Navigating success: stories of triumph and resilience, Part 2

“...It is an incredible feeling to realize that the future is constrained only by our execution against the goals we set for ourselves. Nothing is holding us back from building the company we’ve dreamed of...” - Jessica Long

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Welcome to the second part of our 3-part series tagged “Navigating Success: Stories of Triumph and Resilience”. The series is dedicated to exploring the inspiring journeys of three women entrepreneurs in celebration of Women’s Month, highlighting their achievements, and the resilience they demonstrated in overcoming obstacles. We'll also explore their unique approaches to building diverse and inclusive teams, fostering an environment where all voices are valued.

This week, we meet Jessica Long, the President and Co-founder of Maad, a tech company modernising informal retail in Francophone West Africa. She can most likely be found precariously balancing her computer on top of some sacks of rice, playing with her god-daughter in one of Dakar's many rooftop pools, or aspirationally trying to start another book club in Dakar.

Damilola: Jessica, it's fantastic to have you on board for the series!  The tech startup scene is still young but maturing, and it's awesome to chat with someone right in the thick of it all. Let’s rewind a bit. How did your journey into the whole tech startup scene start?

Jessica: I’ve been interested in programming since I was a little girl. I didn’t always recognise that what I was doing was programming: to me, I was “making games” or “writing instructions to describe how a story should be displayed.” But all of this was ultimately teaching me how to code.

I got an undergraduate degree in Symbolic Systems and a graduate degree in Computer Science from Stanford University. When I graduated, I was eager to apply my skills to a place that could benefit from what I had learned in college. While most of my college friends took entry-level jobs at Silicon Valley tech giants and start-ups, I moved to Burundi to work as an IT manager at a rural hospital. I was eager to see how tech could be applied to providing better, more reliable services for underserved communities.

After a couple of years, I moved back to San Francisco and took my first tech start-up job: as an early software engineer at Airbnb. I watched as Airbnb became a global phenomenon – one that I helped to build. It was vertiginous, to watch how Airbnb started to shift commonly accepted ideas of how people travel. And to feel that, even as a 25-year-old on a 15-person software team: I was a meaningful part of that.

Yet even as an individual contributor at a tech start-up, I never thought about founding my own company. It didn’t seem necessary: I thought there was a lot to accomplish with already-established companies. I took another job in Senegal to continue my earlier work designing digital tools for rural health centres across West Africa.

It was finally in Senegal that I started to think about building my own company because when I looked around, I saw opportunities everywhere unlike in Silicon Valley.

I was very lucky to cross paths with Karimou Ba; a brilliant entrepreneur who had already founded two companies by the time we started working together. He brought in our third equally brilliant cofounder, Sidy Niang. I know for sure that we couldn’t have built Maad without all three of us: three friends who believed in the potential of data to transform the way business is done in Senegal. And then specifically, to fundamentally transform the logistical and financial landscape for distributing the products that people consume every day in West Africa.

I never could have imagined starting a company while I was living and working in Silicon Valley. But 4 years into my journey with Maad, I can say for sure: This is the best and most meaningful work I’ve done in my life.

Damilola: Your experience in Senegal must have further opened your eyes to the potential of tech for underserved communities. But let's talk about starting your own company. When you were starting, did you know just how big of a deal the problem you're solving would be? Or was there a point where you realised the real impact you could have? 

Jessica: One moment that stands out to me is at the start of our delivery journey. We had decided to start providing distribution services to boutiques, but we ultimately weren’t sure if they would buy from us. Surely they had their existing suppliers. We weren’t sure what added value we could provide, at the very beginning.

In the first three days, we sold $1,000 worth of products. It was a huge sum to us at the time. For reasons we didn’t yet understand, the shops were responding very strongly to our product offering. We started getting requests every day from people demanding help in getting our app set up. I had never before experienced this level of demonstrated interest in a service I was piloting.

We hadn’t even launched the value-added services that we planned to complement this offering with (digital credit, insurance, and inventory management tools). And already, the simplicity, reliability, and transparency of our services was a game-changer.

As I triangulated this level of demand in my head with the sheer number of informal retailers offering similar services, I started to realise that we’d finally found our “white whale” – a goal that could absorb all the passion and energy and technology and funding that we could pour into it.

Damilola: Absolutely fascinating, Jessica! That initial surge of customer demand must have been incredibly validating. Speaking of milestones, can you share a defining moment/achievement in your entrepreneurial journey that you are particularly proud of, and what factors do you attribute to the achievement?

Jessica: There are a lot of things that I can cite here, but I’ll mention two as particularly satisfying.

The first is the warehouse that we built from the ground up. Every day I come to this space, and I see what we built from nothing. In the beginning, my cofounder’s brother had lent us a tiny 20m² garage space, where we stored about 20 kinds of beverage products. We had a team of two or three, and we often ended up in the tricycles ourselves, making our own deliveries.

Today, we have a 2,000m² distribution centre (soon to be 4,000m²). We’ve designed the space ourselves and learned how to manage a space, a fleet of trucks, and a highly available web platform. There are more than 100,000 individual units of products sitting in the warehouse that turn over every 4-5 days. It’s kind of awe-inspiring to come out onto the balcony that I designed, and peer over into a loading area filled with 100 busy employees.

The second is related to tech. There have been many moments along this journey where I feared I couldn’t do something because I had never done it before. One time when our site was getting slow at peak times, I was worried that I was not a DevOps engineer. But when I rolled up my sleeves and started inspecting the code, we handled the blocking points one by one. Today, I think of myself as a full-stack, DevOps, Android developer – and more.

I think what enabled both of these accomplishments was the willingness to face new challenges head-on. To be honest with myself about what “the most important” problem was and even if I didn’t feel like it was something in my wheelhouse, to have the confidence to know that I could learn to do things I’ve never done before. And to systematically take up each new challenge one by one.

It’s by facing, and solving, 1,000 little issues (while always keeping the big picture, and the mission, front and centre in your mind) that you ultimately build a thriving company and a solid base to work from.

Damilola: Building a company from a tiny garage to a large warehouse is undoubtedly a testament to constant learning and growth. It sounds like there must have been some bumps along the road. What strategies did you employ to maintain resilience during tough times in your business?

Jessica: Being an entrepreneur certainly comes with its share of tough moments. The responsibility to always find a way forward, to fulfill ongoing obligations to investors, employees, and clients, inevitably comes with a lot of pressure.

In our toughest moments, I’ve always leaned on my cofounders. I know for sure that we couldn’t have created this company without each other. When one person gets tired, the other two pull them back up. I also find motivation in my collaboration with them. In the early days, when the company was mostly just three friends coding in a family garage, I took inspiration from how hard my co-founders worked. I wanted to match them in talent and drive.

When I get scared, I try to stay very concrete about our goals. It’s easy to get caught up in a high-level feeling of dread. But many times, you just need to sit down and ask yourself: “What’s the next step?”. “How can I make a little progress today?”. Also, I try to always find little accomplishments to count as wins.

Damilola: Jessica, thanks for such a sincere response and a powerful reminder of the importance of a strong team. But even the person with the most supportive network experiences moments of doubt. What motivates you to keep pushing forward and pursuing your goals in those uncertain times?

Jessica: I always come back to focusing on the mission - what the startup represents to me and what it means for others.

2022 and 2023 presented a difficult financial climate, where we were forced to adapt as a startup to stay alive and thrive. We had to make tough choices, like closing down two of our warehouses to consolidate into a single facility and accelerate the path towards profitability. Fundraising was slow-going; I felt like I believed so much in the story I was pitching, and yet I couldn’t get others to believe it, too. It definitely felt like I was letting down the rest of the organisation.

What helped me stay motivated and focused was reminding myself constantly of why what we are doing is hard and why it has value. We are building a tech-first, operational company – to create new kinds of job opportunities in a country with high unemployment rates and low literacy. We are making significant investments in physical and digital assets – to unlock opportunities for fintech and other value-added services that can’t function without the base layer, tech-enabled infrastructure in place.

Every time I got frustrated with how things work or scared that we wouldn’t be able to bring our vision to life – I reminded myself that the reason these things don’t exist yet in Senegal is precisely because of these challenges. It helps me stay patient, focused, and strong.

Damilola: That’s inspiring. It sounds like your 'why' is crystal clear, and that it helps you manage doubt. What I also see/hear from your responses so far is a demanding schedule. How do you prioritise self-care and mental well-being while managing the demands of entrepreneurship?

Jessica: To maintain balance, I tend to set aside periods where I can focus nearly 100% on the business, followed by periods where I can rest and recharge. I’m kind of an all-or-nothing person, so I like having these periods of deep focus, alternating with periods of rest.

For me, this looks like designating months as an “on” month, where I will push every day at 110%, or an “off” month, where I will continue to meet the everyday needs of the business, but will give myself the grace to sign off at dinner time or take time for an extended weekend with friends. This is possible because of a strong team with overlapping skill sets; we trade off the role of being “on-point” for the inevitable challenges that come up in such a sector that’s as operationally focused as distribution is (and as technologically demanding as we are making it).

The other strategy I have is to take advantage of the freedom I have through entrepreneurship. This freedom has advantages and downsides; on the downside, I’m the ultimate backstop at the company so if there’s a major issue, I am responsible for always making sure that we find a way forward. But the plus side is if there’s a morning with no meetings scheduled, where it’s business as usual, I also have the freedom to have a lingering breakfast with friends, with no consequences to the business.

I think it’s important to balance the demands of entrepreneurship with a similar level of “demand” for your personal life so that it gets treated with the same attention and care. 

Damilola: Alternating intense focus with dedicated rest periods sounds like an effective strategy. Among the readers of this interview would be women, possibly aspiring female entrepreneurs. What key lessons or insights would you share with them or your younger self?

Jessica: I’d share one key lesson. Being an entrepreneur involves learning to become comfortable with failure and rejection. I think this is hard for high-achievers, by default. And it’s especially hard for women.

In the working world, you are often evaluated on whether your performance is “excellent”. And the default answer is assumed to be yes. The goal is to become a little more excellent, but usually, you’re already doing a good job, at a baseline.

As an entrepreneur, you start with nothing at all. You’re not doing a good job by default. In the beginning, you’re not producing anything at all with demonstrable value! Everything’s a dream, a vision, a prototype, an “ask” for a favour.  You go through 100 nascent ideas where you go above and beyond for a potential client, and yet overall, the lead doesn’t pan out. You keep feeling like 1+1=0, over and over again.

But one day, you hopefully get to experience that treasured, elusive moment. A “click”, where suddenly things feel so much easier than they did before. Usually, it’s the first sign of “product-market” fit. You feel like what you’re doing makes sense. The feeling is that 1+1=3. 

To me, this moment is everything. It’s why we do entrepreneurship: to unlock these heady, incredible moments where things fall into place and you get to experience exponential growth. 

I think my younger self (and many women) would have been uncomfortable with how many times I had to continue to pick myself up after another disappointment. But that’s the whole game! And if you do end up finding the “point de départ”, the feeling of ease and expansion that comes alongside that — especially after the months or years of struggle that preceded it — is a feeling like no other.

Damilola: 1 + 1 = 0 to 1 + 1 = 3 is an interesting analogy; the struggle is real, but the payoff sounds incredible. As we wrap up, can you share how you approach building a diverse and inclusive team, and why is it important to you?

Jessica: Building a diverse and inclusive team is extremely important to me as a founder. It’s one of the most meaningful things we’re doing at Maad.

There’s so much to say on this topic, but I’ll highlight a few discrete points. First,  we had a very strong starting point by starting with an unusually diverse and complementary group of co-founders. I think this is often not the case; people often choose to work with people who are very similar to themselves. This makes it harder to attract a diverse talent pool later on, because you’re all starting from the same base network. However, with Maad’s co-founding team, there is real diversity in age (there’s a 5-year age gap between me and each cofounder), nationality (I am an American working with two Senegalese nationals), gender (2 men and 1 woman), expertise (tech + finance + entrepreneurship), and working style (an inventor, an optimiser, and a hustler).

When you start from this broad basis, it’s easier to attract diverse job candidates, who will have an easier time seeing themselves in one of the distinct founder profiles that already exist on the team. This helps to find genuine complementarity and synchronicity in the team.

Secondly, we’ve always been attentive to being inclusive to women. Our senior management team is 50% women, and our sales and call centre teams are both largely female. We’ve made this effort in part because we know that tech and logistics are heavily skewed towards male participation.

Lastly, we make an effort to recognize the specific needs that women on our team have, logistically and interpersonally. We’ve helped a star field sales agent transition into a new management role during her pregnancy, that was less physically demanding for her. When we noticed that women were less likely than men to speak up in group meetings, we switched our meeting style to include more 1:1s, where our female teammates are more likely to share what’s on their minds. 

We try as much as possible to make our objectives and evaluations KPI-based, to avoid any unconscious bias that comes with evaluating others’ work in the absence of clear targets.

Thank you, Jessica! It has been a pleasure learning about your journey.

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