What’s your story?
Like a lot of other people who were coming out of university graduation at the same time, I sort of fell into tech and ended up at a really early-stage startup. We were trying to reinvent the condo management industry. It was all things challenging, but it really was a role where customer success was wearing all of the hats. It was Support, it was Product Management, it was all of the things that connected with customers, or potential customers and products. So I think I was in a customer success role so far as the title, but I would say that it was a lot more of an operational and support role.
I moved over to a company that did Virtual Data rooms, which is like, the least sexy thing you could ever work on, but it was a really good place to get some experience in a customer success specific role. So we really had for the first time I had ever seen, good customer health scoring and the idea of proactive customer success, as opposed to a much more reactive function, which is what I was doing before. I actually moved to the UK to open up a UK office. So I got the opportunity to live in London, which was amazing.
I’m originally from Toronto, Canada and I’m currently living in Vancouver. So I guess that’s a little bit of a spoiler alert but I ended up on the West Coast. Partly because of the weather. I don’t ever want another Ontario winter. No offence to the Canadians, but you’re much braver than I am.
I essentially got really wrapped up in a company called Monzo. For anyone who doesn’t know what the pink card was, in the early days, they were offering I think it was like five pounds for every person that you referred, who signed up. Again, I was such a super fan. I think I made like 100 pounds, it was so good. Following that, I got really obsessed with FinTech. Especially, there was so much happening in London – the heart of FinTech and still is. I was actually approached by Pleo, which is a FinTech company based in Denmark, a company spending solutions. It’s the ability to give cards and empower your employees to spend without barriers of issuing a massive amount of company cards from your company bank account, which is an awful process, and then end to end it automates your expense report.
I ended up joining Pleo. I was there from A to Z. We raised our series seed just before I left and we had a unicorn status which was very exciting. But an amazing experience like super fast-growing, I guess a crazy market expansion as well as building a product alongside the growth in those different markets, so really exciting stuff. When I joined Pleo, they were only about 60 people and I was one of the first in the UK office. Now they have over 300, which is just crazy to think, but I lead the UK CS team, which was a great experience. Fast forward to now – late last year I actually made the leap, figuratively and literally, made the leap to Float.
Float is a company card solution, where we focused on Canadian businesses. So I made the leap to join Canadian business, made the move back to Canada and then further to that, we’re the first Canadian expense management product on the market, which is actually pretty cool if you think about how crowded the space was getting in the UK, even around the time that I left. So I joined Float as employee number eight. We’ve grown super quickly since we recently raised a $30 million Series A, and we’re hiring right now, so if anyone is looking for a new opportunity, reach out, we’d love to hear from you.
What are your lessons from building up a customer success team from scratch in the startup environment?
Oh my gosh, where do I start? A few of my biggest learnings from Pleo and especially growing the team is to hire Customer Success leaders early on. I’ve seen Customer Success Orgs, ourselves included, that fell into a little bit of a trap, where we tried to train too many people on how to be customer success managers. And that’s it. It’s amazing and surface selling but it is a huge amount of time and energy and resources that go into training people and making sure they understand what customer success is. Because while you’re growing a team, you’re also at the same time trying to figure out what customer success means to the organization, and how those areas feedback into the business as a whole. So I would say that was big learning – hiring senior CSMs, who understood the ups and downs and potential challenges of a customer success role.
The other one would be data. Invest in data early, and invest in all of it as much as you can. Leveraging data is so powerful, and is the only way that you can really scale up customer success and Customer Success activities. A lot of the time it kind of feels, if you don’t have data to back something up, it feels like you’re guessing. And even with data, at Float, we have lots of data and it still sometimes feels like we’re guessing, we’re testing out things and scrapping them and moving on to something else. So I would say so long as you have the data, you can actually be experimental. But if you don’t have it, it makes it really difficult to do any of those tests or make any of those samples.
Those are really great lessons for building a team within the startup. I could agree wholeheartedly – hire great people, you really need someone ready to hit the ground running as soon as they start. You don’t have that much time to train them on the whole customer success. You can rely on them. And then you have time to figure out what customer success is in the company. So thanks for sharing that. Another thing that I noticed about you and your career move is that now for a few times you moved within the same space within FinTech. You could have gone to any other company or startup in the world, but you chose to stay within the same industry. So tell me, what are those advantages of being an expert within the industry?
It’s something that I think I undervalued early in my career and only as I got later in my journey, have I realized the importance of it or at least the power of industry knowledge and the idea. I think that has been a massive advantage, it’s meant that I was able to ramp up in a shorter period of time. But then second to that, it was also much quicker for me to gain the respect, to actually make decisions or suggestions for the companies that we were bringing on board. So I think being a really trusted expert in the space cannot be undersold. A big part of customer success is really advocating for customers, and then also challenging them on their processes. I think that’s really difficult to do if you don’t understand the entirety of their business and how their business functions and how they’re going to be interacting with your product. I think that has been a massive advantage. It’s something I actually wish I would have explored earlier on in my career because it has really carved out this career path, which I mean I couldn’t have even guessed five years ago. But now that I’m in it, I can’t imagine being in another industry.
You can hear the passion from your voice about FinTech about customer success!
I love talking, I love talking about the eradication of the expenses like they’re all on fire.
Natalie, another thing that I picked up from your story, which is really interesting, you were building a startup from the ground up. So you’ve been one of the early employees at Pleo, building the CS team from the ground up, becoming a team lead and getting into leadership role. And then as you moved to Float, you are back in the individual contributor role, but you are also building the team and hiring. What are those challenges like, firstly, when you move from the leadership back to individual contributor, and then just trying to build a team and be there for your customers?
It’s such an interesting transition. It’s something that I thought a lot about before I joined Float. Now that I’m at Float, I realized that the parallels and the similarities between managing a team and managing a book of business are so similar. And the pieces of the individual contributor that are the most interesting to me is the amount of time you actually get with customers. So especially when you’re new to a business, coming into a management role can sometimes be really intimidating. You are usually managing a team that knows a lot more about the product than you do. So I think the move to individual contributor, perhaps being in such a small team, it’s not as noticeable, but when you go from a bigger organization or even leading a bigger team back into IC, it can be a big transition to suddenly talk to businesses all day whereas you were probably just communicating through your team before.
Is it true that you joined Float as the first woman on board?
Yeah, I was the first female employee on board, and it took us a while to hire more women. So I think there’s a question there. And it’s something we think about a lot, we’re pretty self-aware, I would say at the very least. I was the first woman on board and we had a lot of discussions about how you actually look at representation and how much representation really matters. For me, I had a bit of a soft landing, I knew the person who was joining as a CEO of Float. So that made me feel more comfortable but if I was an outsider, and if I was a woman looking in and looking at some of the roles that we had posted, and then looking at the employees that Float had, I mean, it’s entirely men, that’s pretty intimidating. So we’ve worked really hard to try to bring up the visibility of our leadership team and what life looks like at Float but it’s something we think about pretty constantly. It’s definitely not something we have fully mastered. We’ve hired and brought on some more women, which is amazing, we have enough women to have a private Slack channel, which I think is a really good sign.
Oh, that’s a really good thing! Channels are my thing and knowing that you have an all-women group already is cool. As you’re hiring, what have been some challenges that you have seen in that attempt to bring more women on board to really make a much more diverse team? What are your observations?
Yeah, I think it’s such a tough one. There are two pieces to this because I think it’s also super relevant when it comes to mentors, mentees, and the people who you’re looking to learn from in the company. I would say that one of the things that we really struggle with, or I’ve personally struggled with and hiring into Fintech is that there are not as many women in senior positions. Both in FinTech and I was previously in legal tech, both are really male-dominated fields. So it’s been really difficult to even connect and network with women who are in more senior and executive positions because there are just fewer of them. I think that makes it really competitive and really tough to hire women in some of these smaller startups, especially where the name isn’t, as well known.
What was your experience in mentoring so far in your career that you would like to extend to other women who would like to enter the industry?
Oh, mentor, mentorship, and mentees, get all of them and leave every opportunity that you have to bring on either a mentee or on the other side to get a mentor. They can be such powerful assets when it comes to personal and professional growth. Especially I found when I’ve moved into a management role, having those mentor relationships has made a really big difference in terms of sometimes the senior management exactly, as I mentioned, is, for the most part, male-dominated. And if you can find a mentor that has a similar level of seniority, I think having that perspective is so valuable. I have learned so much even about things like potential pitfalls, or learning from other people’s experiences, which is partially why everyone listens to this podcast, right? It’s like which snippets can I grab from someone else and maybe not make the same mistakes or maybe follow a similar course of action?
It sounds like you are finding mentors all around you, learning from people wherever you can, wherever you have the opportunity. What would be your advice for women who are looking to find a mentor?
Yeah, I mean, there are so many amazing online communities. Now I’m interviewing for the customer success role I always ask, what are you doing to learn more about the industry because there are so many resources for customer success out there. It’s limitless in the number of people that you can connect with. There are some amazing women in the space especially like the CS with Emily, which is Emily Garza. Fantastic content, she’s amazing. And for me, it was such a blessing to find, because that spoke to the way that I run my CS teams, that’s the way that I think about customer success. And she kind of shared some of the learnings that she had, especially moving into a management position. So even reading content like that is super powerful. So I would say start there. I think that the crux of it is that anywhere and anyone can be a connection, it’s really just how you utilize those.
As we are approaching the end of this conversation. Firstly, thank you for sharing all those insights. There are so many lessons that someone can take for their career, from your experience. What would you say was one of the best career lessons that you have learned so far?
Yeah, I think the best career lesson, gosh, that’s a hard one. There has been so many. I think one is don’t run before you can walk. Building a foundation is one of the most, I guess, like, a foundation is everything. You can’t build a house without a rock-solid foundation. So don’t rush the foundation, really put effort into the early stages. One of the best people I’ve ever worked with Soren, he was the other half of the Pleo leadership team. But his favourite quote, it’s an Airbnb quote (we’ve totally stolen it) but it’s “do everything by hand until it gets painful.” And that’s how I feel about the early days of building the foundation is that you’re doing it by hand. It’s going to be super painful, but I promise it will be worth it. So don’t skip those steps to move forward to putting you know, they’re like the star on the top of the roof.
Natalie, this has been such a wonderful conversation. Thank you for coming to the show.
Thank you so much for having me. It’s been so nice. And now I get to be a first-time guest but a longtime listener finally.