Alex Goldwyn is the founder of BillingHub (billinghub.online), invoicing software for freelancers and small businesses that charges per invoice instead of a monthly subscription. The idea came from noticing that most invoicing plans are priced for heavy senders, while many freelancers and small shops send only a handful of invoices a month and keep paying for capacity they never use. BillingHub launched in July 2026 and is bootstrapped. Clients can pay BillingHub invoices by card through the seller’s own Stripe account, and BillingHub takes no cut of the payment. Alex builds and runs the product and writes about getting paid on time, invoice basics, tax lines on invoices, and what invoicing tools really cost a business that sends a few invoices a month.
Company: BillingHub
We are thrilled to have you join us today, welcome to ValiantCEO Magazine’s exclusive interview! Let’s start off with a little introduction. Tell our readers a bit about yourself and your company.
Alex Goldwyn: I’m Alex Goldwyn, founder of BillingHub (billinghub.online). BillingHub is invoicing software for freelancers and small businesses, and it charges per invoice instead of a monthly fee. You create an invoice, estimate or quote, send it by email, and if you connect your own Stripe account your client can pay it by card from a button in that email. We take no cut of that payment. We launched in July 2026, we are bootstrapped, and the product is built for people who send a handful of invoices a month rather than hundreds.
What was the moment you realized that complexity was holding your company back, and how did that shift your approach to product, operations, or strategy?
Alex Goldwyn: It came before we launched, when I read the pricing pages of 22 paid invoicing plans side by side. Every one had tiers, caps on invoices or clients, a monthly and yearly toggle, and add-ons. Laid out together, the median plan only beats $1 per invoice once you send 38 invoices a month, and most of the people we were building for send far fewer. That changed the plan. Instead of designing one more tier table, we decided the price should be the simplest part of the product: you pay for an invoice when you issue it, and nothing else.
Can you share one specific example of something you simplified (a product feature, process, pricing model, or customer experience) that delivered outsized results?
Alex Goldwyn: Pricing is the clearest one. It is $1 an invoice on a 25-pack, and a credit is spent only when an invoice is actually issued. Drafts, estimates and quotes cost nothing. The result is a pricing page that fits in one sentence, and the question “which plan do I need?” mostly disappeared, because a small sender never needs to pick a tier. The second one was sign-up. Our onboarding used to be eight screens, and the first one asked for a date of birth that nothing in the product used. We removed it and added a “Skip for now” button once the required answers are in, so a new account gets to the product in a minute instead of a form.
How do you systematically identify and eliminate complexity across the organization without oversimplifying in ways that hurt quality or value?
Alex Goldwyn: For every field, step and setting we ask one question: what uses this? If nothing does, it goes. The date of birth on our sign-up was exactly that, a required field that nothing ever read. The other half is knowing what not to remove. Some friction protects the customer, and that stays. An issued invoice in BillingHub is locked and cannot be edited, and a mistake is fixed by issuing a new one. It is one more step for the seller, but it is what an accountant or a client expects from a document that says money is owed, so simplifying it away would make the product worse, not simpler.
What’s the biggest resistance you’ve faced when pushing for radical simplicity, and how did you overcome it?
Alex Goldwyn: Mostly the conventional wisdom that software has to be a monthly subscription. Per-invoice pricing is less predictable for us than recurring revenue, and some people who send a lot of invoices do prefer a fixed plan. We did not answer that by going back to tiers. We kept the pay-per-invoice packs as the default and added a single yearly plan for heavier senders. So there are two ways to pay, and a light user never has to read about the second one.
For other CEOs who struggle with feature bloat, process overload, or confusing customer journeys, what’s the most important principle or first step you would recommend they take?
Alex Goldwyn: Write your price, or your onboarding, as one sentence a customer could repeat to a friend. If you cannot, that is where the complexity lives. Then go through what you ask of people and remove anything that nothing in your product actually uses. It is a small first step, but it is the kind that shows you how much was there only because nobody asked why.
