How Tomorro scaled a new AI feature to €200K in just 2 months

🔍 TL;DR

• Company: Tomorro - AI-powered contract management for companies
• Challenge: Monetizing AI-powered assistant
• Solution: Introduced paid features and value-based upselling
• Impact: 26% conversion in 2 months and €200K in added revenue
• Takeaway: Strategic upselling and user education drive AI monetization

Context

Today, I’m breaking down Tomorro and how to successfully monetize an AI-powered assistant by introducing paid features and a strategic upselling approach, with key takeaways you can start applying tomorrow. Let’s dive in!

Product 101 for Executives

• Usage-based blocking: Block access when usage exceeds limits to drive upgrades
• Customer tiering: Segment customers by value to prioritize features and support
• Rotating AI squad: Dedicated AI team rotates regularly to speed up delivery

Disclaimer: The organizational choices and technical solutions shared in this newsletter aren’t meant to be copied and pasted as-is. Always keep your company’s context in mind before adopting something that works elsewhere! 😊

The Company

Tomorro is an AI-driven contract management solution designed to help professionals optimize their workflows, automate repetitive tasks, and enhance efficiency. Their mission is to make AI a seamless part of everyday work.

🥵 Their challenge : slow customer adoption

Tomorro faced the challenge of evolving its legacy Product strategy to seize the opportunities offered by LLMs. They had to quickly find Product/Market Fit on new AI feature.

😢 How the Problem Affected Tomorro’s Performance

• Low revenue from free-tier users
• High engagement but low conversion
• Unclear perceived value of premium features

💡 Their idea to solve the problem

To address this challenge, Tomorro decided to launch their AI-Assistant named “Oro” by:

• Developing a premium AI feature that clearly enhanced productivity
• Get as many existing customers as possible to pay for the new feature and validate market/fit.
• Set a 2-month deadline to launch the new feature.

🤷🏼‍♂️ Why would it work

By demonstrating clear value and gradually introducing paywalls, users recognized the benefit of upgrading, leading to increased conversions.

✅ Their decisions to make it work

🍾 The results

For a successful AI feature launch:

1. Frame your AI feature as a cheat code, not a tool.
   
   Users don’t want “an assistant,” they want unfair advantages. The best-performing messaging focuses on what users can now do that was previously impossible or painfully slow. Make it feel like they’re unlocking a superpower — not learning how to use a robot.

2. Don’t launch until the AI output feels 5x better than the manual alternative.
   
   Speed and automation aren’t enough. The bar has been raised: for users to adopt an AI feature, the output quality must be dramatically better than what they’d do on their own. MVP-level AI will flop. Especially if users need to fix its mistakes.

3. Price like a partner, not a vendor.
   
   Instead of billing per seat or API call, charge for value unlocked. The best AI companies anchor pricing on outcomes (e.g. deals closed, content created, time saved). Bonus: it makes AI feel like an investment, not a cost center.

My full interview with Tomorro’s CEO

Dive deeper into this topic with Antoine Fabre, cofounder & CEO of Tomorro, in my latest podcast episode (in 🇫🇷).

🎙️ 📺 Listen now: Youtube / Spotify & Apple Podcasts

Tomorro just closed a $27M round and they're hiring!