You can always grandfather existing users into their current pricing while raising prices for new users.

Consider offering a discount for commitment, such as 10-20% off for annual subscriptions, to encourage adoption and ensure revenue predictability.

It's important to release your pricing early to confront the market and gather feedback from paying customers, rather than being overwhelmed by opinions from those who won't pay.

Expect your pricing strategy to evolve over time, typically every year or so, as you gather more data about your customers and market.

Incrementally raising prices until you receive pushback from users can help you find the ideal price point where customers complain but still pay.

If you're confident in your product, encourage customers to sign up for an annual contract with a 30 or 60-day money-back guarantee, making it a recurring revenue stream from the start.

Start with usage-based pricing for new customers, then transition them to a minimum monthly commitment with volume discounts based on their average usage.

Startups should experiment with pricing strategies, especially when they have a small customer base, as it's easier to adjust prices than to raise them later.

New features are a great way to upsell; I often offer a 30-day trial of a new feature and ask if users would be willing to double their price if they find it valuable.