Caitlyn Lewis: “Be specific about which areas your advisors can help you with”

Be specific about which areas your advisors can help you with. As women, we are so attuned to listening to others and taking on their opinions. And for the most part, this serves us well. But I have had to learn the hard way to be selective about who I turn to and for what […]

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Be specific about which areas your advisors can help you with. As women, we are so attuned to listening to others and taking on their opinions. And for the most part, this serves us well. But I have had to learn the hard way to be selective about who I turn to and for what specific advice. In our very early days at Supplier Day I made the decision to hire someone based on the recommendation of someone I trust a lot, despite having a lot of red flags. Needless to say, it didn’t work out. Would I go to this advisor for hiring decisions in the future? Nope. But would I go to him to ask for advice on how to sell to enterprise clients or how to raise funding? Absolutely!


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Caitlyn Lewis.

Caitlyn Lewis is the founder and Managing Director of Supplier Day, which creates net-positive virtual events for companies to engage with their suppliers. Throughout Caitlyn’s career in both start-ups and large corporations she’s learnt that how you communicate determines whether or not you achieve your goals. Now she’s on a mission to help organizations achieve their biggest sustainability goals by building stronger relationships within their supply chain.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I grew up in South Africa and then moved to London when I was 25. I had always worked in early stage start-ups because I loved being able to see the work I was doing having a direct impact on the overall direction and success of a company. I would generally be the first sales person the start-up was hiring to figure out how to sell their product at scale. Then I was contacted by Unilever in 2017 to join their Innovation and Transformation team. I was looking for corporate experience and wanted a big brand on my CV. The role was very open-ended as they were looking for someone who had start-up experience, who would help to shift their culture and mindset, as opposed to someone who had specific skills and could fulfill certain activities. It felt like the best possible scenario for me: for someone who loved working in start-ups for the lack of structure, I didn’t want to join a corporate company where I felt like a cog in the wheel who just needed to tick things off a checklist everyday to do her job. Whilst at Unilever, I helped them to overhaul their 25 year old innovation process and while doing this what struck me most, was how dependent the company was on their suppliers to do anything. At this time I was also completing my MBA through Warwick Business School. So I decided to focus my research on how large corporations are building relationships and dependencies with external partners to form business ecosystems. I looked at Novartis, Unilever and Vodafone. I loved the vision I was creating around how businesses could thrive when they built strong relationships and focused on delivering value for all stakeholders. But I kept thinking that if I was a CEO and read about business ecosystems I’d be thinking “this makes total business sense, this sets a great scene for the future of enterprise… but how do I do this?” And out of that, came the idea for Supplier Day.

Can you share the most interesting story that happened to you since you began leading your company?

I don’t think there’s any single most interesting story but rather, it’s the arc of my development and confidence as I built Supplier Day from concept to tangible product with provable ROI. When I started out I was really unsure of myself. I leant on my investors a lot for advice and guidance. But I started to build relationships with other trusty advisors — including our first customers — and that helped me to shape out Supplier Day. At the beginning everything is pretty muddled as you’re taking steps in the dark: it’s easy for imposter syndrome to take hold of you and at times, I would find it paralysing. But every little step I took led me into the light, so to speak, and now, 10 months in, I know who we are, what we stand for and the value we bring. And off the back of that, I’ve carved out the role I need to take as founder and managing director, and build my team around that to give us the best possible chance of success. So, ultimately, it’s the journey that’s most interesting. And what I love about that is that it implies that there will always be movement. I’ve got a great foundation now and I’m looking forward to growing Supplier Day and alongside that, seeing how my role as a leader evolves.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

You know, this gets me into trouble all the time but I often speak quite off-the-cuff. So I’ll say something in passing that, in my mind, obviously requires a lot more thought but the person I said it to takes what I said at face value. At the beginning, I needed to get my first customers on board who would serve as my “proof of concept” so I developed the pilot programme. Basically, we offered our product at cost price if the customer would allow us to use their name in a case study we could share with prospects. (I should add now that I ended up only ever doing this once because I realised it was unnecessary). But, in conversation with a well-known brand, I mentioned the programme and, in my off-the-cuff way, I added “there might even be an argument for doing this for you for free”. What I didn’t say was “we’d need to explore how to make this feasible and ensure there was longer-term value to be gained for Supplier Day” because I thought that was implicit. Needless to say I was shocked to receive an email a month or two later from the brand taking me up on my offer to deliver our product for free. And I had to go back and explain that I couldn’t just agree to doing something for free without understanding what the possible long-term payoff would be for our company.

At the time, I felt so incredibly stupid for saying what I did and I was worried I’d lose a potential customer at a time when we needed every brand we could get. But it taught me two important lessons: 1) You have to stand up for yourself. And if you can do it in a way where you can explain your stance and show you want to be fair to both parties, you will seldom lose the relationship. 2) Take a moment before you say certain things out loud!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There have been so many people who have got me to where I am today from my family to previous bosses, to my best friend and wonderfully supportive partner. But without a doubt, I would not be here without one of my investors, Mark Perera. He was the one who introduced me to the idea of ecosystems and connected me with leaders in Novartis, Unilever and Vodafone to do my research. He gave me the time and space I needed to develop. He gave me the idea for Supplier Day and involved Alex Martinez, my other investor, who has also been a major source of my development. It goes without saying that without Mark Perera, Supplier Day wouldn’t exist.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Hmmm… where do I start? I think, overall, it’s just not the expectation or the norm? We’re expected to want to get married and have families. So we’re treated as anomalies when we want to build businesses. And that’s why there’s this incredibly annoying discourse of being a “boss babe” or “she-preneur” or whatever other term you can think of. Why can’t we just be “founders” or “leaders”?

Alongside this, I think that founding companies is hard. It is just a hard thing to do and it’s going to be that way whether you’re a male or a female. But there’s an unwillingness to see, understand or accept that women face greater barriers to entry than men do, and then to implement things to change that. Things like access to mentors, funding and, even, support or belief in their potential.

It’s a bit of a funny tightrope to walk: on the one hand, we need to stop singling out the “woman-ness” of female founders as though it’s what makes us special. And then on the other hand, we need to be able to understand why it is harder to be a female founder, and work to change the systems in place that make it this way.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

I’ve found this question so hard to answer because it is never ending. And I mentioned a few things in my previous answer like access to mentors and funding. But I thought I’d answer this question by telling a story about my upbringing:

I grew up in a nuclear family: my mom, my dad and my older brother. And a common theme in my family was that personality-wise, I was more like my dad and my brother was more like my mom. My dad was a businessman and entrepreneur and, I think, because I grew up being told I had a lot of his characteristics and behavioural traits, the idea that I would also be good at “business” was implicit. And in much the same way, because my brother was likened to my mom (being more creative, arty and “left-brained”) I didn’t see any of those characteristics being gendered either. I truly believe that because of this I never once considered my female-ness as a thing that would impact my ability to be a business leader.

That’s not to say that I haven’t experienced sexism or haven’t felt external constraints as I’ve pursued my career. I have always been extremely aware of how I am treated differently as a woman and this has impacted many of my choices and even how I behave in a business environment. But, being a woman has never made me question, inherently, my ability to start a business and lead people. Sadly, I don’t think this is the case for most women.

And this is why I feel discomfort when I see VC funds being set up with the specific aim of investing in female-founded businesses. Or female-only mentorship networks. By doing this we continue to “other” women. We continue to make space for them only where space has specifically been allowed. And the underlying message is “you are different, therefore you need your own space, and you can’t play in the mainstream”. What we need to be doing is challenging the biases that exist in established systems. So we should be asking questions like “how do we get existing VCs to invest in male and female-led businesses equally?” and “how do we ensure that mentor networks are safe spaces for women?”

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

You know, there’s a great book called “Why are so many incompetent men leaders?” by Tomas Chamorro-Premuzic. The title is, of course, tongue-in-cheek, but the premise for the book is that there are a lot of traits that are considered more “female”, like being empathetic and a good listener, that make them better leaders. And I think that there’s a lot in that.

But I’d take it a step further: as women we tend to care about the overall well-being of society and the people around us. We are commercially minded, yes, but we’re less motivated by money and we’re more likely to take our social responsibility seriously. We want our employees to be happy working in our businesses. We’re interested in finding ways to win across the board. And when you think that customers are now expecting companies to take a stance on social and environmental matters, female-led businesses will be the ones to succeed.

So I don’t just see female-led businesses as ones that are better posed to be successful because they are more likely to be giving consumers what they want, but because female-led businesses are the ones that are building systems to benefit all of their stakeholders: customers, employees, suppliers, the society and environment within which they operate and shareholders. Ultimately, they’re the ones proving that profit does not need to come at the cost of all else.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

I absolutely hate “hustle culture”. You do not need to be compromising your sleep, health and nutrition in order to start a business. We have to stop admiring busy-ness and working crazy hours: they are not a sign of how much you care, how committed you are or how successful you are going to be. In fact, I would say that the successful entrepreneurs are the ones who prioritise their health and well-being because they know that their lifestyle has to be sustainable. There’s no point in burning yourself out so you’re incapable of serving your business and your team.

We all need to learn the difference between productive work and busy work. Productive work is the kind of thing that adds value and it will compound over time. Busy work is the stuff you do to make yourself feel like you’re working hard but is probably quite mindless and in all likelihood, could be automated.

I’m not saying that entrepreneurs don’t work hard. Of course we do! We have sleepless nights. There will be phases where we’ll be working long hours. But it’s not the norm. And we don’t celebrate it like it’s the thing that’s going to make us and our businesses successful.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

This is a really interesting question! I want to answer it by saying yes, there are specific traits that increase the likelihood of being a successful founder. But every time I think of a trait that would make someone a successful founder, like curiosity, being accountable, perseverance and committing to high standards of performance, I think that those traits would also make someone a very good employee.

The difference, though, is where these traits are more respected and offer a higher level of satisfaction. And I think that you will find these traits more desirable and celebrated as a founder or working in an early stage startup. As someone who has these traits I found working in a large corporate insanely frustrating because I was blocked quite a lot of the time.

So is everyone cut out to be a founder? No. On top of needing the traits I mentioned above, you have to be prepared to take risks and operate amidst a lot of ambiguity. You have to be so committed to your vision, idea, product or service that you will pursue it relentlessly. Ultimately, you have to be prepared to make sacrifices and be incredibly resilient.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)

  1. Be specific about which areas your advisors can help you with. As women, we are so attuned to listening to others and taking on their opinions. And for the most part, this serves us well. But I have had to learn the hard way to be selective about who I turn to and for what specific advice. In our very early days at Supplier Day I made the decision to hire someone based on the recommendation of someone I trust a lot, despite having a lot of red flags. Needless to say, it didn’t work out. Would I go to this advisor for hiring decisions in the future? Nope. But would I go to him to ask for advice on how to sell to enterprise clients or how to raise funding? Absolutely!
  2. Unwavering faith in yourself. The above story also taught me a valuable lesson in listening to myself. In the early days, I allowed people to tell me what to do. But as I found my feet as a founder and built confidence in my instincts I started to trust my judgement. And this also helped me to get specific about my advisors, as I’ve mentioned in the first point.
  3. Celebrate your differences as a woman . The sooner we start to recognise that we have certain traits, as women, that will serve us really well as leaders, the better. I used to think that being empathetic and wanting to find solutions that made everyone happy were weaknesses. But now I think they’re the things that will make me successful: they mean that I am always leaning into the needs of my team and my customers. And that means that I have an extremely committed team that have joined me in my mission wholeheartedly. As well as happy customers that keep returning.
  4. Put yourself out there, but safeguard your vision. Being a founder requires an extraordinary amount of vulnerability. We pour our hearts into achieving our vision and regardless of what anyone says, business is personal. So, as much as having close relationships with mentors is important, and as much as getting feedback from customers is really beneficial early on, do so in a way that safeguards what you believe in. Select your timing well and communicate what you’re looking for clearly, to ensure you get what you need from those around you. Early on, I used to go to my investors with just about everything to get their input. But I wasn’t structured about the idea and I didn’t articulate what I wanted from them. So I used to feel extremely disheartened after our calls when they didn’t express the excitement I felt or they started telling me what to do — it made me feel like I wasn’t good enough. Now, I take the time to think through my idea in greater detail before sharing it and I’ve become very good at articulating what I am trying to achieve. When I am ready to share, I ask for feedback pertaining to specific elements of my plan as opposed to asking for general opinions. It reminds me of Sara Blakely, the founder of Spanx, who didn’t share her idea with anyone because she knew they wouldn’t see what she did. And she didn’t want any negativity or people telling her she couldn’t do it to get her down. I feel that.
  5. Have a sense of humour — this is an absolute essential. One of the values we have at Supplier Day is “we can be serious without taking ourselves too seriously” and it’s got me through life. I am insanely committed to embedding the habits that create high standards: punctuality, respecting others, taking pride in our work and delighting our customers. But that doesn’t mean that we can’t laugh at ourselves, laugh at our mistakes and enjoy the journey. Life is too short to take it or ourselves too seriously.

How have you used your success to make the world a better place?

I like to think I am doing so, yes. There are two things I’m proud of at Supplier Day:

  1. We donate 100 trees per speaker for every single event we host, on behalf of our customers. My plan is to have a Supplier Day forest with 1 million trees.
  2. I’ve built diversity into the very heart of Supplier Day: I don’t want a single member of our team to look and sound like one other so whether I’m bringing someone on full time or they’re a freelancer who is working with us for just one event, I actively seek people who come from a minority background.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

It sounds simple but I think that that’s where big movements gain their momentum: it would be to shift the way that businesses engage with one another. Around the world there is a call for much greater focus on the climate crisis and specifically, we’re looking to businesses to reduce their environmental impact. But what’s scary is that about 80% of their emissions come from their supply chain. In the past, businesses would just shift the responsibility over to their suppliers but they’re starting to realize they need to lean in and help. What it’s doing is that it’s changing our commonly accepted views on what business is and how business relationships work. It’s humbling to see how many organizations are now seeking to find mutually beneficial outcomes as the basis for working with suppliers as opposed to the transactional and adversarial buyer-supplier relationships of the past. When companies seek to work together on projects that are about achieving a much greater purpose (like building circular economies, reducing plastic or becoming net zero) their motivations are different and this changes the kinds of relationships they have. I think this is going to have a long lasting impact on what value means to businesses, beyond profitable growth, to create systems, products and environments that genuinely improve the lives and wellbeing of many. To me, that’s powerful.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

You know, it has to be Elon Musk. In a way, he’s a bit of an anti-leader isn’t he? As polarizing as he can be, I think he is someone who is playing an infinite game and it’s challenging our standard approaches to doing business. Like making all the Tesla patents public. Or accepting payment in blockchain. Given my answer to the previous question, this is something I find really admirable. But in addition to that, he doesn’t take no for an answer and I think that takes a lot of confidence and staying power. Not to mention the sheer scale of the work he does is mindblowing. So I’d love to talk with him just to get some insights into how he thinks.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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