Capability 2 · Company System
Chart the Path
Three funding options looked totally different on paper, but the leadership team realised every path required the same thing: stronger unit economics and cash discipline.
Founders say
“We set OKRs every quarter, but if you asked my designer how her work ladders up to the raise, she couldn't tell you. Honestly, half the time neither could I.”
Where you are today
- Goals get set each quarter, but no one can trace their day-to-day work up to the next milestone.
- "What good looks like" for the raise is a number you picked, not one your investors would recognise.
- OKRs measure activity — tickets shipped, calls made — instead of outcomes that move the company.
Where you’re headed
- One page connects every team's quarter to the next milestone, and back to the mission.
- You know what makes the next round a hell yes — because your investors, the market and you all defined it.
- Anyone in the company can explain how this quarter's work moves a company goal.
Why this matters
This is where you flip from the aspirational and long-term to what matters now. Most companies run on a rhythm, and for many that rhythm is the funding round — so the next milestone is what everything else has to serve. The discipline that connects it all is OKRs: objectives that are ambitious, key results that measure outcomes rather than inputs (Andy Grove's idea, made famous by John Doerr in Measure What Matters). Done well, the whole company fits on one page — and everyone, from support to design, can see how their work ladders up to the milestone and the mission.
What this means
- Set the next big company milestone — often a funding round — and define what good looks like.
- Cascade it into long-, medium- and short-term OKRs so teams know how their work contributes.
- Write OKRs that measure outcomes, connecting the North Star Metric to supporting KPIs and team goals.
What good looks like
- A clear picture of the next milestone and what "good" looks like — defined with your investors, your market and yourself, not in a vacuum.
- Goals that cascade: long-, medium- and short-term OKRs that each ladder up to the milestone.
- OKRs that measure outcomes, are ambitious and measurable, and that everyone can connect their own work to.
Where founders get it wrong
- Setting the next-round bar alone, so your investors don't actually share your definition of success.
- OKRs that measure inputs and activity instead of outcomes — or vanity numbers no one can act on.
- A plan only the leadership team understands, so most of the company can't see how they contribute.
Start with the next milestone
Begin with the next big milestone for the company. Often this is a funding round, because that's the rhythm you operate by — but it could be a launch, a new market, or profitability. Whatever it is, define what good looks like: ask your existing investors what would make the next round a hell yes, map the opportunities and threats against your peers and the competition, and ask yourselves. Fold those into one concrete picture, then work backwards and cascade it down.
Credit: Outstride original
Write OKRs that actually connect
- Objective plus key results — a direction paired with the measures that prove you got there.
- Measure outcomes, not inputs: results that moved, not effort that was spent.
- Set them ambitious, keep them measurable, and make sure they make sense together.
- Cascade so everyone connects: support, design, engineering — each person can see how their work moves a company goal, toward the milestone, toward the mission.
The test of a good path: a founder should be able to express the most important things about the company in a single one-page document — the long-term goal, and the pieces you need to gather to get there — clearly, concisely and enthusiastically.
One more piece: pick the single metric the whole company maximises, guarded by the health metrics that must not slip. That's your North Star — and once the quarter is running, report against the plan with a simple red-amber-green status rather than narrative updates.
What you can do right now
- Define what good looks like for the next milestone. Ask your existing investors, independently, what would make the next round a hell yes. Line their answers up against your peers and the market, and your own view. Turn it into a concrete bar — e.g. 10,000 paying users, strong activation, CAC under €30. CEO Test →
- Work backwards and cascade. From that bar, set long-, medium- and short-term OKRs so each layer clearly leads to the next milestone. OKRs →
- Pressure-test every key result. For each one ask: is this an outcome or an input? Rewrite anything that measures effort into something that measures result.
- Run the one-page test. Can you explain the long-term goal and the pieces you need to get there, clearly and enthusiastically, on a single page? If not, it isn't sharp enough yet. Strategy One-Pager →
The toolkit
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