the credit as long as the right decisions are made. Whatever tools you can employ to get the team on-side will only help in the long run.

The people strategy is really driven by other leaders and people themselves. There’s no point driving something that nobody wants, so it’s important to create initiatives that add value. In my first month at Paytrix, I had one-to-one chats with almost everyone in the business in all our regions to truly listen to them, consider their feedback, and use this as the basis of the people strategy. 

5. 📈 Managing acquisitions

Acquisitions are common in the scaleup world, and Flywire was certainly no exception. For a CPO, it’s a great opportunity to help create a company that’s more than the sum of its parts. But it’s also a challenge, because you have to take two different cultures, approaches, and ways of working that may be radically different - and merge them into a cohesive whole.

Success here requires taking the time to get to know people and understand what works before deciding how to integrate. There’s no point rolling out a one-size-fits-all strategy across the company, regardless of geography and skills. The last thing you want is for your new people to feel like you’re just bulldozing over their experience. I always take the time to meet people, perhaps flying out to their offices, hosting roundtables, or just going on a walk together to help break the ice.

Elsewhere in the company, we also offered buddy programs and made sure the new team had access to a decent induction and integration scheme. We also invited members of the new team into Employee Resource Groups (ERGs ) and wellness and recognition committees.

It also helps to move people about the business. Mixing people between the acquired and established business will help reduce the sense of ‘them’ and ‘us’. Whatever opportunities you can find to integrate these two entities will make a huge difference to the success of your acquisition. 

The keys to startup success

Across my career, I’ve been lucky enough to work for a whole range of companies right around the world. And sure, the startup world comes with a unique set of challenges; it’s fast-moving, volatile, and high stakes. But the advice in this blog isn’t just for scaleups: the fundamentals of a good culture are the same across any company of any size.

However large your business is, and however fast you grow, building a winning culture really does start from the top. It’s not a CPO’s sole responsibility, it's a team effort and getting it right isn’t easy. But if there’s one thing I’ve learned over the years, it’s this: your people are your biggest asset. They are your business, so take care of them, listen to them, be transparent, provide challenging opportunities, and develop them.

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To hear more, check out this webinar recording featuring Kel and Learnerbly CEO Rajeeb Dey.

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