Eileen Willett: Giving Women Confidence through Luxurious Clothing

Insights Success
4 min readMay 22, 2021
Eileen Willett | Co-Founder | Cucumber Clothing

Leadership is almost always associated with strength, force, power and ambition — all traits that translate easily to the battlefield, believes Eileen Willett, the Co-Founder at Cucumber Clothing. According to Eileen, these important traits should be possessed by every leader, but equally important are those of empathy, emotional intelligence, integrity, vision and humility. The combination of all these traits together allows for a rounded leadership, one that allows for the strength of dissention, resilience in the face of discord and ultimately success of the team as a whole.

In an interview conducted between Eileen and Insights Success, he sheds light on her entrepreneurial journey and how she headed Cucumber Clothing to reach where it is today.

Below are the highlights of the interview:

How do you diversify your organization’s offerings to entice the target audience?

At Cucumber, we are proud for what we stand for, this includes our strong commitment to sustainability and our support for women at all stages of their lives. We believe this can be seen in our dedication to customer service that encompasses personal follow ups to all enquiries, as well as ensuring that the products we offer are the ones our customers want. We do this through constant attention to where our sales lie, as well as reaching out to our wonderful customer base by email, social media and focus groups.

What roadblocks or challenges were faced by you in a corporate business? And how did you overcome them?

Every business faces multiple stumbling blocks, from the small irritations of an email being bounced back to more serious ones that affect customers or cash flow. We have had our fair share of challenging moments. One of the most serious was our first foray into outsourcing fulfillment. At great cost we moved all our stock to a distant warehouse and entrusted a fulfillment company to send out our orders.

With strict instructions as to how to pack, how to label to try and ensure a seamless continuation of our five star customer service we were dismayed and then horrified to find that customers were receiving the wrong items, double orders and some orders marked ‘shoes’ (we do not make shoes.) We quickly moved back in house, lesson learned.

According to you, what essential traits should a business leader possess to thrive in any given competitive market?

The world of business shares some characteristics with the world of academe. With a goal to achieve (read thesis) one of the key supports is the undertaking of deep and serious research. These investigations must cover competitors, data analytics, new material and manufacturing technology, the latest social media and online technology to name but a few areas. A keen interest in facts and figures is an absolute essential for a successful business leader. Working in vacuum is not realistic, however brilliant an idea may be, it has to reside in the real world.

Where are you focusing your energy now, and where do you hope to make an impact next?

The background to business of the last twelve months has been one of chaos and bewilderment, to put it mildly. No sector has been untouched and fashion and retail have been on a what feels like a high speed roller coaster ride. With this in mind we have spent much of the past year focusing on the consolidation and reorganization of our business to ensure that as the world begins to open up, we will be ideally placed to benefit. Right now we are focusing our energies in creating new supply lines, accelerating the widening of our routes to market and investing in marketing. We aim to continue increasing our market share nationally and internationally.

What is your idea of impactful leadership? What style of leadership do you personally prefer and have implemented within your team at Cucumber Clothing?

Following on from leadership traits above, for me personally, impactful leadership is a troika led by inspiration, vision and emotional intelligence. A leader must have the original vision. This is what every cog in the business ultimately is working towards achieving. A successful leader must also be able to inspire passion for this vision, both within themselves and their team. Finally, a business is a community. How we treat and interact with those within that community will always play a major role in how that community functions. To be able to lead, to be able to have an impact as a leader, draws on deep wells of emotional intelligence. A leader must be able to gauge and understand each employee’s strengths and weaknesses. They must be able to utilise the former and improve the latter. What is emotional intelligence other than a type of kindness? An acknowledgement that we are all different and all have a role to play. A true leader is understands this instinctively.

What have you envisioned for your organization’s future, with regards to your role at Cucumber Clothing and for your personal ambitions as well?

At Cucumber we are keen to be recognized as a brand leader in sustainable, luxury leisurewear that empowers women. Quite a mouthful, but we have been ploughing all our energies into making this happen and feel we have come a long way since our launch only three years ago. On a personal note, I am very keen to become more involved in leveling the playing field for those of a diverse background entering the start-up world. I am a featured member of i:Entrepreneur, a campaign celebrating, championing and shining a light on small businesses founded by entrepreneurs of diverse backgrounds; a founding member of the Allbright Diversity and Inclusion Committee, as well as a shortlisted candidate for the 2020 Asian Women of Achievement Awards. Finally, after a year of global turbulence, what I really wish for is a future of peace where we can spend time with those we love and hug them once again.

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