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Two women entrepreneurs on how they tackled tradition and gender biases to transform their businesses

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Jenny Tay and Clare Leighton share one thing in common: they are women leading their respective small and medium-sized enterprises (SMEs) – Direct Funeral Services and fileAI, respectively – and who refined business operations in their sectors, introduced innovation and challenged longstanding industry norms.

Both told their stories at UOB’s womenpreneur panel discussion held at the National Gallery Singapore on Apr 11.

Direct Funeral Services

Just over a decade after taking over the family business, managing director Jenny Tay and her husband, Darren Cheng, its chief executive officer, instituted wide-ranging changes at Direct Funeral Services.

Business Time Article Jenny Tay - Two Women Entrepreneurs On How They Tackled Tradition And Gender Biases To Transform Their Businesses
With their lives inextricably linked to their work, Jenny Tay and Darren Cheng decided on a casket as a prop for their wedding photos. PHOTO: JENNY TAY

The company was set up in the 90s by her father, Roland Tay, who is well-known for offering pro bono funerals for the underprivileged and victims of tragic, high-profile murder cases. He handed over the management reins to his daughter and son-in-law, but still plays a role manning the company’s customer hotline.

In 2013, the young couple stepped into the business “out of love”, inspired by the elder Tay’s commitment to helping others.

But their early days were not easy. They came up against resistance from industry veterans, who asked why a well-educated woman like Jenny Tay would enter what they saw as a “dying trade”.

The couple set out to challenge outdated perceptions. Their first step was to professionalise the team by introducing uniforms, streamlining the workflow and elevating the standard of service.

Though change did not happen overnight, Jenny Tay noted that the company’s staff felt that they came to be accorded more respect by their clients, who even addressed them by name.

Since taking over, the couple have introduced personalised memorial biographies for their clients, Jenny Tay told The Business Times on the sidelines of the panel discussion.

These biographies are generated by an in-house-developed artificial intelligence (AI) platform that creates the life stories of the deceased – shifting the focus at wakes from how someone died to how they lived.

Direct Funeral Services started out writing each biography from scratch, but as demand for these memorial biographies grew, AI enabled them to offer this service at scale. Families furnish the key details, and the system comes up with the life stories that are shared at wakes and memorials.

Jenny Tay said that the AI-assisted biographies reduce the emotional strain on the deceased’s family of facing repeated questions from visitors at wakes. This enables visitors to connect with the person’s legacy in a more meaningful way. (*see amendment note)

A tech innovation introduced in March was the Memory Weave app, through which guests at wakes and memorials contribute photos and videos of the deceased as a digital gift to the family. These go on show on a monitor at the funeral.

Another innovation is the use of therapeutic music through a collaboration with the Teng Ensemble, a Singaporean Chinese fusion music group, to support individuals coping with grief. Jenny Tay was inspired after attending one of the group’s concerts, where binaural beats were woven into their compositions to ease anxiety. This method is already being used in hospitals and eldercare homes.

“It sparked in me that we can use that for our grieving families,” she said.

Following studies with higher learning institutions, Direct Funeral Services will incorporate monaural beats – suitable for open settings like wakes – into its funeral music. The result is a calming soundscape that helps the bereaved process emotions more naturally. This will be launched by August.

The couple also went on to found Direct Life Foundation, the charitable arm of Direct Funeral Services which supports vulnerable seniors and underprivileged children through community care.

Direct Funeral Services has undergone significant growth and transformation since 2013, expanding from a five-person team to a staff of 80. Once largely made up of workers in their 40s to 60s, the team now comprises mainly younger professionals in their 20s to 40s.

They have seen a fifteenfold increase in revenue since 2013, the managing director said.

“Our people find the work meaningful,” Jenny Tay said. “With our commitment to raising service standards in the industry, we’ve earned the trust of families – many of whom return to us because they believe in what we do.”

FileAI

Leighton, co-founder and chief operating officer of fileAI, did not face the challenge of bringing a traditional business up to date like Tay did, but said she had to contend with other biases.

Set up at the height of the Covid-19 pandemic, the Singapore-based startup was the result of integrating AI and machine learning to better manage documents and information.

Leighton said the idea for the business came from a pain point she experienced first-hand, when she had to get a large volume of documents organised.

FileAI uses a combination of off-the-shelf and proprietary AI to automate the extraction and processing of unstructured data – imposing organisation on the data found in, for example, PDFs, spreadsheets and e-mails. It helps businesses streamline high-volume workflows across industries such as finance, insurance and supply chain operations.

She told The Business Times: “We felt it acutely. During the lockdown, when early customers weren’t drawing revenue, they were still willing to subscribe and pay for a product they couldn’t even see. That kind of validation gave us the confidence to keep building (the business).”

The Australian’s journey into tech began in 2016 at a fledgling Uber, at a time of its rapid growth.

“Uber (at that time) was a great case study and cautionary tale for companies that do not properly address diversity and inclusion early, also with leadership and development,” she said.

She said that during Uber’s hypergrowth phase, promotions happened rapidly – leading to unconscious bias and systemic issues in hiring.

“We talk about it now as ‘cookie-cutter hiring’. The thinking was: ‘Did they go to the same university… have the same degree?’ It was hiring done in your own image, and it stifled diversity and innovation,” Leighton said.

These experiences shaped her approach to leadership at fileAI. She believes in removing the so-called “gender lens” that typically frames women’s stories around identity, rather than their capability.

While she acknowledges the challenges of being a woman in tech, she is careful not to overemphasise gender in evaluating success.

Leighton said: “A lot of my mentors, a lot of the growth and opportunities I was given, were merit-based, and it was with men in the room or men leading me. So while we need more female leadership, it is limiting to think we need only women mentors.”

Just five years since its launch, fileAI now operates in 18 countries, with teams in five of them. The company has grown steadily and, as at February this year, raised US$14 million in a Series A funding, further cementing its place in the AI-driven productivity space.

This article is adapted from “Two women entrepreneurs on how they tackled tradition and gender biases to transform their businesses”, originally published by The Business Times on 23 April 2025.

Two women entrepreneurs on how they tackled tradition and gender biases to transform their businesses

Featured Image For Two Women Entrepreneurs On How They Tackled Tradition And Gender Biases To Transform Their Businesses

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