The first employee HR checklist

A first employee changes a company’s legal position overnight. The day someone accepts an offer, a company that has never issued a payslip in its life owes Key Employment Terms, an itemised payslip, possibly CPF and SDL, and, depending on the role, compulsory insurance that has to be arranged before that person’s first day, not on it. None of this is optional or scaled to company size. It applies identically to employer number one hundred and employer number one.

Start with the figure most guides still get wrong. Paternity leave in Singapore is four weeks, not two, for any birth from 1 April 2025 onward: it doubled from the previous two-week entitlement, and a striking amount of still-circulating content has not caught up. It is one line in a longer checklist, but it is a useful test of whether the source you are reading is current.

This checklist sits inside the fuller sequence in the first 90 days of HR and payroll in Singapore; here the focus narrows to exactly what a first employee makes true, and when. What follows is organised the way these obligations actually arrive: what has to be arranged before day one, what starts on day one itself, what is due within the first month, what runs continuously from day one onward, and what phases in as service accrues.

Before day one

Work Injury Compensation insurance is the one obligation with a real lead time, and it has to be arranged before an accepted offer’s start date, not during the first week. It is compulsory for any employee doing manual work, regardless of salary, and for non-manual employees earning S$2,600 or less a month (basic salary, before overtime, bonuses or allowances), covering local and foreign staff alike. MOM’s own instruction is to finalise the policy and hand insurers the required information at least 21 days before it needs to start. Unlike the Auto-Inclusion Scheme, which only bites at five employees, or the advertising rule under the Fair Consideration Framework, which exempts companies under 10, WICA has no headcount threshold at all. It applies from employee number one, and failing to insure a required employee carries a fine of up to S$10,000 and/or up to 12 months’ jail, on top of the employer remaining personally liable to pay a valid claim regardless of whether cover existed.

The other before-day-one task is simpler and easier to skip: have a Key Employment Terms template and a leave policy ready to go before an offer is signed, not drafted from scratch once the clock on issuing them is already running.

On day one

Coverage under the Employment Act starts the moment someone begins work, and it covers almost everyone: any person under a contract of service with a Singapore employer, regardless of nationality, with a short and specific exclusion list, seafarers, domestic workers, and employees of the Government or a statutory board, each covered instead by their own separate legislation. Itemised payslips and Key Employment Terms apply to every employee the Act covers, including managers and executives who sit outside Part IV’s narrower hours-of-work and overtime protections. A manager on a healthy salary still gets a full itemised payslip; that requirement does not scale down with seniority.

An itemised payslip is due with the very first payment, or within three working days if it cannot go out with the payment itself. If the new hire is a Singapore Citizen or Permanent Resident earning more than S$50 a month, CPF becomes payable from that first month of wages, and SDL applies regardless of citizenship, for every employee working in Singapore, with the registrations that make both possible covered in setting up payroll for your first employee. Neither obligation is deferred to a later date; both start on the wages for day one. The item lists and deadlines for both payslips and Key Employment Terms are covered in full in itemised payslips and Key Employment Terms for Singapore employers; this checklist covers when each one first bites, not what goes on the form.

The eleven gazetted public holidays also apply from day one, as a standing entitlement separate from annual leave. They cannot be deducted from an employee’s leave balance, and an employee does not need to accrue any service before a public holiday applies to them.

Within the first month

Key Employment Terms, in writing, are due within 14 days of the first day of work, for any employee on a contract of 14 days or more. That is a one-time obligation per employee, distinct from the itemised payslip that recurs with every payment. Miss the 14-day window and the same administrative penalty framework applies as for itemised payslips: MOM’s stated approach on a first lapse is to engage and guide the employer to fix it within a month, escalating to an administrative penalty of up to S$400 per repeated infringement after that. Fourteen days sounds generous until it lands in the same fortnight as onboarding, a client deadline, and someone’s annual leave.

Ongoing, from day one

Employment records are not a one-time filing; they are a running file that starts the day someone joins and never quite finishes. The rule is to keep personal particulars, salary, leave taken and public holidays observed for at least two years for current staff, and a former employee’s last two years of records for at least a year after their last day. Nobody asks to see it until an audit, a dispute, or an inspector does, and reconstructing eight months of leave records from memory at that point is exactly the kind of task a first-time employer discovers too late is unpleasant. It costs nothing to keep this in the same spreadsheet as the payslip data from day one; it costs a genuinely bad afternoon to rebuild it later.

What phases in from three months of service

A block of statutory leave entitlements only starts once someone has three months of continuous service, and they are worth setting expectations on before an offer is even made.

Annual leave begins at 7 days in the first year of service, rising by a day for each additional completed year, capping at 14 days from the eighth year onward. Sick leave and hospitalisation leave phase in on the same three-month clock but by month of service: 5 days outpatient and 15 days hospitalisation at 3 months, rising to 8 and 30 at 4 months, 11 and 45 at 5 months, and the full 14 days outpatient and 60 days hospitalisation, which includes the outpatient allowance rather than stacking on top of it, from 6 months onward.

Maternity leave sits apart from all of this, and it is worth stating plainly, because most checklists compress it into “16 weeks, paid” without the actual mechanics. Eligible mothers receive 16 weeks of Government-Paid Maternity Leave, but that is not an Employment Act entitlement at all; it runs under Part 3 of the Child Development Co-Savings Act, gated on the child being a Singapore citizen rather than on the parent’s status, alongside the mother having at least three continuous months of service before the birth. For a first or second child, the employer pays the first 8 weeks at the employee’s gross pay and the government reimburses the last 8, capped at S$10,000 per 4-week block; from a third child, the government funds all 16 weeks under the same cap. Where the child is not a Singapore citizen, a lesser Employment Act fallback applies instead, 12 weeks, with 8 paid if the mother has fewer than two other living children.

Paternity leave runs on the same three-months-of-service condition and the same child-citizenship gate, and it is where this checklist opened: 4 weeks of Government-Paid Paternity Leave for births from 1 April 2025 onward, doubled from the 2 weeks that applied before that date. The father also has to be lawfully married to the mother, between conception and up to 12 months after the birth.

The checklist, at a glance

Obligation	What it requires	When it first applies
Key Employment Terms	Written terms covering pay, hours, leave and notice (18 items)	Within 14 days of the first day of work
Itemised payslip	12 mandatory items with every payment	With the first payment, or within 3 working days
CPF contributions	Payable for Citizens and PRs earning more than S$50 a month	From the first month of wages
Skills Development Levy	Payable for every employee, foreign staff included	From the first month of wages
Work Injury Compensation insurance	Compulsory for manual work at any salary, or non-manual work at S$2,600 or less	Arranged at least 21 days before the start date
Public holidays	11 gazetted days, separate from annual leave	From day one
Annual leave	7 days, rising to 14 by the 8th year	After 3 months of service
Sick and hospitalisation leave	Phases from 5 and 15 days to 14 and 60 days	From 3 months, in full from 6 months
Maternity leave	16 weeks GPML if the child is a Singapore citizen	After 3 continuous months of service
Paternity leave	4 weeks GPPL for births from 1 April 2025	After 3 continuous months of service
Employment records	Current staff: last 2 years. Former staff: their last 2 years, kept 1 year after departure	Ongoing from day one

None of this scales with headcount. What changes as a company grows is not whether these obligations apply, since they all started with employee one, but how much of a burden they become to track without something like the payroll compliance calendar or a system built for it, alongside the earlier registrations covered in company registration versus HR readiness. A first hire is also the moment a company has to decide whether to hold HR set-up in-house or bring in help getting it built properly. Whichever way that goes, the paternity figure is not a matter of opinion: four weeks, not two, dated from 1 April 2025.