Quick note: This is a brand new recipe to complement my Prompt Hackers Cookbook - a collection of 220+ copy-paste ready AI prompts organized by what you’re trying to accomplish.
Note that the ‘Combine with’ suggestions reference recipes in The Prompt Hackers Cookbook
The Problem
You’re leaving money on the table with existing customers, but can’t identify where the natural upgrade paths exist.
The Outcome
A prioritized list of 5-10 specific upsell opportunities with implementation difficulty, revenue potential, and customer readiness scores for each.
Time Required: 30 minutes
Difficulty Level: Advanced
Best Platform: Claude (better at strategic analysis and pattern recognition)
What You’ll Get
A strategic roadmap of 5-10 specific upsell opportunities ranked by priority. About 60-70% will be genuinely viable options you could implement. 20-30% will require more research or validation. 10-20% might not fit your business model, but will spark ideas for what could work. The prioritization framework gives you clear next steps rather than an overwhelming list of possibilities.
Variations
Quick Version: Remove the detailed scoring system and just ask: “Give me the top 3 upsell opportunities I’m missing based on [customer data]”
Deep Version: Add: “For each opportunity, create a launch plan including positioning, pricing structure, and first 30 days of rollout”
Combine With
Recipe #11.7 (The Pricing Justification) to determine how to price your upsells
Recipe #11.8 (The Case Study Creator) to build proof for new offerings
Recipe #17.2 (The Quarterly Plan) to sequence your upsell rollout over time
Recipe #4.5 (The Risk Assessor) to evaluate risks before committing resources
Chef’s Tips
The best upsell opportunities already exist in your support tickets and customer questions. You don’t need to invent new problems to solve
If fewer than 20% of your customers could potentially buy the upsell, it’s probably too narrow. Look for opportunities that serve broader segments
“Done-for-you” versions of your existing offering are almost always viable upsells (people will pay to not have to do the work themselves)
Upsells that solve problems your product creates or reveals are the easiest to sell (example: if you teach people to podcast, selling them audio editing is natural)
The implementation difficulty score matters more than revenue potential. A $10K opportunity you can’t deliver well is worth $0
Don’t confuse “customers are asking for it” with “customers will pay for it.” Validate willingness to pay before building
If an upsell requires you to become good at something you’re not currently good at, that’s not an upsell opportunity, it’s a pivot
Success Metric: If you can identify at least 2 "Quick Win" opportunities that you could launch within 30 days and have 10+ customers who'd likely buy them, the recipe worked. If everything scores high on difficulty or low on readiness, your inputs weren't specific enough or you're trying to force upsells that don't naturally exist.