In the latest episode of “Fintech Focus,” host Joseph Kamyar sits down with Pippa Hammond, experienced COO and GC, currently with a U.K. fintech and payments unicorn. Pippa shares her journey from private practice lawyer to fintech leadership, offering candid insights into the challenges and opportunities of scaling high-growth fintechs. The conversation covers her transition into broader operational roles, the importance of building robust legal, compliance and HR infrastructure, and how to balance innovation with regulatory demands. Pippa and Joseph also discuss the evolving fundraising landscape, the cultural shifts that come with new investors and practical advice for professionals looking to make a similar leap into the fintech industry.
Episode Summary
“Cash, compliance and customers.” Welcome to the three risks that keep Pippa Hammond up at night. Pippa, general counsel and COO of a U.K. fintech unicorn, explains how this “powerful trio” is often connected and “so hard to win and so easy to lose.” Tune in to this conversation with host Joseph Kamyar for insights into high-growth fintechs, examining how to balance compliance with innovation and why the “move fast and break things” mentality needs refinement in regulated sectors.
Key Points
- Transferable Skills: Legal training provides highly valuable skills that can be crucial in a startup environment, including problem-solving, stakeholder communication, project management and prioritization – all essential for operational leadership roles.
- Funding Reality Check: The “growth at any cost” era is over, replaced by a “quality over quantity” mindset in the investment marketplace. Investors now demand demonstrable track records, clear paths to profitability and strong unit economics, forcing a necessary discipline focused on being a great business, not just a well-funded one.
- Be Curious: Considering a move to the fintech space? Pippa’s advice is to understand the company, both its product and processes. “Engage with people, break down the silos, spend time with the teams outside your obvious remits.”
Voiceover (00:01):
Welcome to Fintech Focus, Skadden’s podcast for fintech industry professionals. The global regulatory and legal updates you need start now.
Joe Kamyar (00:15):
Hello, and welcome to another episode of Fintech Focus with me, Joe Kamyar. And today, I’m very lucky to be joined by Pippa Hammond, General Counsel of UK FinTech and Payments Unicorn. Pippa, welcome to the podcast.
Pippa Hammond (00:27):
Thanks for having me, Joe.
Joe Kamyar (00:28):
Why don’t we start by working through some background on you and your career? So, you started out as an incentives lawyer and former colleague of mine, and then since then you’ve worked through a series of fintechs, both as general counsel and COO, covering everything from online mortgage brokering, property, investment platforms, and most recently entering into the world of payments. So I guess my first question to you is how have you managed that transition from private practice lawyer to general counsel, and then onto a much broader operational role of COO?
Pippa Hammond (00:57):
Sure. So we’re back a few years now, and transparently, quite a lot of people thought I was completely mad when I made the transition. As you know, I left behind a great law firm, big glass building in the city, all the facilities, and dived quite literally into a basement in Old Street where I took meetings from a shed. And they were the days before Zoom, so safe to say it was pretty different.
(01:19):
That said, there were a lot of things not there in terms of facility and infrastructure, but as soon as you adopt the view that that in itself is actually a fantastic opportunity to be hands-on and build the business, create the culture that you want, and you want to grow and invest in, for me, that became a totally different proposition. So yeah, in terms of experience, you’re right, I took on a wide variety of functions, not all of which I’d actually grappled with before.
(01:42):
|So aside from legal and compliance, I did have a little bit of experience across some accounting, employment law, but I also knew that that ability to solve problems was something that would carry me and a reason people run businesses all over the place, so the answers must be out there. Actually, one of the things I think as lawyers, and our training, grounds us with a huge variety of transferable skills.
(02:03):
So, if you look at what we actually get up to day-to-day in private practice, we’re communicating with different stakeholders, we’re developing new processes, we’re juggling, we’re prioritizing, project managing. That’s a huge array of highly transferable and highly valuable skills that can be applied in a business context. As I mentioned, problem solving as a newly qualified solicitor, a FTSE 100 GC is at the end of the phone, your heart jumps into your mouth. The answer isn’t, “I don’t know.”
(02:28):
It’s, “I need to communicate in a way that reassures you that I can solve your problem and that I will go away and find a way to do it.” So that, I think, gave me a great grounding with which to approach the broader role. I’m incredibly grateful for the foundation that I have with my training in law, but I do think that a broader overview of the skillset that lawyers have is a really great one to sort of promote, and has carried me forward in terms of my own personal and professional growth.
Joe Kamyar (02:56):
Yeah. And I guess one of the things you touched on there was managing the resources available to you. It’s probably fair to say you’ve worked a number of fintechs all at quite different stages and life cycles. And it’d be interesting to pick your brains on the growing pains associated with scaling a fintech at pace.
(03:13):
And probably one of the things I hear the most from clients and GCs in this space, particularly in a regulated sector, is ensuring that, A, there is the legal risk compliance and HR infrastructure there to begin with and that it works.
(03:25):
But also, actually ensuring that that infrastructure remains commensurate and proportionate to the business as it grows, as it launches new products, as it goes through cross-border expansion, all of that.
(03:36):
So I guess my first question is, is that a concern that you share? And to the extent you do share that, how do you see organizations best manage that without siphoning innovation and growth?
Pippa Hammond (03:46):
It’s a really good question. And I think you’ve picked up on a ton of difficult challenges there. Actually, if you take a very traditional typical view of the world, lawyers and entrepreneurs should not get on. As lawyers, we are trained as perfectionists in many ways. We like to make informed and well-researched decisions, and that’s something that’s completely at odds with the nature of startups. Risk appetites are necessarily high. There can’t be right answers all of the time, and if the good enough needs to be acceptable in a scale-up environment. Very different, as you know, to common practices that we’re taught in legal training.
(04:20):
So actually, those two systems don’t necessarily gel particularly easily at times. It can be really uncomfortable. Many lawyers see ambiguity as an area of risk, whereas for scale-up startups, entrepreneurs, ambiguity equates to opportunity. So that old adage of move fast and break things is quite a useful analogy to draw on when it comes to talking about the proportionate application of infrastructure to a scaling business. So of course, the pace of innovation, growth is something that excites us about the scale-up space. That’s why we’re here today.
(04:57):
But bluntly, I think move fast and break the law isn’t a great recipe for exit. So I think it’s really important that legal and management teams completely aligned on the roles of the functions that you’ve mentioned, legal compliance and that internal infrastructure. The way I like to characterize them is as enablement functions. They’re not direct drivers of growth, but they facilitate.
(05:18):
And so for me, it’s incredibly important that they aren’t overlooked in the first instance when you’re building a company and an infrastructure from which to scale, because you need to do it sustainably. Where I’ve seen it work well is where the management teams are aligned. We all know where we need to get to. Fundamentally, we’re aligned. And the role of the business infrastructure is to help the business scale safely, to navigate regulation, but in an agile way or where perhaps there isn’t necessarily regulation.
(05:46):
If it’s a new or innovative space, then to create the best possible position, the most defensible position, that as and when the regulation catches up, we’ve set ourselves up well to navigate that to be successful. So, businesses that I’ve seen do this really well are the ones that do engage early with that regulatory landscape, and looking ahead to what might apply, why it might not apply. And I think there’s certainly a perception that compliance will slow things down.
(06:12):
And I think that’s where your question has been rooted from. That perception, I understand it. I’ve seen both sides of this. I’m absolutely confident that retrospective application into product, into process is a potential real impediment. It can derail roadmaps like nothing else, and it’s far harder to remediate once at scale than it is to invest proactively and upfront in your people, your processes. Get it right, have the people on hand to make decisions quickly with clarity of vision when it comes to these things. I think it also shows a maturity and can be a really powerful differentiator when it comes to investment.
Joe Kamyar (06:44):
Yeah. And I guess to what extent do you see that play into cultural shifts within organizations?
Pippa Hammond (06:49):
Growing pains for sure, for sure. I think it’s often the case that these more structured ways of working don’t necessarily suit everybody, particularly when most businesses have been moving fast, it’s scrappy, it’s fun, it’s dynamic. So it does have a cultural impact, of course, as you are bringing more rigorous, potentially, or onerous processes to a business, no matter how well-intentioned. You are with wanting to enable, I think there is a reality to it as well.
(07:18):
To navigate that, where I’ve seen it work well, is where compliance is positioned not as compliance for the sake of compliance. The FCA Handbook does not inspire anybody, me included. And by training, perhaps we should be more invested. But I think that where it works well is where it’s placed fundamentally as an integral part of the mission of the company, and it’s integral to delivering protection or a better customer experience or outcomes for those customers.
(07:47):
That can be a really powerful selling point in terms of, “Why are we doing this? A, because we have to, but B, and more importantly, because it improves our outcomes.” So, where you can clearly articulate the way in which that function is enabling, driving the company towards that mission, I think that’s the way that you get the culture of buy-in, collaboration, and it makes that cultural shift a little bit easier.
(08:11):
I’ve seen it be uncomfortable, I’ve seen it be ambiguous, but fundamentally, I think the key is making it a very conscious decision. Knowing that perhaps you have to build things from scratch, perhaps you’ve got people in the team who’ve come from backgrounds where they haven’t worked in regulated environments. Seeing it as a collaborative piece for education, and all pointing in the same direction towards that mission goal, as I’ve said, I think is definitely a really effective way of introducing what has to be done and getting the buy-in that is key to that success.
Joe Kamyar (08:41):
So, stepping back slightly, if we look back in your time as GC and COO, what have been the three most prominent risks or themes keeping you up at night?
Pippa Hammond (08:52):
Easy. I’ve got three for you, and they are cash, compliance, and customers. Makes it sound incredibly simple, but in isolation, each of those things are inherently complex. I think the reason that they’re a powerful trio, is each of them connected, they are so hard to win and so easy to lose.
Joe Kamyar (09:09):
The trio you referred to, so how have you seen that Trio shift as a business matures or have risks within that trio become more prominent? And to what extent has that impacted your role?
Pippa Hammond (09:21):
So I think the risks themselves fundamentally don’t change. We could talk about customers. That’s probably the fastest changing one of the three, in that principles stay consistent, deliver fantastic customer experience, generate top line growth, but the playing field’s constantly evolving depending on your industry. Customers are finding new ways to transact, to self-serve, in particular with AI. So the product you’re developing needs to stay relevant, needs to stay ahead of competition.
(09:46):
Compliance, on the other hand, changes at a slower pace. So the challenge here, particularly in my current business, is how do we grapple with it on an internationally distributed scale? It’s a big challenge to have. In terms of my own role personally, as I’ve grown into these, I spent a lot of my time in earlier stage companies building the machine from the ground up, putting in place the policies, the processes, the people to serve those day-to-day operations and make them work, iterate and improve.
(10:14):
There was a point at which I was also running the payroll myself. I think some would say a dark day when you put the lawyer behind the numbers, but everybody seemed to walk away happy. And I think all of those really hands-on experiences have been incredibly valuable in terms of the learning opportunity that that’s given me.
(10:30):
As the businesses have matured, role-wise I’ve been able to get into some of the more strategic stuff once those processes have been implemented, and to be able to then focus on strategy more quickly and really make sure that we are directing ourselves as a business towards those big existential risks.
Joe Kamyar (10:51):
Got it. And I guess when we’re talking about scaling fintechs, the next question is, well, how do you fund it? And it’s probably fair to say when we look at equity fundraising, at least over the past few years, it’s been a bit up and down. And we certainly haven’t reached the highs of 2021 quite yet, but what’s your sense for the market, and to what extent are you seeing companies recalibrate expectations around fundraising, or in fact, how they go about fundraising to begin with?
Pippa Hammond (11:15):
There’s a ton to talk about here. I think we’re absolutely seeing or have seen the death of growth at any cost. That recalibration you mentioned is profound, and it’s a reset of expectations across the board from the heady days you and I first fundraised in. So certainly, those challenges, I think I see it reflected at exec level in the boardrooms where there’s hugely intensified scrutiny on unit economics. And that push for the clear path to profitability is now an expectation, if not a demand.
(11:50):
So, the decks and business plans, where we were once striving for market share at all costs and the valuations that used to support those, are definitely gone for now. Where I think it’s actually taking us is a quality over quantity mindset in the investment market. And demonstrable track record is now a non-negotiable before approaching the market. So the hope, charisma and good vibes won’t cut it. It’s a changed reality. And does that slow things down? Possibly. Various tangents, we could absolutely talk about the AI boom and could prove me entirely wrong on that.
(12:24):
So while there’s overall caution, there’s still money out there for the right businesses. And I actually feel pretty positive about the fintech sector in particular, because we’re continuing to attract significant capital because we’re solving immediate and high value problems for people. So, the market has been through ups and downs, but it feels to me like the capital being deployed now is smarter and tied to real business value. I think it’s forced a necessary discipline in our sector and a focus on being a great business rather than just a great funded business.
Joe Kamyar (12:56):
So, you touched on some of the fundraisings that we’ve done together, and they’ve involved VC investors and also financial institution investors. And I guess obviously the immediate impact is a nice cash injection, which is fantastic. What other broader impacts have you observed with new investors coming in, whether that’s cultural or otherwise, beyond just the kind of immediate cash effects?
Pippa Hammond (13:19):
Definitely brings a cultural shift. And businesses I’ve been on this journey with have moved from that hustle, scrappy, “We’re just trying to survive” mentality that I mentioned, to, “We now have a mandate to execute for serious investors.” It’s a professionalization, and there are a few things that come with that, including a really healthy sense of purpose, but also a sense of structure and accountability that needs to be implemented. You have to align with the more disciplined professional standards of your new capital, particularly when that’s institutional. So it requires organization, new operating models. A lot changes fundamentally.
(13:55):
It’s a change I’ve also seen reflected in the boardroom. I’ll never forget the standoff I witnessed between a longstanding VC investor and a new board member, where the comment was, “It’s not about the numbers, it’s how you feel.” Turns out, it actually was about the numbers. That said, you see those board evolutions and you see a great wealth of experience coming into the room, a network, the disciplined approach. And for me, those strategics coming in can bring a lot more than just the cash when they’re used in the right way. So, it’s a really exciting advancement and opportunity for the businesses that I’ve been with who’ve been able to bring that caliber of investment on board.
(14:32):
So I guess the other challenge that comes with that when you’re changing up your exec teams, and one that can be super difficult to navigate, is the transition from founder-led businesses to more scalable, multi-layered oversight. It’s difficult, and often the reason the company has reached the point of the successful raise in the first place is because of the founder-centric leadership. But those next stages do often involve a move from a more single person decision-making operation as expertise joins the business. So prior ways of working need to evolve and a structured approach to decision making needs to take over. And I think these are fundamental people challenges that do come with scale. They bring cultural shifts, but the most successful management teams for me are the ones that lean into those, stay ahead of them and lean into them.
Joe Kamyar (15:18):
So, my final question is more of a practical one. You’ve stepped into multiple fintechs, as we’ve discussed, both as GC and COO, and presumably in all cases have had to get on top of a ton of information and detail in an incredibly short space of time. So, what advice would you give to someone looking at making a similar move or career trajectory to yours?
Pippa Hammond (15:41):
In the first instance, do it. You’ll never learn more. Once you get there, a few recommendations I would have would be to be curious and to listen. Don’t assume your past solutions fit the current problems. In fact, they probably won’t. So seek to understand the company, the product, the processes, and how and why they operate. I would engage with people, break down the silos, spend time with the teams outside your obvious remits. There’ll be a greater source of context, and you can’t really understand the business without understanding its component parts. And often, you’ll find deep risks and huge growth opportunities in those environments and having those conversations.
(16:16):
And then finally, I was going to say prioritize ruthlessly. It comes up in a lot of startup handbooks and a lot of literature, and obviously it’s key in scale-ups. You’ll have heard it before. You certainly can’t fix everything at once, so it is a very key discipline, and you have to get comfortable with being uncomfortable. But actually, I changed my mind in reflecting on what I wanted to conclude on. And I think the most important thing for me, and the best possible recommendation I can make to anybody jumping into a new adventure as I have done, is to be authentic, to know your place and your value at the table.
(16:50):
The most successful teams I’ve worked with are the ones where people trust each other, they’re comfortable to question, they bring different perspectives, different expertise, be that from legal backgrounds, finance backgrounds, engineering, commercial. It’s a huge opportunity to collaborate. And I personally believe I’ve got to where I am today by being happy to say, “I don’t know. Tell me.”
(17:13):
And I think that self-awareness of how and where you work best, what you have to offer, being able to be authentic with that is something intangible, but it also provides the stability and concrete foundation in an otherwise slightly mad scale-up world where everything around you is changing faster than you can often keep up with. I think that grounding is my strongest recommendation that I could offer. And obviously, have your in house counsel on speed dial at all times, Joe.
Joe Kamyar (17:46):
Sound advice. Well, Pippa, thank you so much for joining us.
Pippa Hammond (17:49):
Thank you so much for having me.
Joe Kamyar (17:50):
And thanks to everyone for listening.
Voiceover (17:53):
Thank you for joining us on Fintech Focus. If you enjoyed this conversation, be sure to subscribe in your favorite podcast app so you don’t miss any future conversations. Additional information about Skadden can be found at skadden.com.
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