There’s a natural inflection point in most startups. When you’ve got 5 to 10 people, HR is informal. It’s founder-led. People know each other, decisions get made in conversation, culture is osmotic. It feels like it could stay that way forever.
Then you hit 15 to 20 people and something shifts. You’ve got different experience levels, different seniority, different compensation. People have different roles in different parts of the business. Culture is no longer naturally cohesive. It needs to be intentionally maintained. Leave requests are frequent enough that you need a process. You’re making hiring decisions fast enough that an ad-hoc approach starts causing problems.
This is the critical window. The HR foundations you establish at 15 to 20 people shape how your organisation operates at 50, 100, and beyond. Get them right and the rest scales relatively smoothly. Get them wrong and you’ll be untangling the mess for years.
Employment Contracts That Actually Work
It’s surprising how many companies at 15 to 20 people are still using dodgy employment contracts. Downloaded templates, contracts that haven’t been updated for years, contracts that don’t properly address intellectual property, non-competes, or termination.
This matters. A poorly drafted contract can create liability. It can be ambiguous when things go wrong. It can fail to protect your IP or constrain key people from leaving and starting a rival firm. And in Singapore, where employment law has specific requirements around notice periods, leave entitlements, termination, CPF contributions, and PDPA compliance, a template that works in the UK or Australia won’t be robust here.
You don’t need to go overboard. You’re not running a multinational. But you do need contracts that are properly drafted for Singapore, that reflect how you actually employ people, and that include provisions around IP, confidentiality, notice periods, and termination. This costs a bit of money upfront, but it’s a one-time investment. A good set of template contracts that your lawyers have reviewed will serve you through your first 100 employees.
The right time to do this is now. Before you hit 20. If you’re at 20 already and you haven’t done it, do it this quarter. The cost of fixing a contract mess after you’ve hired 30 people is significantly higher than doing it before.
A Compensation Philosophy
You don’t need fancy salary bands and market benchmarking at 15 people. But you do need a view on how you pay people. How does someone move from level one compensation to level two? What drives increases? How do bonuses work, if you offer them? Are you positioned as a market-rate payer, a premium payer, or a startup-stage discount payer?
Without clarity here, inconsistency happens. One person gets a 10 per cent raise because you thought they deserved it. Another gets five per cent because you couldn’t afford more. One person knows exactly what it would take to get a promotion and bonus. Another has no idea how their compensation is determined. And then at 25 or 30 people, someone compares notes with a peer, realises the inequity, and either leaves or becomes resentful and less productive.
A compensation philosophy doesn’t have to be complicated. It might be something like: “We pay at market rates for the Singapore market, adjusted slightly down for startup stage. Increases are performance-based and annual. Bonuses are tied to company performance and personal contribution.” Written down, communicated, and consistently applied.
If you can articulate why someone is paid what they’re paid and how they can expect compensation to evolve, you’ve solved half the compensation headaches that plague growing companies. Most founders don’t do this because it feels premature. It’s not. It’s exactly the right time to establish it.
Feedback and Performance Management
The absence of any structured performance approach is the single biggest source of people problems in scaling startups. Someone’s not performing. Nobody’s ever told them this clearly. When you finally have to confront it, they’re shocked and defensive because they had no framework for understanding how they were doing.
You don’t need a formal annual review cycle at 15 people. That would be overengineered. But you do need consistent goal-setting, regular check-ins, and a clear framework for addressing underperformance.
What does this actually look like? At the start of a quarter or project, you sit down with each person and clarify what success looks like. What are they trying to achieve? What does good look like? What support do they need? Then you check in regularly. Monthly or as part of a natural rhythm. You acknowledge what’s working, you course-correct on what isn’t. And if someone’s struggling, you’re having that conversation in real time, not storing it up for an end-of-year reckoning.
When something goes wrong and you need to have a difficult conversation, it’s a natural continuation of what you’ve already been discussing, not a shock. And when things are going well, people know it because you’re saying it.
This is equally applicable whether you’ve got formal goal-setting or you’re working more fluidly. The principle is the same: clarity about what good looks like, regular feedback, and addressing issues when they emerge. The companies that do this well have much higher retention and better performance. The companies that don’t, don’t.
Clear Policies on Leave, Flexible Work, and Basics
Singapore’s Employment Act sets minimums: annual leave, sick leave, maternity leave. Your policy should meet these minimums as a floor, not a ceiling. And you should have decided what you’re offering beyond the minimum.
Are you offering flexible work? If so, how does it work? Can anyone request it, or is it role-dependent? Do you allow remote work? If so, is it any day or structured? Can people compress hours or are you focused on output rather than presence? What does your parental leave actually look like: statutory minimum or something more generous?
Again, you don’t need a 50-page handbook. But you do need clarity. People want to know what’s possible and what the norms are. If you leave it ambiguous, different people will take different liberties, and you’ll end up enforcing inconsistently.
This also shapes your employer brand. If you’re generous with flexible work and parental leave, that’s a genuine competitive advantage in Singapore’s talent market. If you’re at the minimum on everything, that’s also fine. But be transparent about it. What kills trust is ambiguity or inconsistency.
A Hiring Process That Actually Scales
When you’re hiring one or two people a year, you can wing it. When you’re hiring eight to ten, you need structure. Structure means defined roles with clear job descriptions, a consistent set of interview stages, specific interview questions, and a defined evaluation framework.
This sounds heavy for a small company, but it doesn’t have to be. It can be simple: stage one is a screen of CVs against the job description to check basic fit. Stage two is a 30-minute first interview with someone from the team or the founder, focused on understanding their background and motivations. Stage three is a technical or work simulation relevant to the role. Stage four is a conversation with the person the hire will report to or work closely with. That’s it.
What matters is consistency. You’re evaluating each candidate against the same criteria. You’re asking similar questions. You’re documenting your thoughts. And you’re making decisions based on evidence, not gut feel.
The companies that get this right make faster hiring decisions, attract better candidates (because the process feels professional), and have fewer mis-hires. The companies that don’t spend months on hiring, settle for mediocrity, and then spend even more time managing people who aren’t doing the job.
Basic Visibility on Your People Data
You don’t need a fancy HRIS at 15 people. But you do need to track headcount, compensation, leave, and basic performance information somewhere. A well-organised spreadsheet is fine.
Why? Because it helps you make better decisions. You can see compensation distribution and catch inequities. You can track leave and ensure people are actually taking it. You can see performance trends across the team. You can see who’s at risk of leaving because they’re not developing. You can identify skills gaps and plan hiring accordingly.
Most founders manage this informally in their head. And it works until it doesn’t. Until you realise three months later that someone needed support and you didn’t see it. Until you’re surprised by who’s left or who’s struggled. Until you’re making compensation decisions based on gut feel rather than data.
A basic spreadsheet with headcount, role, start date, compensation, leave taken, and a brief performance or development note per person gives you visibility. It’s five minutes a month to keep current. The insights it gives are disproportionate to the effort.
The Cost of Getting Ahead of This
Here’s what’s important to understand: getting these foundations in place at 15 to 20 people is not expensive. An employment lawyer can draft solid template contracts for a few thousand Singapore dollars. A compensation philosophy takes a weekend of thinking with your co-founders. A performance management approach costs nothing. It’s just being intentional about how you have conversations. A hiring process is free. A spreadsheet is free.
The cost of not doing it, though, gets paid over and over. At 50 people, you’re untangling compensation inconsistencies that have built up over years. You’re dealing with people problems that could have been prevented by better feedback early on. You’re hiring chaotically because you never established a process. You’re dealing with employment law challenges because your contracts weren’t built for Singapore.
This is genuinely one of the highest-ROI investments a founding team can make. Do it when you’re at 15 to 20 people.
You don’t need a full-time HR director at this stage — that would be over-engineered and expensive. What you need is senior expertise on demand: someone who’s done this before, knows Singapore employment law inside out, and can get it right quickly without the overhead of a permanent hire. That’s precisely what fractional HR is designed for.
If you want to get started quickly and handle most of it yourself, the HR Starter Pack (SGD 299) gives you the core documents and frameworks — employment contracts, a basic handbook, onboarding templates — in a practical, self-guided format built for Singapore. If you’d prefer a full picture of where you stand first, the HR MOT is a structured diagnostic that identifies your gaps and maps out exactly what needs to be done. Either way, get in touch if you’d like to talk it through.
