Paddle Billing
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The company
Tailwind is the CSS framework for designers and devs who don’t want to compromise on quality.
What started as a side-project back in 2017 has grown into one of the most respected brands in the web-building community.
By constraining typography, spacing, and color into a system of tokens, Tailwind enforces design consistency across entire products. Mockups built in tools like Figma or Sketch translate more directly into production code, reducing drift between design intent and implementation. Resources like Tailwind UI provide ready-made, designer-polished components that accelerate workflows and maintain brand fidelity.
A top product and global growth brought with it payment and compliance pain, here’s how the Tailwind team overcame these hurdles with Paddle.
The challenge
Tailwind founder and CEO, Adam Wathan is no stranger to the billing and payments landscape.
Having built integrations with payment service providers in the past, he wanted to take a different approach with Tailwind UI - using a Merchant of Record that could handle all elements of the business’ payments infrastructure.
Adam was hoping this model would offer relief from sales tax liabilities and reduce the admin burden of bookkeeping.
But after finding a provider and getting set up, there was still an underlying concern over its stance on sales tax and what would happen if they were audited by the Canadian Revenue Agency (CRA).
We always had an undercurrent of anxiety around sales tax. Gumroad handled some of it for us but didn’t really have a solid stance on who was ultimately liable.”
Adam Wathan, Founder & CEO
In 2020, Gumroad was impacted by changes to PayPal’s terms and requested that clients manage their payments through PayPal directly. This new requirement made Adam’s concerns about sales tax a reality and meant a lot more work to manage payments in-house. Adam explains:
I’d actively avoided making my own PayPal account, it’s not a service I enjoy working with and it would really complicate our bookkeeping because we’d have to manage every payment, rather than payouts. Also, using our own account makes us the merchant and definitely liable for sales tax.”
Adam Wathan, Founder & CEO
The solution
Tailwind Labs realized they had two choices:
- A piecemeal approach, stitching together payment service providers (like Stripe and PayPal) and other tools to manage subscriptions and taxes (and ultimately managing tax liability in-house).
- Or a unified platform committed to handling all aspects of payments infrastructure for its customers.
On the surface, the unified platforms appeared more expensive.
But digging a little deeper, Adam found that piecemeal providers had complex fee structures that included additional charges on top of the base fee for cross-border payments and foreign exchange.
With our cross-border payments, we were looking at around 3.5% fees with Stripe and 4.5% with PayPal. So, any savings would have been minimal.”
Adam Wathan, Founder & CEO
For Adam, it wasn’t worth the extra tax management and admin it would bring to the team.
You just ask yourself, is any saving worth the admin burden and opening yourself up to extra scrutiny from the tax agencies? Absolutely not.”
Adam Wathan, Founder & CEO
That’s when he contacted Paddle.
As a Merchant of Record and provider of payments infrastructure for SaaS, Paddle takes on all tax liability for the transactions to all end customers, absolving Tailwind Labs from any non-compliance.
The results
Full control, without the compliance headaches
Since migrating to Paddle, Adam has been able to relax, safe in the knowledge that he doesn’t need to worry about sales tax.
[With Paddle,] we don’t have to worry about new markets charging tax on software. We can accept more payment methods now, including wire transfer and Apple Pay. It’s great because our checkout is almost self upgrading. We’ll be able to use more payment methods as they become popular because Paddle will make them available for us.”
Adam Wathan, Founder & CEO
Checkout optimized, true to brand
Tailwind Labs was also one of the first sellers to utilize Paddle’s Branded Inline Checkout, creating an integrated experience, rather than the hosted redirect checkout they had before:
We have a lot more control over the checkout experience now. It’s on brand and cohesive with our website, which really increases customer trust in the experience.”
Adam Wathan, Founder & CEO
The future
With Paddle handling all tax compliance woes, as well as chargebacks, support issues and checkout optimization, Tailwind are able to focus on what truly matters: The product and the customer.
As the team continues to optimize growth across essential new regions like India, they can rest assured tax compliance and payments aren’t going to be an issue.
We couldn’t be happier with Paddle.”
Adam Wathan, Founder & CEO
