A good hiring plan starts with one question: who do we need, and by when, to hit the milestones we’ve committed to? Most companies do it the other way round. They draw the org chart they want in eighteen months and fill in the boxes from there.
Start with your milestones
Most of the milestones in a scale-up are fixed. A delivery date is in the customer contract. The launch or international expansion is in the board plan. And your next round or budget depends on the numbers you’ve promised.
So before you think about roles, write down your milestones for the next twelve months. Next to each one, note which skills and competences the team needs to be successful. Think in capabilities, such as closing enterprise deals or setting up a finance function.
Then hold that list against the team you already have. Some of those skills may already be there, or could grow with some training. The gaps that remain are what you need to hire for. Only then do you turn them into roles and job titles.
Put the roles in the right order
Every growing company has more roles on the wish list than it can fill at once. So you need an order, and that order should follow your milestones.
I ask three questions before opening a permanent vacancy:
- Will the work still be there in eighteen months? If it’s tied to a project or a short period, it goes to an interim or a project contract.
- What is its impact on revenue or a committed milestone?
- How many other projects or people depend on it?
The first question decides the type of contract. The other two decide the order. A role with a direct impact on revenue that others are waiting on comes first, because leaving it open slows down everything behind it. A role that scores high on only one of the two can wait a little. A role that scores low on both is a nice-to-have.
Getting your budget approved
A list of job titles with salaries is the fastest way to lose your hiring budget. The CFO sees the total, not the value, and starts cutting.
Change the conversation. Present every role as a line that connects cost to outcome: what the role costs per year and which milestone or revenue it protects. Then add what a three-month delay would cost. A board will happily debate a headcount. It’s much harder to debate “without this hire, our biggest client goes live a quarter late”.
A board will happily debate a headcount. It’s much harder to debate “without this hire, our biggest client goes live a quarter late”.
If you’re a founder, the same applies to your investors or your board. They don’t expect you to hire everyone at once. They expect you to know which hire moves which milestone.


