Do you struggle with sending out invoices or estimates to your customers each week or month? Make this the year you get your invoices online and done with less hassle by using Web-based technology.
UPDATED AS OF MAY 2011: We’ve now updated this post 17 months after the original publication date. We’ve added more solutions based on reader suggestions. And we’ve updated the original information to reflect changes in pricing.
Here are 50 small business online invoicing software applications to help you manage sending your customer bills out — and do it with less labor and at a reasonable cost. In some apps, I state “approximately” because I’m converting the rates into U.S. currency and thus the monthly fee might fluctuate slightly. There are 21 new additions and one removed from the original 30 (it went out of business).
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AcceptPay  is a new electronic invoicing service from American Express. The full version AcceptPay is $30/month and integrates with QuickBooks, accepts online payments, ACH, and eChecks. I was impressed to see American Express entering this marketplace and putting some of their muscle into an online invoicing and billing solution. (Note: American Express is a sponsor of this site.)
Ballpark  is an online invoicing service that believes the key component of any customer relationship revolves around communication. So, their dashboard tracks the back and forth dialogue between you, your customer, and your team. They offer a free personal plan and the small biz plans start at $6/month.
BambooInvoice  is a free open source invoicing software for small business and independent contractor types. You load it on your own servers; it is not hosted like most of the others listed here. It offers a good online support forum as well. This is the only open source application I’ve seen in this space and it is one to watch for that reason.
BillingBoss  is a completely free online invoicing tool aimed at both freelancers and small business. It is owned and sponsored by Sage Software (owner of SageCRM, Peachtree and many other apps) and is both an outreach by them to serve the small biz owner and a very soft plug for their other products (which doesn’t diminish its functionality and value, in my book). A really cool thing is you can use your existing merchant account with their Payment Plus option for $5/month. Again, the main invoicing tool is free.
BillingOrchard  offers a highly recommended Auto-Invoicing feature that customers often talk about, so their solution is ideal for those with recurring billing needs. They offer a 15-day free trial and then a lite version at $9.95/month and $14.95 for standard. When you use the auto-invoice features, there is an additional cost per month, by number of transactions.
Blinksale  targets small businesses and creative professionals who want to send well-formatted invoices easily. They have one simple plan at $15/mo. It offers a free 15-day trial and integrates with Basecamp (the well known project management service).
CannyBill  is a web-based billing and invoicing solution aimed at web designers or professionals, although it certainly has the features that most small business owners will want. It offers a fully functional free account with up to 10 invoices per month, then small biz plans start at $7/mo. Pricing ranges up to $29/month for the enterprise level. 30-day free trial.
Cashboard  is a free financial time tracking service that lets you invoice, send estimates and accept payments online. They were quick to create desktop widgets for Mac and Windows as well as the iPhone so that you are not tied to a browser to manage your information. I found their pricing options just a bit confusing because most of the others listed here offer unlimited usage when you buy the paid version. With their “Dynamic” $10/month plan, you pay a bit extra for usage by employee and invoices. They offer a free for life plan, too.
CurdBee  is online billing software for small business and freelancers. It offers a robust free level with unlimited invoicing and customers. It allows you to accept Paypal and Google Checkout, too. However, the free level invoices include a Curdbee logo, which seems fairly low key. Curdbee Premium level is only $5 a month and lets you remove the Curdbee logo from emails and invoices. The development team clearly thought about the customer with a demo that lets you take an in-depth look at the online invoicing service without even a trial. I give them a thumbs up for making it painless to learn more and for keeping it fast to make a decision.
Endeve  positions itself as an invoice management service. It offers a forever free plan with an unlimited number of invoices and customers. The Professional Plan is $20/month and allows you to create Pay Now buttons with Paypal, customize your invoice layouts, and manage your expenses.
Enliven Software  is for the larger small businesses out there. It is integrated with Microsoft Dynamics GP, Peachtree, and QuickBooks and automates accounts receivable and accounts payable processes for vendors and for customers. There was no pricing information available.
Freelance Total  is now called Billing Click. Online invoicing meets project management with this app (it is an additional cost to add the PM module to the invoicing module). Their web-based software allows you to take a client-centric approach to invoices as you manage the project. Plans start at a limited forever free plan and then starts at $19/month.
Freshbooks  is considered by many to be the market leader in Web-based online invoicing. It offers the standard features you’d expect, plus time tracking and the ability to manage subcontractors who are also working on your project. They integrate with other accounting and project management systems such as QuickBooks and Basecamp. They offer a fully free plan (some limitations) then plans start at $19.95/month. I have personally used Freshbooks and have found their service was elegant and easy to use. They have thought (for a long time) about their customers’ needs. (2011 Note: I still use the product and still really like it.)
Invoice Journal  is completely free. It doesn’t offer any pricing info and suggests it will be free forever.
The Invoice Machine  is an elegant application. You can do all the standard online invoicing functions, but in the tour, I was impressed with the flexibility. You can add line items in your invoice manually or from the project time tracking tool with a few clicks. You can create an HTML email invoice or attach one as a PDF. They offer an always free plan; then paid plans start at $12/month.
InvoiceMore  is an online billing and invoicing solution for freelancers, entrepreneurs, and businesses. It offers multiple features so that you can create, download, store, backup, print, and email PDF invoices to clients. You can track overdue balances. They offer a free plan; then only $15/month for an unlimited plan.
InvoicePlace  is an easy online invoicing service. One of the things that caught my eye was the simple offer of showing a completed sample invoice, in what looks like a Microsoft Word document. The tour explains the many features well. Free plan, then starts at $12/month.
Invoicera  offers invoices, estimates, and client reporting that you can use to track by specific product or service. You can add team members to a client and track their invoicing as well. Free plans, up to $49/month.
Invoices Made Easy  offers an online invoicing service exclusively for small service-oriented trades. From landscapers to consultants, they offer the standard online invoicing options, but they also have an “EasyMail” service which will send your invoice via postal mail. Flat $9.95/month with 30-day free trial.
Invotrak  is both an online invoicing and timesheet tracker. They offer good reporting tools as well as iPhone and iPod Touch apps. They have a limited Free plan up to an Unlimited plan at $45/month. It integrates with Basecamp.
LiteAccounting offers a free plan, then starts at $10/month. The dashboard shows three boxes front and center to keep you focused: Products/Services, Customers, and Invoices. They have a nice demo which answers most questions so you can decide without all the signup hassles.
Nett30 provides an online service for small businesses and contractors who need to make invoicing quick and user friendly. You can view real-time account summaries at any time. Send invoices as PDF, e-mail or have clients access them online. They have forever free plan, then starts at $13/month.
PaySimple  is another market leader and focused on recurring online payments, including invoicing. The invoice product is called “Invoice Simply” and is runs $11/mo. They also offer online payments and they have a Merchant Account background, so their service is oriented at credit card payments, ACH, eChecks, and online payment forms. If you need the combination of merchant account and all the other pieces that you’ve read about here, they are worth a look.
Ronin  is simple online invoicing product for freelancers all the way up to larger small businesses. Clients can log in to get their invoices or you can email them. You can try it out free without any worries of a time limit, but the free version is branded as powered by Ronin. After Free, plans range from $15/month up to $48/month.
SantexQ  is a project management and time tracking tool that also lets you bill clients directly from the service. It offers web-based reporting, but also lets you export to Excel for customizing reports as you like. For a single user it is free, but limited, then only $9.95 per month for unlimited users.
Simplybill  offers a clean interface and design to make the online invoicing process easy. The dashboard offers three tabs: Invoices, Quotes, and Clients. They offer the ability to keep in contact with your customers via reminders and thank you notes. There is the always-free account option, then starts at $5/month up to $25/month for premium. They have received excellent reviews and are worth a look.
Simplifythis  is more than an online invoicing application. It starts with helping you book your appointments online and ties that data into the billing tool. It offers two services that start at $9/month: EasyBill and EasyBook. No credit card required for free 30 day trial. What I liked most about this service was that they have captured the attention of busy small biz owners who know something about technology or were not at all computer-savvy and still love the service. They have done of good job of making it useful for a range of skillsets and that’s not easy to do.
Simply Invoices  follows their own name in concept for explaining what they do; they keep it simple. You can wrap your head around how they do things with a five step screenshot tour they offer, on one page. They offer a completely free plan then start at $9/month.
Winkbill  offers a robust online invoicing app at the free level all the way up to their platinum plan for $39.95/month. You can put your own logo on invoices with the free plan, but you can’t send them as a PDF. Loads of eye-catching templates you can use, too.
21 New Additions from May 2011 Update:
Time59  is focused on the solo law practice and attorney. They offer a free 30-day trial and free mobile access (some services charge for this as an add-on fee). It has a $49.95/year flat rate.
Zencillo  offers an invoice and billing product called Factura, which serves the Spanish speaking business owner. I used Google Translate to learn about the product in English. It starts at $25/mo for the basic plan.
Bill.com  is both an online invoicing and collaborative workspace. It allows you to store documents there so your co-workers and accountant can see them. They offer a 30-day free trial and then plans start at $19.99/m0. I liked that you could pay vendors by check, ePayment (ACH) or Paypal with a single click.
Ofuz  is another hybrid — online invoicing meets project management. They even have an email and web form capability. Offers a generous free plan, then starts at $24/mo.
InvoiceDude  is unique among web-based apps in that they offer a self-hosted option for those who want it on their own servers. The on-demand option is 100% free. The self-hosted option starts at $75/one time fee.
myTooq  designed with the small business in mind. Plus, when many web-based apps are explaining how they can keep you out of spreadsheets, myTooq explains that it works best for those that can track their expenses in a spreadsheet and take their information to their accountant at year’s end.
LessAccounting  looks and feels like an app to power a large enterprise, but its aimed at small business. The plans are built for those who want to go solo to those who want a bookkeeper. Pricing starts at $30/mo.
Billing Manager  is an Intuit product, which says a lot. It is a completely free tool, web-based, and you can easily add merchant services to get paid by credit card. I presume it will integrate with Quickbooks, but couldn’t find it stated on the site.
ReceivePay  offers two products: Secure Invoicing lets you create payment-enabled invoices directly from QuickBooks® or Microsoft Word. The other product is a credit card payment software, so that people can pay you instantly from the invoice by credit card. No pricing information available without filling out a form.
Moobiz  is a suite of business products from CRM to project management to marketing. Of course, it has an invoicing app with a 30-day free trial and then lowest plan starts at approximately $25/mo. You can add other apps as needed.
CheddarGetter  gets points for a catchy, different name. They are aimed at the micro-payments and subscription type businesses. It would work well with other types, but if you have a recurring payment take a closer look. Has a free plan, then starts at $39/mo.
InniAccounts  is a full online acctg solution, with invoicing tools, but meant to be an end-to-end solution. You get software to use, but you also get an accountant services. Starts at $113/mo.
Send Invoice  stands out in my mind. I remember them because their home page has a large UK postal box image and states — not every customer wants a PDF invoice… So, they’ll print it for you and mail it. Offers a free account, then $15/mo, but mailing invoices you have to pay for on any account.
Paperfree Billing  impressed me with its fast sample. You enter your email and they send you a sample invoice. Plus, they promise they’ll just send the sample and no spam or drip marketing. Sweet. Offers a limited free plan, then plans start at approximately $15/mo.
Tools4Com  provides a simple invoicing tool with a limited free version. In the upper left portion of the screen, look for your language of choice from French, German or English.
Smenta  is a robust business application suite. It is meant for automating key business processes like Customer management, Product Management, Sales Quotes, Order Processing, Shipping, in addition to Invoicing. They offer a startup plan that is free, then plans start at $299. It wasn’t clear if it was monthly or a one time fee or annual.
Tradeshift  is an online invoicing service. The home page talks about the social business network and the video implies a disruptive service. Once inside the dashboard, it was easy to create an invoice. If you are an international business, it might be worth a closer look as they are targeting an international supply chain. It is 100% free.
iComptroller lets you create Sales Invoices, generate Customer Statements, record customer payments and monitor your sales activities. Plus, you can sign in with your Google account. No pricing info.
Snapbill  states it is an online invoicing and automated billing solution. Automated billing is for those with recurring payments It has been getting rave reviews from customers and the media. Offers a free account, then starts at $12/mo.
ContraAccounts  is an advertising supported online invoicing tool that is 100% free. Actually, it is more of a full accounting system.
Billable  is one of the most impressive and truly light solutions I’ve encountered in this space. It is a beta product. You come immediately to a blank, customizable invoice at their home page. No sign up, no pricing, just an invoice looking document that you tab through and enter your information. You can then save as a PDF or print it. If you were without your computer, and needed to present an invoice asap, this would be a helpful little service to remember.
There you have it — a fair number of online invoicing and billing tools to help you save time invoicing your clients and customers. I hope this reduces your search time to find that perfect solution and that if you’ve tried one of these that you’ll let me know in the comments.
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These are the online invoicing and billing apps priced for small businesses that we think you might want to check out. Please note: details about the small business online invoicing software apps are believed to be accurate as of the time of publication, but features and offerings may change over time. Always check the vendor’s website for up-to-date details.
Special thanks to Smartsheet for help in compiling this list for us with their Crowdsourcing  service. Let us know what you think. Which small business online invoicing solution do you use in your company?