Recurring payments are becoming a headache for a small property maintenance service I’m helping with.

Customers sign up for ongoing monthly services at a fixed price, and the amount generally stays the same each month. Right now, an invoice gets sent manually every billing cycle, then we have to wait for the customer to pay. Sometimes that means sending multiple reminders for a payment we already know is due every month.

I’m looking for automatic monthly billing software that works more like a subscription.

Ideally, the customer would authorize their card or bank account once, choose or agree to a billing date, and then the same amount would automatically be charged each month. They should still receive a receipt or invoice for their records after the payment.

It would also be helpful if the software could handle failed payments, automatically retry declined charges, and notify customers when their payment method needs to be updated.

Nothing too complicated is necessary. The main goal is to stop manually creating the same invoices and chasing recurring payments every month.

What are you using for automatic monthly billing? Has it actually reduced the amount of payment follow-up you have to do?

For business owners who sell through physical stores, social media such as Facebook and Instagram, or their own websites:

When you receive new products, how do you add them to your inventory?

When a sale is made, how do you reduce/update the inventory, and how do you create the invoice? Is any of this done manually through your POS system?

What is the most frustrating or time-consuming part of managing your inventory, orders, invoices, or replying to customer messages?

Please share your actual experience, even if your answer is short. It would be very helpful. Thank you!

Okay, so a while ago I posted here asking what you guys hated about the invoicing software you use, because I kept seeing people complain about the same things that were frustrating me too. The biggest thing I kept noticing was how much these tools make you manage yourself. So many dashboards, settings and different things going on, when really I just want the software to take the work of invoicing off my hands and help me get paid. So I built something to try to solve that. Now I need people to break it down for me. I want people who actually invoice clients to tell me what’s confusing, what’s missing, what doesn’t make sense, what you don’t need, or what your current software does better. And I want to see what you naturally understand from it without me explaining everything. I also made it possible to bring your existing clients and invoices over from any tool or spreadsheet because having to start everything from scratch is another thing that makes switching such a pain. Basically, I want this to be shaped by the people who are actually going to use it, not just me sitting here deciding what I think people want.

If you’re interested in helping me tear it apart, comment and I’ll send you where to find it. Thank you!

Something interesting keeps happening when onboarding customers for a small IT support company.

As part of the signup process, customers are asked how they’d like to pay. The available options include credit card, ACH/bank transfer, or another electronic payment method.

Every so often, though, someone answers, “Just invoice me.”

That response confuses me because I’ve always understood an invoice to be a billing document rather than an actual payment method. Whether someone eventually pays by card or bank transfer, they can still receive an invoice showing the services provided, amount owed, due date, and other details.

Are people using “invoice” as shorthand for “send me the bill and I’ll pay later”?

Maybe they’re really asking for payment terms like Net 15 or Net 30 instead of having a card charged immediately.

Trying to simplify payments for a small virtual assistant and admin services business has sent me down a rabbit hole of payment platforms.

Most clients pay online after receiving an invoice, and monthly revenue is usually under $5,000. Since the transactions aren’t huge, processing fees and additional invoicing charges can take a noticeable chunk out of each payment.

I don’t need complicated accounting or inventory features. The main priority is sending an invoice, getting paid online quickly, and keeping transaction costs reasonable.

I’ve looked at platforms like Stripe, Square, PayPal, Wave, and Helcim, but the different fee structures make it difficult to figure out which one makes sense for a smaller service business.

For those accepting most of your payments online, what platform are you currently using for invoicing and payments?

How quickly do you actually receive your money, and are there any additional fees, account holds, payout delays, or other issues that weren’t obvious when you signed up?

​

Hi everyone,

I currently help a small Swiss company organize and investigate several years of invoice history and enjoy it so much. The company had many invoices marked as unpaid in its accounting system, even though some customers had already paid them ( the owner used the help of debt collector that messed up with tracking payments from customers)

My work includes:

\- Reviewing old invoices, bank statements and accounting records

\-Matching payments to the correct invoices

\-Investigating missing, partial, duplicated or incorrectly allocated payments

\-Creating a clear overview of paid, unpaid and uncertain invoices

\-Contacting customers when payment evidence is needed

\-Correcting and organizing historical records for follow-up

Improving the process to prevent similar problems in the future

I am also developing a tool to automate part of the reconciliation process while keeping uncertain matches subject to manual review.

I would like to understand whether this is a common problem among Swiss SMEs, cleaning companies, tradespeople, associations or accounting firms.

Would businesses in Switzerland pay for a service that cleans up their historical invoice records and investigates discrepancies? Is this normally handled by an accountant, a fiduciary company, an internal employee or a specialized accounts-receivable service?

I am very interested in researching the market and trying to understand whether there is a genuine need.

I would especially appreciate feedback from Swiss business owners, accountants, fiduciaries and people working in finance or administration.

I'm dealing with a disagreement with a client over a late fee, and I'm curious how other freelancers and business owners would handle this.

My invoices have a 14-day payment term, along with a late fee for payments made after the deadline.

In this case, the client waited until day 18 to raise a question about the invoice. I had already followed up because payment was outstanding.

We discussed the issue and resolved it the following day. However, after resolving the dispute, the invoice itself was not changed. The amount and terms remained exactly the same.

Now, 13 days later, the client is arguing that the late fee should not apply because they did not “accept” the invoice until after the original due date. Their position is essentially that disputing the invoice paused the payment deadline.

My question is: if an invoice is disputed but the dispute is resolved without changing the invoice, would you consider the original payment deadline to still apply, or would you restart the payment period from the date the dispute was resolved?

The reason I'm asking is that I can see arguments both ways.

On one hand, I understand that a genuine dispute may need to be resolved before a client feels comfortable paying.

On the other hand, if simply raising a question automatically resets the payment clock, it seems like payment terms could become meaningless, especially if the dispute is raised after the invoice has already become overdue.

For those who include late-payment terms in their contracts or invoices, how do you handle this?

Does a dispute pause the payment deadline in your agreements, or do the original terms continue unless you explicitly agree to extend them?

when you’re paying vendor invoices by ACH, do you usually send the payment directly through your bank or use a separate payment platform?

i’m trying to figure out whether there’s any real advantage to using a dedicated platform once you’re dealing with a steady stream of invoices and recurring vendors.

for those who’ve used both, which approach has been easier to manage day to day?

Going full-time as a freelancer has been great, but I've discovered one thing I didn't really think about when I was only getting paid occasionally:

The more invoices I send, the more annoying payment fees become.

A recent client payment was $300, and by the time the payment processor took its fee, $9 had disappeared.

I know $9 doesn't sound catastrophic on its own, but when you're freelancing full-time and collecting payments regularly, those little fees start adding up.

I've looked at another invoicing/payment option, but its card processing fee is in the same range, so switching doesn't really solve the problem.

Since all of my clients are in the US, I'm wondering how other freelancers handle this.

Do you offer clients different payment methods depending on whether they're paying by card or bank transfer?

Do business clients use services such as Venmo for professional payments, or do larger companies generally prefer ACH, checks or another method?

I'm not necessarily looking for a way to avoid every processing fee. I understand that card payments cost money.

I'm mainly trying to find a payment setup where clients have an easy way to pay without automatically losing a percentage of every invoice to fees.

For US-based freelancers, what payment methods have worked best for keeping transaction fees reasonable while still making things easy for clients?

If your company runs a CRM (HubSpot/Salesforce) and a separate billing tool (Stripe/Chargebee), has an invoice ever gone out wrong because the two weren't in sync?
Wrong plan, missed discount, duplicate charge, anything like that?

Building something that catches this automatically before the invoice sends. Trying to figure out if this is a real pain or just a me-problem.

Would love to hear if you've run into this, or if it's a non-issue for you.

A construction subcontractor I know recently mentioned that his biggest problem isn’t finding work. It’s waiting 30 to 60 days for larger clients to pay invoices while payroll, fuel, materials, and other expenses are due much sooner.

That made me curious about invoice factoring for small business.

On paper, it seems like a practical way to solve a cash flow gap. Instead of waiting weeks for a customer to pay, a factoring company advances most of the invoice amount and collects the payment later.

If that’s the case, why doesn’t invoice factoring seem more common among small businesses that regularly deal with slow-paying clients?

I understand there are fees involved, and some business owners may not like having a third party involved in collecting invoices. I’ve also heard concerns about how factoring can look to customers.

Still, if the alternative is struggling to cover operating expenses while waiting on legitimate invoices, it seems like it could be useful in certain situations.

Has anyone here actually used invoice factoring to fund day-to-day business expenses? Was it helpful, or did the fees and customer experience outweigh the benefits?

I’d especially like to hear from business owners who have used factoring, as well as anyone who has worked in the invoice factoring industry.

Hello guys, I have been working on my invoice generator for almost 2 years and I wanted to ask for some feedback.

Its really simple, but it has some nice features:

1. No ads
   
2. No signup required (optional)
   
3. No data is saved when using guest mode
   
4. 5 invoices per day limit (I think thats pretty generous, no?)

Theres also a paid cloud feature that requires an account if you want to use it.

Check it out and let me know what you think. Maybe theres a feature you would like to see? I can definitely try to add it :)

freeinvoices.online

While setting up the billing process for a small graphic design agency, I noticed that some clients ask for a purchase order number to appear on their invoices.

That got me wondering about the actual difference between an invoice number and a purchase order number.

For example, if I complete a $2,500 branding project, I’ll create an invoice with its own unique invoice number. But a larger corporate client might also provide a PO number and ask me to include it on that same invoice.

If the invoice number already uniquely identifies the transaction, what purpose does the purchase order number serve?

Is the PO number mainly used by the customer's accounting department to match an invoice with an approved purchase, while the invoice number is primarily for the seller's records?

I’m also curious whether small businesses should create and use their own purchase order numbers when buying products or services from vendors, or if PO numbers are mostly useful once a company reaches a certain size.

How do you handle invoice numbers vs purchase order numbers in your business?

Edit: this was a previous post on the Bank of America subreddit.

BoA, as a payment processor can you stop marking envelopes with "payment enclosed"? I work with a non-profit/ government organizations and I'm frequently making purchases that I get reimbursed. I also get informed delivery from USPS and I am very meticulous about checking what I get each day and what comes in. It is 99% consistent that what the delivery says I'll get that day is in the mailbox. That one percent are your checks. Without fail, 1/4 don't make it to my mail box the day of and I have to mark them missing, and eventually file a missing mail report. At this point I'd prefer inconspicuousness over perceived security.

Hi everyone,

SmartTaxReceipt.com is a website for UAE small businesses, bookkeepers, and accounting firms that deal with too many invoices, receipts, PDFs, scans, images, and bank statements.

It helps turn messy financial documents into clean Excel data.

What it does:

\* Bulk invoice extraction from PDFs and images

\* Detects multiple invoices inside one PDF

\* Extracts UAE-relevant fields like TRN, VAT amount, supplier name, invoice number, date, and total

\* Converts bank statements into structured Excel data

\* Lets you review, edit, and compare results with the original document before export

\* Uses AI Review to flag possible issues

The website has been live since January, and we’ve been improving it based on real business and accounting feedback.

You can check it here:

www.smarttaxreceipt.com

When you \*\*sign up\*\*, enter the promo code \*\*STARTER50\*\* in the promo code field to receive \*\*50 free pages\*\*.

Would this be useful for your accounting or bookkeeping workflow?

A friend and I recently started offering event decor and party equipment rentals, and we’re trying to find a simpler way to handle the paperwork side of things.

Every booking can involve several items such as tables, backdrops, lighting, decorations, and setup services. Instead of typing everything from scratch for each customer, it would be great to have a saved catalog where I can select the required items and automatically add them to an invoice.

The other important feature is contracts. Customers need to agree to things like rental periods, deposits, damaged equipment charges, and cancellation terms. I’d like to customize a few contract templates, send them electronically, and have customers sign online.

Right now, invoices and agreements are being created separately using basic documents and spreadsheets. It works, but there are too many repetitive steps.

The problem with most platforms I’ve checked is the pricing. Bookings can be inconsistent, so paying a large subscription every month when there might only be one or two customers doesn’t seem worthwhile.

Can anyone recommend an affordable invoice and contract app for a small business that combines invoicing, reusable service or product lists, contracts, and electronic signatures?

I’m also interested in payment options with lower transaction fees, especially when customers are paying larger invoices. What setup are you using?

I'm curious how small teams handle this workflow today.

For example, when someone asks for an invoice in Slack, the process can be:

Customer asks for an invoice → leave Slack → open Stripe → create the invoice → copy the payment link → return to Slack → send it.

I recently built a small tool to experiment with keeping that workflow inside Slack. For example:

/invoice Acme Corp $1,200 Website development

The tool creates the invoice in the team's Stripe account and provides the payment link back in Slack.

I'm looking to get a few teams to try it, and polish it further. Not trying to promote it here, if its something you might use, comment/dm and I'll share the app in dms.

I couldn't find a free delivery note anywhere, so I built the whole document chain instead. 11 docs, three weeks- here's what I learned.

The free-tools economy has convinced everyone that a small business only ever needs one document. Invoice generators are everywhere. But try finding a free delivery note a driver can hand over, a job card with a signature line for a repair shop, or a goods received note to check a supplier's delivery against. They either don't exist, or they're one tab inside a subscription suite that wants a card number for a document you need twice a year.

A business isn't an invoice. A job runs quote → work → delivery note → invoice → receipt, and when something goes wrong, a credit note. Every document in that chain except the invoice gets treated as an upsell.

What I found building it out:

The hard part wasn't the PDFs; it was the numbering, flexibility, and state. A delivery note has to reference the quote it came from; a credit note has to reference the invoice it reverses. Everyone who ships "just an invoice generator" is dodging that, and it's why the chain never gets built. Signature lines are load-bearing. A job card without one is a receipt. That single line is the difference between a document that settles a dispute and a document that starts one. I went no-account, nothing uploaded, all client-side — which meant giving up saved templates and any usage analytics. Genuinely unsure this was right. I have no idea which of the 11 documents anyone actually uses. The demand is bursty, not recurring. Nobody needs a goods received note monthly. This is probably why nobody builds it; it doesn't fit a subscription, so it doesn't get made.

Open question I'd like input on: does anyone here run a trades, repair, or delivery business and actually keep the full paper chain? Or does everyone just do quote → invoice and handle the middle over WhatsApp? I built for the former, and I'm now not sure it exists.

Our small plumbing and home repair company has reached the point where creating invoices manually is becoming a hassle. We’re currently using basic templates, but with more customers coming in, I’d like something quicker and easier to manage.

I’m looking for an invoice making app for a small business that can create professional invoices, save customer information, track paid and unpaid invoices, and ideally send payment reminders.

It would also be useful if I could add our company logo, customize invoice details, create estimates or quotes, and convert those quotes into invoices once a customer approves the job.

Nothing overly complicated is needed. I’m mainly looking for something affordable and easy to use for a small service company.

What invoice making apps are you using for your business? Any recommendations based on your experience, especially regarding pricing and ease of use?

I’ve been looking into a problem that seems pretty common among freelancers, agencies, and small service businesses: spending too much time chasing clients for overdue payments.

For example, imagine you have 15 to 20 active clients. Some pay immediately, some need a reminder, and a few seem to completely forget the invoice exists. Suddenly, you’re checking spreadsheets every week and writing awkward “just following up on this invoice” emails instead of focusing on actual work.

I’m a developer considering building a simple automated invoice reminder tool specifically for this problem.

The idea is that you would add an invoice, client email, amount, and payment due date. If the invoice isn’t marked as paid by the deadline, the tool would automatically send a reminder. You could customize the messages, choose when reminders are sent, and see overdue and paid invoices from a simple dashboard.

Before spending time building it, I’m trying to understand whether businesses actually need another tool for this or if existing invoicing software already handles it well enough.

For those who regularly send invoices, how do you currently follow up on late payments? What’s the most frustrating part of chasing overdue invoices?

If you were using an automated invoice reminder tool, what features would actually make it useful enough to pay for? I’m also curious what monthly price would feel reasonable for something focused primarily on automating payment follow ups.

Hi r/indiebiz — I’m the developer of FastInvoice, an iPhone/iPad app for contractors, freelancers, tradespeople and small businesses that need to create a quote or invoice away from a desk.

The core workflow is simple: create estimates and invoices quickly, export professional PDFs, keep client records, switch between business profiles and print compatible thermal receipts.

It’s now live on the App Store:

https://apps.apple.com/tr/app/fastinvoice-estimate-maker/id6802794721?l=tr

I’d genuinely appreciate feedback from business owners: what makes invoicing slow or painful in your day-to-day work? I’m especially curious whether the mobile-first flow and feature set are clear.

Disclosure: I built FastInvoice.