From courtrooms to boardrooms, Annelene Dippenaar’s career has been shaped by curiosity, courage and a commitment to creating meaningful impact. Having transitioned from practising law into business and financial services leadership, she has spent more than two decades helping businesses grow while remaining grounded in values of integrity, empathy and innovation.
Today, through her work in financial inclusion and the informal economy, she is helping unlock opportunities for entrepreneurs who have long been overlooked by traditional systems. Here, she reflects on career-defining moments, lessons in leadership, the realities facing small business owners, and why the future of South Africa’s economy may well be shaped by those building businesses closest to the ground.
GLAMOUR: You began your career in law before moving into business and financial services. What inspired that shift, and how has your legal background influenced your leadership approach?
Annelene Dippenaar: I trained and practised as an attorney, but I was always drawn to the point where law meets commerce. I saw early on that if you understand that intersection well, you have the ability to create opportunity and build something that lasts. When the law creates the runway and business provides the tools to take off, magic happens — and I love to facilitate that. Moving into the commercial side felt less like leaving law behind and more like applying it where it could change outcomes for the business.
My legal background still shapes how I lead. It taught me to ask the right questions before forming a view, to read the detail others skim past, and to be risk-aware without being risk-averse. It also instilled a deep respect for doing the right thing — in how decisions are made, how people are treated, and how commitments are honoured. I firmly believe a business built on solid foundations will outlive those that don’t value getting the fundamentals right.
GLAMOUR: Looking back on more than 20 years in the industry, what have been the defining moments that shaped your career?
Annelene Dippenaar: Three stand out, and what links them is that each one pushed me out of my comfort zone and forced me to learn new, transferable skills.
The first was lecturing part time at the University of the Western Cape while working full time as a lawyer. As an introvert teaching in my second language, I had to learn to speak in front of people and juggle competing priorities at once.
The second was moving from practising attorney to in-house legal counsel. That’s where I learned that if you are genuinely obsessed with the business you serve, you give far better advice. If you work hard, you will get opportunities. The role grew into an executive legal leadership position, which gave me a fantastic seat at the table.
The third was leaving a job I loved and that I could do with my eyes closed to learning about the broader parts of the business including operational efficiency, the customer journey, marketing, sales and product. There I learned to problem-solve deeply, the importance of balancing getting stuff done, perfection and that being a leader means being in the trenches with your team.
So if an opportunity comes along that will challenge you and pull you out of your comfort zone, seriously consider grabbing it. I love the saying “Magic truly happens when you step outside of your comfort zone”.
GLAMOUR: What does being a woman in charge mean to you today?
Annelene Dippenaar: Earlier in my career I always felt like I had to apologise, or explain myself — but when I observed my male colleagues, I saw them own the room and be themselves, unapologetically. These days I actually don’t think too much about being a woman who leads. I realised I am not defined by my gender, my age or my background. It is about bringing my whole self when I show up.
These days I lead as myself. I rely on my strengths: accountability, tenacity, hard work, inquisitiveness, an ability to simplify the complex, and empathy. When women lead authentically, we widen the definition of what leadership looks like for the women coming after us.
GLAMOUR: Much of your career has focused on helping entrepreneurs grow their businesses. What are the biggest challenges facing small business owners right now?
Annelene Dippenaar: Cash flow is the first and most unforgiving one. Small businesses live day to day — margins are thin, income is irregular, and a delayed payment or an unexpected cost can be the difference between trading tomorrow and closing.
Layered onto that is red tape. We simply don’t have a business-enabling environment for the small entrepreneur, and that has to change.
GLAMOUR: Over the past two years, you've focused on the informal market. What drew you to this space, and what has surprised you most about it?
Annelene Dippenaar: I’ve always wanted to work in organisations focused on financial inclusion, so what drew me to Shop2Shop was the real, daily difference it makes in the lives of its customers. This is financial inclusion happening on the ground, every day. The township and informal economy is estimated to be worth about R900-R1.1trillion, yet it has been largely excluded from the tools the formal economy takes for granted. After years of helping established businesses grow, I wanted to work where the impact of every solution is immediate and visible.
What has surprised me most is the sophisticated business skills of these entrepreneurs. A shop owner knows exactly when their community gets paid, what customers can afford, and in what quantities — right down to selling single units rather than a full pack, because that’s what a household paid weekly can manage.
GLAMOUR: Informal traders and township entrepreneurs are often overlooked in mainstream business conversations. Why is it important to understand and invest in this sector?
Annelene Dippenaar: Because this is where a huge share of South Africans actually shop, eat, top up and transact every single day. The informal sector employs millions, keeps money circulating within communities, and absorbs economic shocks that would break more rigid systems. Overlooking it means overlooking a significant part of the real economy.
There’s also a fairness dimension. These entrepreneurs aren’t failing to participate in the formal economy — the formal economy was never built with them in mind. When we design financial tools around how they actually trade, rather than expecting them to adapt to systems designed for someone else, the growth potential is extraordinary. Investing in this sector is not charity; it’s one of the smartest economic opportunities in the country.
GLAMOUR: What are some of the most valuable insights you've gained from working closely with Shop2Shop customers?
Annelene Dippenaar: That trust is the real currency of the informal economy. Traders extend credit to their customers based on relationships and social accountability, not contracts — and it works. Any solution we build has to earn that same trust: it must be simple, reliable and visibly in the merchant’s interest, or it won’t be adopted. People assume price is the main factor in a purchasing decision, but while these traders operate on razor-thin margins, quality and trust matter just as much.
GLAMOUR: How can payment innovation help unlock growth opportunities for small and informal businesses?
Annelene Dippenaar: Payments are the starting point, not the destination. The first win is practical: accepting digital payments safely, settling in real time, and keeping transaction costs low enough that fees don’t erode already-thin margins. In a sector where cash flow is daily, getting paid instantly matters enormously.
But the real growth unlock is what payments make visible: every transaction builds a track record — a financial identity — that opens the door to stock advances based on actual trading performance, rather than paperwork the merchant doesn’t have.
GLAMOUR: In your view, what is the biggest misconception people have about entrepreneurs operating in the informal economy?
Annelene Dippenaar: That ‘informal’ means ‘not business-minded’. It couldn’t be further from the truth. These entrepreneurs are tech-savvy, financially astute and remarkably disciplined — they manage inventory, credit, pricing and customer relationships with a precision that comes from having no margin for error.
The second misconception is that they intentionally operate outside the law. As in any sector, there are always some who do, but in my experience the vast majority want to build a good business — one that provides for their families and complies with the law. The problem is that the laws regulating them are often nonsensical and poorly suited to how they actually trade. It’s not an unwillingness to comply; it’s frequently an inability to.
GLAMOUR: What trends are you seeing among South African entrepreneurs that make you optimistic about the future?
Annelene Dippenaar: The pace of digital adoption in the informal sector is remarkable. Merchants who were cash-only two years ago are now accepting cards, selling value-added services and using transaction data to make decisions. Customers are driving it too — demand for digital payments in townships is growing, and entrepreneurs respond, because they always do.
There’s also a generational shift. Young people are entering informal trade as a deliberate business choice, not a fallback, and we’re seeing more and more of them building solutions and services for the sector itself. That changes everything about its trajectory.
GLAMOUR: Have you encountered any challenges as a woman in leadership, and what lessons have those experiences taught you?
Annelene Dippenaar: I spent much of my career in law, credit and fintech —I was often the only woman in the room, and where credibility had to be earned twice, through incredibly hard work. But, honestly, very often the challenge I felt was one I created myself, by assuming that being a woman in the workplace meant something it didn’t. We assume we can’t ask for the flexible hours that let us parent and work, because we fear it will create a perception that we can’t be counted on — all the while our colleagues ask for what they need without it ever crossing their minds. Yes, stereotypical thinking about gender still exists, but if we hold ourselves back because of it, we lose out. Very often, we are the ones overthinking it.
Those experiences taught me three things. Own who you are — don’t make yourself smaller. Preparation is power — when you know your subject cold, the room adjusts. And allies matter — find the people who amplify your voice when you’re not there.
GLAMOUR: What qualities do you believe are essential for women aspiring to leadership positions?
Annelene Dippenaar: Curiosity, first — the willingness to keep learning across disciplines. My own career has spanned law, data, credit and payments, and every leap was powered by being genuinely curious about how things work.
Second, resilience, tenacity and grit. Leadership involves setbacks, and the ability to absorb them without losing your sense of self is non-negotiable. You have to keep going, even when it’s hard.
Third, decisiveness paired with empathy. You must be able to make the hard calls, but how you make them — with fairness, and respect for the people affected — is what builds a team that will follow you anywhere.
GLAMOUR: What advice would you give to women who want to build successful careers while staying true to themselves?
Annelene Dippenaar: Early on, I thought success required adopting a style that wasn’t mine.
The turning point was realising that the very qualities I’d been tempted to mute were exactly what made me effective.
Practically: let substance be your signature, because deep competence is the most durable currency there is. Be inquisitive and curious — don’t assume the person already at the table is right. Ask for the role, the raise, the seat — when deserved, and without apology. Surround yourself with a tribe that gets you, grounds you and supports you. And seek out diversity: you learn more when you engage with people from different backgrounds. Above all, define success on your own terms — a career that costs you yourself, or steals your joy, is not a successful one, no matter what the title says.
GLAMOUR: How do you switch off and recharge outside of work?
Annelene Dippenaar: Time with my family and being outdoors are my reset buttons — living in the Cape Winelands makes that easy. I love long-distance running, usually with friends, and there’s nothing better for clearing my head. And I protect time to read; it keeps me curious, which I consider as much a professional asset as a personal pleasure.
GLAMOUR: If you could leave one legacy through your work, what would you want it to be?
Annelene Dippenaar: I’m going to be ambitious and go for two. The first: that businesses once invisible to the formal economy become impossible to ignore — that, because of the work we’ve done, a small business owner has a financial identity, access to credit on fair terms, and the tools to grow a business that supports her family and employs her neighbours. And alongside that, a quieter one: that I was a leader who supported and encouraged my team — that they grew, and went further than they ever thought they could.
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