TiedInsurer
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2) I already suggested that they reach CPF directly to check for employer side but they insisted that I do it myself (implying that I would be a self-employed/contractor status)
That's not how you determine if somebody is a contractor/self-employed. Generally, to be recognised as such, you need to provide the tools and equipment of your own trade. If they provide you with an office, and buy you a laptop for you to use, IRAS is unlikely to accept that you are self-employed. To qualify as such you would have to pay for almost all the things needed for you to do your work. Grab/foodpanda etc exploits this loophole by making their "workers" buy or rent their own transports, uniforms, bags etc. If you are misclassified, there will be penalties for your employer.
1) Tax implications?
2) A typical employer in Singapore will just factor 20% [Employee side] into the salary, and 17% [Employer side] usually company's admin/finance will take care --- If company wants me to contribute to CPF myself, does that mean they need to include all 37% of CPF into my salary, and thus every month I contribute accordingly myself as a self-employed?
1) You pay your own income tax. The company pays their own corporate tax. Unless you are somehow able to convince IRAS that you are a contractor, not a worker. Since you mentioned that you are the first employee here, who will be the company director? Singapore law requires that you have a local Singaporean director, so you can try proposing to be the director. Then the company can pay you no salary. Director fees only. You don't need to pay CPF on Director fees.
2) This one you would have to talk to the company yourself to know what their expectations are.....
Anyway, I'm a trained accountant, and am proficient with Singapore payroll, taxation and accounting. I also have experience dealing with secretarial matters, so there's that. If you need to hire somebody to work through these for you, I can offer my services. Just PM me. If you just have general questions, can just continue asking here or maybe make a new thread and I'll reply if it's simple enough, though i take no responsibility for all claims and representations I make here, and they do not constitute professional advice.
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