10 reasons why companies move from Stripe Billing to Sequence

In preparation for a recent board meeting, we discovered that >50% of our revenue comes from Stripe Billing migrations.

We previously wrote about Why Stripe is Great and our admiration continues to grow, particularly in light of their Annual Letter, which pointed out that Stripe Billing is doing $500m in annual revenue run rate.

Sequence has been completing a record number of Stripe migrations in 2025, primarily for the reasons listed in our previous article, all of which can be summarized as follows: Stripe is a top class payment gateway and basic subscription management tool, but is not built for enterprise / sales-led contracts where pricing is custom.

Let’s take a step back to remember why so many teams start billing with Stripe in the first place. For early stage companies, Stripe is an easy way to begin collecting revenue using simple subscriptions and invoices, making it a perfect fit for PLG models where speed to onboard is key. Their API suite has established a strong reputation amongst the developer community, who see Stripe as one of the most flexible tools to embed within the revenue stack.

Yet more and more B2B teams are making the switch away from Stripe as they reach 5-10m+ in ARR. We surveyed dozens of prospects and customers to gather the reasons why:

1. “No customisation with regard to ARR/MRR calculations. We have slight iterations in their reporting processes, and don’t want to rely on a complex SQL query to adjust their data export from Stripe.”
2. “Inability to handle backdated billing schedules means that historical invoices can’t be easily generated, resulting in revenue leakage as some legacy invoices from older contracts fail to be issued in a timely manner.”
3. “Cost. As revenue scales, the 0.7% Stripe invoicing fee begins to feel disproportionate for a lightweight subscription management solution.”
4. “Simple but impactful UX details, like starting a billing schedule before the day it goes live or archiving erroneously created schedules make a huge difference to the user experience. Similarly, adding labels to contract phases helps to make complex deals easy to understand and manage.”
5. “For seat based products, we could not easily manage prorated overages for seat upgrades. Since moving to Sequence we have unlocked an additional $200k in revenue per quarter by tracking prorated overages”
6. “Instead of navigating endless back-and-forth support tickets, we like that Sequence works directly with us during the onboarding and the ongoing support team quickly fixes errors and takes in feature requests with urgency. For teams that are scaling fast, this kind of collaboration is essential.”
7. “Having to rely on developers to enact changes via API due to an incomplete dashboard experience. No finance operator wants to be held up on billing run week by a pending engineering ticket.”
8. “Enterprise involves a lot of custom pricing involving different structures. This is possible to do in Stripe, but a huge pain point as we have to create a new pricing model each time without an easy way to expand our product catalog with more complex models.”
9. “We have a quarterly true-up model where we bill conditionally if there are additional seats for the Enterprise plans. These are all manual changes within Stripe right now and with a growing customer base this becomes a significant time commitment.”
10. “Our order form process is completely detached from Stripe invoicing, so mistakes can occur if things do not match and it also creates duplicative work.”

At Sequence, we continue to see teams reach the turning point with Stripe. Even those who previously accepted Stripe’s limitations make the switch when they realize how much time, revenue, and flexibility they’re sacrificing by sticking with a billing tool that wasn’t built for their business model. As growth breeds increasing complexity in pricing, the need for a scalable, full-featured revenue collection system becomes impossible to ignore.

Sequence offers a path forward: a robust billing platform purpose built to handle complex sales-led, hybrid, and usage based pricing models that sales & finance teams actually enjoy using.

As we often say to our customers, “Use Stripe for payments, Sequence for billing”. Our native Stripe payments integration and managed migration service has made this a no-brainer for our customers, and we expect this trend to accelerate in the coming months.

Thanks to the teams at Incident.io, Workshop, and Arcade and several other Sequence customers for their input on this post.