Where legacy meets vision: How Anna Weylandt is redefining strategic growth with the Enneagram

Anna Weylandt | Director of Strategic Growth and Brand Development
Enneagram Core 7 

There’s a quiet power in doing things your own way, especially when it’s backed by legacy, vision, and bold creative fire. That’s the energy Anna Weylandt brings to her role as Director of Strategic Growth and Brand Development at Weylandts, one of South Africa’s most iconic lifestyle brands.

Her journey began in the world of hospitality interior design, where she cut her teeth under the guidance of a creative director who taught her the art of hard work and the magic of loving what you do. At 24, she was invited into the family business as the first official furniture buyer. At the time, this department didn’t exist, with her father and CEO, Chris Weylandt, still doing the buying himself. She was brought in not as a figurehead, but as a builder. A visionary. A change-maker. She stepped into an undefined role and turned it into a powerhouse product design department, now responsible for conceptualising and sourcing over 200 unique furniture pieces each year.

But she didn’t stop there.

Five years ago, she took on a small in-house interior design team and transformed it into a booming standalone business unit with global aspirations. Today, she leads not just product and design, but the future direction of the brand: expanding into hospitality, export, and property development, all while staying grounded in the brand’s core identity.

“I see myself as a steward of legacy,” Anna says. “My role is to carry this brand into the next 60 years, staying true to our values while thinking boldly about where we can go next.”

And of course, it’s no surprise that she’s an Enneagram 7, fuelled by possibility, guided by instinct, and not afraid to take calculated risks. For her, the Enneagram has become more than a self-awareness tool, it’s become a compass for aligned, courageous decision-making. “When I’ve had to take big leaps in my career, the Enneagram has helped me move through fear or doubt. It acts almost like a compass, nudging me toward decisions that feel aligned, even if they’re scary; it helps me know when to leap,” she says, “and when to slow down.”

Anna’s visionary nature is underpinned by balance with a team of Enneagram 1 energy, who bring structure to her fast-moving ideas. “It’s uncanny how often the people I work best with are natural complements to my type,” she reflects. “Knowing the Enneagram has enhanced how I lead, collaborate, and connect. It’s a tool for building powerful, well-rounded teams.”

To other women in business, her message is clear: Invest in yourself. “Working with the Enneagram and an executive coach through Caleo Consulting has been one of the most valuable investments I’ve made in my career. Personal growth and professional development are inseparable.”

Anna Weylandt is building a business that blends beauty and brains, instinct and insight, legacy and bold innovation. She’s proof that when self-awareness meets strategy, there are no limits to what’s possible.

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