Realising that she and her sisters shared a passion for healthcare and the role that technology plays in making it more accessible in Southeast Asia, Cindy ventured into the insurance innovation space with Joanne’s support.

“I was lucky enough that Joanne and KSK group incubated me at the beginning, but those early days in the startup were gruelling,” Cindy recalls with a smile. “It was never a case of ‘You’re a family member, I trust you.’ There was a lot of pitching and heavy debate from the start, which I liked. In 2018, I went out to do our first external funding on my own. Joanne and the exco had said: 'You need to go find your own money if you want to do this'. It was gruelling but I wouldn’t trade it for anything else. My relationship with Joanne became much more collaborative after that. The whole experience of working together over the past five to six years has brought us closer together.”

Cindy proudly adds that Sunday secured a round of Series B funding at the end of 2021—a huge win for the insure-tech company as it aims to become a regional player in the coming years.  “I learnt a lot from our father as well as from Jo and Krys (Krystine)," Cindy says. "They are very experienced in their own fields and have gone through experiences very different to mine, so I'm grateful to be working with them. It’s nice to exchange notes between us every so often."

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Formerly a medical doctor who practised in parts of Africa and the UK, Krystine also worked as a consultant before assuming her current role as KSK Group’s director of strategy and head of KSK City Labs, the award-winning prop-tech arm of KSK Land.

“Leaving a career in medicine for prop-tech and real estate was a huge change, but one that I have no regrets making,” Krystine muses. “I worked as a doctor and then a consultant before joining KSK Group. Having that huge diversity and breadth in my career is an added advantage and so is having the opportunity to spearhead prop-tech development in KSK. Being able to help carve out the future of KSK Group and build a family legacy alongside my sisters is an incredible privilege that I don’t take for granted.”

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Looking back, Krystine recalls family vacations and dinners together as some of her fondest memories with her sisters, particularly the rare moments when they would all be in the same country together at once.

“Once I started working in the family business, the familial memories continued but I was exposed to the professional side of that relationship too, interacting with them as business partners and colleagues,” Kyrstine continues. “The nice part of that is celebrating huge business successes, like when Joanne and Cindy hit a round of Series B fundraising for Sunday. Obviously the entire family was proud, but being in the business with them, you get to see how much effort it took to get there and you’re able to celebrate those professional successes in a deeper way.”

The Rule of Three

An outsider to the sisters’ working and personal relationships may wonder if family issues ever get in the way of business or vice versa, or whether working with one’s siblings create a competitive edge.

“As a family, we understand each other on a personal level and we also understand what our strengths and weaknesses are. But we always draw a line. Family and home matters are separate from what you do in the office, that’s something that we built over time,” says Joanne, recalling instances when she had to conduct performance appraisals with her sisters and remain objective within a professional setting.

“I think it allows us to be more honest with each other and more vulnerable, and that’s ok," she adds. "In KSK, we practise psychological safety because we believe it’s important for team members to experiment and innovate, yet feel safe enough to fail and start reiterating again when they do.”

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While the personal and professional boundaries rarely overlap for the sisters, there is one aspect that unites both sides: “The strength of a family business is really the family values that don’t change,” says Joanne. “Those are the same values in life that we carry in our professional careers. Those same family values translate into the KSK values that we inculcate in the entire company.

“When challenges get thrown our way, it’s tempting to want to change our values just to succeed,” adds Krystine. “But working together with siblings and with our father means that we can check each other and say, 'that’s not who we are, these are our values, this is who we want to be in this world and in this company as well'.”

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