Milestone planning is the practice of defining specific time-bound accomplishments the company will achieve by defined dates. Examples: "$10M ARR by Q4," "100 enterprise customers by year-end," "Series B closed by month 18." It's used in capital planning (what milestones must we hit to justify the next round?), fundraising commitments, operational execution, and team alignment. Milestones are typically larger and longer-horizon than OKRs (quarterly objectives) and more outcome-focused than OKRs (which can include activity-based key results). It is the planning artifact that ties strategic direction to specific commitments and the document investors most want to see in fundraising contexts, because hitting milestones gener...