Moving Big Cartel’s primary acquisition motion to a free trial
I co-owned an 18-month effort with my PM to move Big Cartel’s freemium acquisition model to a reverse trial motion, where a seller has the opportunity to upgrade to a paid plan or downgrade to a free plan. After shipping multiple experiments, reverse trial had become the company’s primary acquisition motion.
| Role | Design lead |
| Team | Me, Lead PM, 3 Engineers |
| When | 2025-2026 |
| Result | Shipped 5 growth experiments that led to changing Big Cartel’s primary acquisition motion |
Over the course of this work,
- We formed hypotheses and planned experiments to test them
- I optimized the user experience across the entire funnel: sign up, checkout, billing, plan-locking, failed-payment behavior and offer logic.
- We synthesized the results and shared out broadly to the company
This case study will cover the major learnings and design decisions specifically that led us to making reverse trial our primary motion.
Reassure customers emotionally at critical times in their decision-making journey
Our first hypothesis was that removing friction from the checkout flow for free users upgrading would increase paid upgrades. I made the checkout a small modal to make it feel like you were moving through faster.
And… this was extremely unsuccessful. By removing friction, we also removed reassurance of a big decision moment. Reducing the number of clicks doesn't help someone who’s worried about being billed in seven days. Entering a card for a payment the first time is a bigger decision moment than charging your existing card more, so we need to make sellers feel reassured at this critical moment.
I propagated this learning in 2 practical ways:
- Kept checkout page full page, and added moments of reassurance to the seller
- Killed any mentions of the trial once they’ve paid us. The seller experience needed to match their mental model state as confirmation they’ve made the right choice.
Asking for a credit card at the end of the trial only works if the seller comes back
For a platform like ours, daily active usage is not a metric we track because it doesn’t necessarily map to seller success. Crafting your brand and setting up your store, especially if this is maybe your side hustle, doesn’t happen every day. Maybe you do a lot over the weekend, and finish a few days later. This played out in our initial test. When we asked for payment at the end of a 7-day trial, we saw a huge 20% upgrade rate. However, only 5% of our original sign-up cohort showed up on day 7.
While a credit card upfront trial feels bad, it proved to work for our type of seller and steered us more effectively: increase trial starts.
Through trial and error, we got to the win
Big Cartel changed its primary way of how it acquires customers on the back of this work.
Our target was to get over 50% of trial starts to start a paid subscription. By the end of the experiments, we saw 56% of trial starts start a paid subscription.