Teachable Creator Checkout 2.0
Surpassed the existing checkout in a controlled A/B test, improving both conversion and speed.
TL;DR
Problem: Third-party checkout was off-brand, inflexible, and created friction at a critical conversion point
Solution: Designed and built a custom checkout experience to improve trust, speed, and scalability
Impact: Increased conversion from 44% → 56% (+12 pts) and reduced checkout time by 2x (16 min → 6.5 min)
Role: Led end-to-end design of a new checkout system, from concept through launch and experimentation
A custom checkout built to increase conversion
Creator Checkout 2.0 focused on improving conversion by redesigning Teachable’s checkout experience from the ground up.
I led the end-to-end design of a new checkout system focused on trust, speed, and scalability. The goal was to increase free-to-paid conversion and create a scalable foundation for future monetization.
Context
Teachable relied on a third-party checkout solution that limited flexibility and created a fragmented, off-brand experience.
This led to several issues:
- Lack of trust at a critical payment moment
- Limited customization and poor brand alignment
- Inability to collect detailed data or run meaningful experiments
- Poor mobile experience
Because checkout directly impacts revenue, improving this flow became a high-priority growth opportunity.
Constraint
The new checkout needed to replicate core functionality of the existing system while improving performance—working within existing payment infrastructure and APIs.
Role
I led end-to-end design of the checkout system, partnering closely with product and engineering to define scope and ship the system.
- Defined the structure and UX of a multi-step checkout flow
- Designed for trust, clarity, and speed at critical decision moments
- Collaborated with engineers to align on Stripe components and system constraints
- Iterated based on research, audits, and experiment results
Decisions
1. Build a custom checkout to unlock control and scalability
Moved away from a third-party UI to enable better UX, data visibility, and experimentation.
2. Prioritize trust and clarity at the point of payment
Introduced clear order summaries, improved microcopy, and consistent branding to increase confidence.
3. Reduce friction in form inputs
Implemented auto-fill, address suggestions, and simplified fields to reduce effort and errors.
4. Optimize for speed and decision-making
Simplified the flow, reduced unnecessary choices, and improved scanability to help users complete checkout faster.
5. Design for future growth
Built a flexible system that could support upsells, promotions, and experimentation over time.
Impact
Increased conversion and revenue through a redesigned checkout system
- Increased free-to-paid conversion from 44% → 56% (+12 pts)
- Increased projected new subscribers by 25% (+2,220/year)
- Reduced checkout completion time from 16 min → 6.5 min (2x faster)
- Validated performance through a 50/50 A/B experiment
The redesigned checkout not only matched but surpassed the previous system, demonstrating improved performance and user experience.
Insight
Checkout is highly sensitive to trust and detail—small UX improvements can have an outsized impact on conversion, especially when users are making financial decisions.