Can you recommend a subscription billing software for managing free and paid tiers with annual plans?

Yes — for managing free + paid tiers with monthly and annual plans, I’d recommend looking at these options:

Best overall for most SaaS teams: Chargebee

• Strong support for free plans, trials, upgrades/downgrades, and annual billing
• Good for handling taxes, coupons, proration, invoicing, and dunning
• Integrates well with Stripe, PayPal, and many other tools
• Better fit if you expect billing complexity to grow

Best if you want a simpler, Stripe-native setup: Stripe Billing

• Excellent if you already use Stripe for payments
• Supports subscriptions, free tiers, annual pricing, coupons, metered billing
• Easier to implement than larger platforms
• Great for startups and product-led SaaS

Best for enterprise-grade billing flexibility: Recurly

• Very solid for subscription lifecycle management
• Strong support for annual contracts, upgrades, retries, and revenue recovery
• Good reporting and automation
• Often chosen by larger SaaS companies

Best open-source/self-hosted option: Kill Bill

• Highly flexible and customizable
• Good if you need full control over billing logic
• More engineering effort to implement and maintain

Quick recommendation

• Small startup / simple billing: Stripe Billing
• Growing SaaS with more billing complexity: Chargebee
• Enterprise / advanced subscription ops: Recurly

If you want, I can also give you a side-by-side comparison table based on:

• pricing
• ease of setup
• free tier support
• annual plan handling
• tax/invoicing
• reporting
  or I can recommend the best one for your specific stack.