Everyday and professional decision
Raise the price for everyone, for new customers only, or add a tier?
Three models said raise it for new customers only. Grok said leave it and add a higher tier.
The question
We sell a $29 per month productivity app to freelancers. We have about 3,000 subscribers and monthly churn is around 4 percent. We are considering raising the price to $39. Should we raise it for new customers only, raise it for everyone with notice, or leave the price alone and add a higher tier instead?
The answer that came back
Raise the price to $39 for new customers only, and grandfather your existing 3,000 subscribers for now. A 34% increase is large enough that you should measure the drop in new-signup conversion first. Break-even is roughly a 26% drop in conversion, so if conversion falls less than that, you come out ahead on new revenue. Revisit moving existing subscribers (with 60+ days' notice) once you have 2-3 months of data, and consider adding a higher tier later as an upsell rather than a replacement. This is based on the figures you gave; I have no current market data on freelancer price sensitivity or competitor pricing, so let your own conversion data override this if it contradicts the assumption that demand is reasonably inelastic.
Agreement. Majority. Three of the four models chose the same option.
What each model said
Each answer is the model’s own words, with formatting marks removed.
Claude Sonnet 5.5
Raise for new customers only, now, and grandfather existing subscribers for 6–12 months before moving them with 60 days' notice. Reasoning: $29→$39 is a 34% jump, so testing on new signups is cheap and low-risk; 4% churn is healthy, and you don't want to jeopardize 3,000 loyal payers. If new-customer conversion falls less than ~25%, revenue wins. Then add a higher tier later as an upsell, not a substitute. Key assumption: freelancers' willingness to pay is price-insensitive enough; verify via conversion data.
GPT-4.1
Raise the price to $39 for new customers only. This captures additional value from incoming users without risking increased churn or dissatisfaction among your loyal base, whose retention is critical given the relatively high churn rate. Later, consider a higher tier with premium features to further segment revenue.
Gemini 3.5 Flash-Lite
Raise the price for new customers only. Key Reasoning: Grandfathering existing users preserves your core revenue base and rewards loyalty, protecting your 4% churn. Freelancers are price-sensitive; raising rates risks a mass exodus that outweighs ARPU gains. Simultaneously, testing $39 on new sign-ups validates pricing power. Load-bearing assumptions: Your 3,000 users are largely price-sensitive freelancers, acquisition channels can absorb a potential conversion dip at $39, and your current LTV easily outpaces CAC.
Grok 4.20
Add a higher tier at $39 instead. Your 4% monthly churn (~39% annualized) already signals retention problems; a price hike on existing users will likely accelerate cancellations and refunds. A new higher tier lets current customers stay at $29 while capturing more from power users who will upgrade, tests real willingness to pay, and avoids the long-term resentment of grandfathered pricing. Assumption: you can add clear, meaningful feature differentiation.
Where they differed
Claude, GPT-4.1 and Gemini chose to raise the price for new customers only. Grok preferred leaving the base price alone and adding a higher tier, worried that a rise would speed up cancellations given the churn. The final answer tells you to let your own conversion data override it.
About this run
Run on 26 October 2026 in quick mode with four models (Claude Sonnet 5.5, GPT-4.1, Gemini 3.5 Flash-Lite and Grok 4.20), one round, no cross-critique. Web search was off.
Pilot’s summary is advisory input, not a decision. Models can be wrong together, and agreement is not proof. This is an example, not advice for your situation.
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