The Employment Pass comes through, and suddenly you’re a Singapore employer. The incorporation paperwork is behind you, the bank account is open, and — for the first time in months — you can think about actually building a team.
That’s usually when founders come to me. The company is set up properly, they’re proud of it, and they’re about to post their first job. I ask a few questions. The expression changes.
Because the space between company incorporated and first employee on payroll is the bit no one seems to prepare founders for. It’s not incorporation — that problem is well-covered by corporate services firms. And it’s not yet “HR” in the way a scale-up thinks about HR. It’s the gap in between. And the decisions you make here are the ones that tend to come back and bite you eighteen months later.
Here’s what I’d tell a founder who’s just had their Singapore Employment Pass approved and is about to make their first hire.
1. Your Singapore employment contract is not a template exercise
I’ve seen founders download a Singapore employment contract template, change the names, and sign it. Sometimes the template is decent. More often it was written for a completely different kind of business, contains clauses that don’t apply to you, and is missing the ones that do.
The things most templates get wrong, in my experience: probation periods that are either too short to be useful or too long to be enforceable; notice periods that don’t match what you’d actually want in a resignation situation; confidentiality language that wouldn’t hold up if it ever mattered; and IP assignment clauses that are either absent or so broad they’re effectively meaningless.
The Employment Act sets the floor. Your contract is where you decide what to build on top of that floor. It’s worth getting right once, properly, rather than fixing it retroactively when something has gone wrong.
2. Understand CPF before your first payroll run, not after
CPF isn’t optional for Singapore citizens and PRs, and the rates depend on the employee’s age and wage. That part is straightforward if you read the CPF Board website. What’s less obvious is that CPF also affects how you think about total compensation, what you can and can’t claw back if someone leaves, and how you structure things like bonuses and allowances.
Founders who come from jurisdictions without equivalent schemes often assume CPF is “just another payroll tax.” It isn’t. It’s a significant structural feature of hiring in Singapore, and getting your head around it before you’re running your first payroll saves a surprising amount of cleanup later.
3. MOM compliance isn’t a one-off event
When you hire your first employee, you become an employer under Singapore’s Ministry of Manpower. That triggers obligations — not huge ones, but real ones — around record-keeping, payslip issuance, working hours, leave entitlements, and statutory reporting.
None of this is complicated individually. The problem is that nobody warns you it’s cumulative. Each small obligation on its own is easy to absorb. Taken together, they’re enough to catch out a founder who’s trying to do everything themselves while also running the business.
4. Decide what you’re not going to do in-house
This is the decision that distinguishes founders who enjoy building a team from founders who end up resenting the admin.
Payroll, CPF filings, employment contract drafting, leave tracking, grievance handling, performance reviews — these all have to happen. The question isn’t whether you do them, it’s whether you do them yourself, hire someone to do them, or work with someone external.
For most founders making their first hire, doing it all yourself is the wrong answer. You didn’t start a company to administer CPF contributions. Hiring a full-time HR person for a team of three is also the wrong answer — the economics don’t work. The sweet spot, for the first year or two, is usually fractional or outsourced support that scales with you as you grow.
That’s what we do at Expert People Solutions, and it’s why the conversation usually comes up right around the first-hire moment. Not because we sold someone on it — because the founder hit the gap and realised there was one.
5. The cultural decisions matter more than the compliance ones
Compliance is table stakes. You have to get it right, but nobody ever built a great company purely on compliance.
The decisions that actually shape what your company becomes are the ones nobody puts in a checklist. How do you onboard someone properly when you’ve never done it before? What does your first team meeting look like? How do you give feedback to the first person you’ve ever managed in a company you own? How do you handle it when a hire isn’t working out — kindly, legally, and quickly?
These are the questions that feel too early to ask when you’re still getting the EP sorted, and too late to ask when the problem is already in front of you. The best time to think about them is the gap in between — right after your EP is approved, and before the first hire walks through the door.
The bit nobody tells you
If I had one piece of advice for a founder who’s just had their EP approved and is about to hire, it would be this: spend a week, not a day, on the things that happen before the first person starts.
Write the contract properly. Understand CPF before you run payroll. Set up your record-keeping so it doesn’t become a retrospective cleanup job. Decide what you’ll do yourself and what you’ll outsource. And most importantly, think about the kind of company you want to build before you start building it, because the early decisions set patterns that are much harder to change later.
That’s the gap. And founders who take it seriously tend to have an easier run through the next eighteen months than founders who don’t.
If this resonates and you’re approaching your first hire in Singapore, have a look at expertpeoplesolutions.com — we do fractional HR for startups and SMEs at exactly this stage. Happy to have a conversation.
