Start with value metrics—the knob users gladly pay for. Seats, tracked events, projects, or revenue processed work better than arbitrary limits. Map 2–3 tiers to clear segments: starter (self-serve), growth (team), and scale (procurement). Avoid feature gating basics like security; gate advanced automation, analytics, or support levels.
Choose a price architecture: flat + overages for usage metrics, or tiered with seat-based multipliers. Publish pricing transparently; hide only bespoke enterprise terms. Offer annual discounts to improve cash flow and signal commitment, but keep monthly for low-friction trials.
Design upgrade paths. In-app prompts should highlight the specific limit hit, estimated new cost, and immediate benefit. Make downgrades painless to build trust. Add trial extensions for high-intent users rather than steep discounts. Use per-seat minimums cautiously; they can harm team adoption.
Experiment systematically. A/B test headline price, trial length, and packaging—not all at once. Track activation, expansion, churn, and payback period. Interview closed-lost deals to learn willingness to pay. Revisit pricing quarterly; small changes compound.
Rollout without backlash. Grandfather existing customers for a grace period, communicate early, and offer migration helpers. Pair price changes with clear product improvements. Keep billing accurate: proration, taxes, invoices, and dunning must be reliable or you will lose trust.