Tomorro · AI product · Mid · 45 to 60 minutes

Where should Tomorro place its first AI bet?

Tomorro is a contract management software company that helps businesses create, review, approve, and manage contracts. Answer this product management case and get it graded line by line against a weighted rubric.

Product strategy
AI scoping
Monetization
Metrics
Trade off analysis

The situation

You are the PM for a product area at Tomorro. The CEO and VP Product ask you for a recommendation on whether Tomorro should make AI a top priority in the next planning cycle, and if so, where to start. Tomorro already supports important contract workflows, but adoption of newer product bets has been slower than hoped and more prospects now ask what the company will do with AI. Sales says AI is becoming part of competitive conversations, while Customer Success warns that broad copilots are easy to demo but often fail to become part of daily work for legal and procurement teams. Engineering can support one meaningful AI initiative this quarter, not a broad platform effort. Your challenge is to propose an AI direction that fits naturally into Tomorro's existing workflow, solves a real user problem, and can show business value early enough to guide future investment. Leadership wants a point of view on what problem to target first, what the first version should include, and how Tomorro should know within one quarter if the bet is working.

What to produce

A 1 to 2 page product strategy memo.

Your answer must

Identify the user segment and contract workflow problem you would target first, and explain why it is the best first AI opportunity for Tomorro.
Describe the proposed MVP, including the user trigger, the AI output, where human review happens, and what is explicitly out of scope.
Compare your recommendation against at least one credible alternative AI direction and explain the trade off.
Define how Tomorro would package or monetize the feature, and how you would test willingness to pay or sales impact early.
Specify success metrics for the first quarter, including at least one adoption metric, one workflow outcome metric, and one revenue or pipeline metric.

Constraints

Tomorro can fund only one AI initiative in the next quarter.
The solution must build on Tomorro's existing contract management product, not a separate standalone product.
The first release must keep a human in the loop for contract decisions and approvals.
Leadership wants evidence of commercial value within one quarter, not just curiosity or usage spikes.

Format

Use short sections with headings such as Problem, Recommendation, Alternatives, MVP, Metrics, and Risks.

How Tomorro actually played it

Covers how Tomorro, a contract management company facing slow customer adoption, evolved its legacy product strategy by launching a new AI feature that reached about 200 thousand euros of revenue in two months.

Update an aging product strategy around AI opportunities
Tie the AI feature to a clear workflow
Track revenue from the feature early

Built from How Tomorro scaled a new AI feature to €200K in just 2 months by Timothe Frin.