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11 Entrepreneurs Share Their Best Billing Automation Tips

Scott Gerber
Scott Gerber

You have too much on your plate as a first-time entrepreneur to worry about managing all the intricacies of the billing process. Luckily, there are already systems in place that you can take advantage of to make things easier.

To find out which ones were favored by founders who'd been there, I asked a group of young entrepreneurs from YEC for their best sales or billing automation tips.

1. Make Getting Paid Simple

"I can say without a doubt that there are ways in which you can set up in-person, mobile, online and phone payments from one platform so that your customers have no reason they cannot pay you and do so quickly! Get paid quickly and make it inexpensive to chase money down using an all-in-one credit card processing platform. is a great one!" – Darrah Brustein, Network Under 40 / Finance Whiz Kids

2. Outsource

"Hire an accountant or accounting firm. Attempting to do billing in-house is foolish because it’s a distraction. Starting a new business as afirst-time entrepreneur is difficult enough without adding additional layers of complexity. You’ll already be working long hours, so stay focused on building your business and momentum towards profit. Take things off your plate so you can focus on your core business." – Joshua Lee, StandOut Authority

Read: Billing Software 101

3. Set Up Automatic Syncronization With Your Accounting System

"If you're using something like Freshbooks or another invoicing application, make sure to carefully sync it up with your accounting platform. SaaS-based offerings like Xero have simple integrations with most of the specialty invoicing and billing systems, but those systems can quickly become a problem if your chart of accounts doesn't get updated regularly. Save yourself some time and set yourself up for success through automation from the start." – Brian Fritton, Patch of Land

4. Install a Pop-Up to Collect Email Addresses

"On average, about two percent of your traffic is going to convert into a sale. To better that conversion rate, focus on collecting an email address by installing a pop up and offering something of value in exchange for an email. By acquiring an email address, you have a better chance to sell that customer as they become familiar with your brand and products." – Brett Farmiloe, Markitors

Read: The 3 Coolest Features of Medical Billing Software

5. Check Out Harvest

"Harvest is one of the best billing time-trackers out there. It has a simple, clean user interface. You can track multiple projects and clients at once. It also allows you to stay on top of your billable hours, reporting and budgeting. It's a must for anyone in client services or entrepreneur with their own business." – Jason GrillJGrill Media | Sock 101

6. Don't Automate

"Do it by hand for a while. Automation is great, but if this is the first time, be more manually and personally involved for a while. You’ll learn the ins and outs and then can start automating in places that matter." – Wade Foster, Zapier

7. Seek Out the Latest Tools

"There is a lot of innovation happening in the billing and sales automation space. Don't just settle for old tools. Actively check out new offerings. For example, RightSignature debuted a new credit card form within their contracts tool this summer. Plasso -- formerly SpaceBox -- has made upgrades to their platform, too. Get into a rhythm of researching the latest tools regularly so you don't miss an opportunity to simplify sales." – Doreen Bloch, Poshly Inc.

8. Use Quickbooks

"Use Quickbooks to send invoices. It gets emailed directly to your customer and they can pay with a variety of options. That payment then gets updated directly into your account system. It's very easy to use and setup." – Andy Karuza, Brandbuddee

9. Be Wary of Automation

"Be careful what you wish for, and customize the system to fit your culture. Automation is great, but it requires input. You need to mark if and when invoices are paid. You need to consider how frequently you should send reminders. Spend some time creating a system that makes sense for your business model." – Matthew Moisan, Moisan Legal, P.C.

10. Automate Your Collections With Personality

"We run a SaaS company and at any given time a certain percentage of customers' current months charges didn't go through. We tested the normal professional collections style emails versus reaching out to customers with personal and friendly emails. The personal emails worked much better to get customers payments back on track. Now we've automated the entire process with personal-feeling emails and voice mails; our save rate boosted significantly." – Trevor Mauch, Carrot

11. Communicate With Customers Throughout the Entire Billing Process

"You've almost made your first sale -- great! Now, does your customer know what to expect from your company next? A lot of first timeentrepreneurs drop the ball on laying out clear communication between the company and the customer. Using transactional emails and sending receipts will drastically increase the trust level between you and the customer. Services like Stripe and Chargify make it easy to implement this level of communication." – Lawrence Watkins, Great Black Speakers

Image Credit: Utah778 / Getty Images
Scott Gerber
Scott Gerber Member
Scott Gerber is the founder of Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most promising young entrepreneurs. In partnership with Citi, YEC recently launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses. Gerber is also a serial entrepreneur, regular TV commentator and author of the book Never Get a “Real” Job.