With seemingly endless software offerings for payroll, employee scheduling, payments, and inventory, the modern business owner is pursued in a way that is almost unrecognizably different to my own experience 10 years ago.

The last decade has brought about a technological sea-change on Main Street. Local business owners are now hot property in Silicon Valley and countless startups are releasing a slew of cloud-based tools targeted towards the SMBs. It’s a big change, and I speak with owners every day who are excited to take advantage. But all too often they are overwhelmed by the range of available options.

So how can business owners reduce the stress of choice, and make the right decisions about software investment? There are three key rules to implement:

One thing at a time

Anyone who tries to select accounting software, email marketing tools, and scheduling automation all at once is bound to make a bad choice. You don’t need every bit of software out there, so your first job is to prioritize tools that will really make a difference, then create a calendar of software you’d like to try out. You want tools that will give you more time, money and data. Don’t underestimate the time component in this equation.

Reduce your choices

Once you have a prioritized list of software to try, go through providers and find reasons to reduce the choices available to you. Speak with other business owners, consult third-party review sites and use app store reviews to get an initial impression of the products.

Treat everything as a test

Most business software providers offer free trials and a SaaS monthly subscription that can be canceled at any time. If you choose this kind of provider, you give yourself a chance to measure every penny you spend as an investment – not a cost. The key to a clear-headed evaluation of your available options is testing the impact each software solution has on your business in a real-world environment.

For example, you can measure the number of hours you spend doing payroll each week, and then only implement the payroll software if it saves you time during the trial period. Again, run these tests one at a time in a measured manner. And don’t forget, ease of use is every bit as important as the features offered.

Kick the tires of customer care support

Quality customer support is a huge time saver in moments of crisis and a big part of the investment you’re making. It’s not enough to test drive the product; you have to have to test drive the support services behind the product too. Some companies will tell you their software is “so simple you’ll never need to call.” but in my experience that’s just code for “we can’t be bothered paying for a customer care team.”

If you’re feeling trapped in the software jam, consider reducing the burden of too much choice. Go one at a time, reduce your list, test the tools in the real world and look for partners you can reach on the phone.

Nick Kaptain admits he didn’t know the difference between a bookkeeper and an accountant in 2009 when he launched Adlava, a web design, video production, and digital marketing firm based in Las Vegas. He hired a part-time bookkeeper and assumed that was all he needed.

“It was hard enough to focus on getting business and staying afloat,” Kaptain says. “Here was someone I could pay for 30 minutes or an hour a week to manage all my transactions.”

But as the tax year ended, Kaptain realized he had made some poor financial choices, such as not spending money on expenses that would have been tax-deductible. The company wound up with a large tax bill as a result. Kaptain realized his bookkeeper wasn’t equipped to offer the kind of long-term financial planning he needed.

His takeaway from the experience: “Definitely hire a CPA. They know more about tax strategies and can help prepare you over the course of the year.”

The difference between bookkeepers and accountants

The bookkeeper and the accountant have complementary roles, but they are not interchangeable. A bookkeeper deals with transactions – entering account data, paying invoices, and balancing the books. An accountant will use that data to run more sophisticated analysis of your business’s financial situation and outlook, and help with tax planning. Online tools such as QuickBooks and Bill.com make it easier for these professionals to share information in real time when they’re not in the same location. As Kaptain says, “The bookkeeper knows what the accountant wants to see.”

After starting up and operating a small chain of wine shops in Brooklyn, New York, Jason Richelson created ShopKeep, a point-of-sales system for small businesses that funnels data into online bookkeeping software. Retail businesses in particular have a lot of cash transactions that need to be entered daily, Richelson says. That’s the job of a bookkeeper, he says – to handle the data entry that’s time-consuming for the business owner.

When Richelson was running his wine company, the Green Grape, it grew from one to three stores quickly. And the company’s bookkeeping needs grew as well. “We were used to getting one or two deliveries of inventory a day, and then it was 20,” Richelson says. The growth also meant more employees and more paychecks to cut, which meant more work for the bookkeeper.

Using an accountant from the beginning

For the most part, a bookkeeper can’t offer guidance on taxes, acquisitions, or exit strategies. Issues like these require the expertise of an accountant. The question then becomes: when do you need an ongoing relationship with an accountant for your small business? And how often should you meet?

Tax accountant Andrew Poulos, principal of Poulos Accounting & Consulting in Atlanta, says an accountant can be useful from the beginning in an advisory capacity. They can help entrepreneurs choose the right kind of structure and entity for their business, and can advise whether to classify workers as employees or contractors. Poulos says many business owners make early mistakes in these areas that are easy to avoid with the proper guidance.

“The one place you don’t want to cut corners is the accounting aspect,” Poulos says. “Unfortunately, we live in a day and age where tax laws are complex, and it doesn’t take much to get it wrong.”

A business owner may discover that it makes sense to incorporate as an LLC or an S Corp because it’s more favorable than paying the self-employment tax rate. Poulos says it’s also helpful to have an accountant set up payroll tax withholding– a task that many business owners fumble.

An accountant can also help a business set up its initial metrics, says Michael Paull, a CPA who has served as advisory chief financial officer to companies in multiple industries. “A lot of business owners like to grow into the need for an accountant,” Paull says. “But there’s certainly a benefit to starting with one.”

Growing into the need

Some business owners are comfortable checking in with an accountant a few times a year. Poulos recommends two to four consultations a year at minimum in order to stay on top of your tax situation. “If you come to me once the year is closed, I can’t do any tax planning for you,” he says.

Accountants also have the analytical skills that can help improve operations or identify growth opportunities, Paull says. For instance, a business owner may have a good sense of which products sell quickly and which move slowly. But he or she may not realize what’s happening with inventory in the middle. An accountant could recommend products to drop or to bundle, or suggest price adjustments.

“A good accountant is a thought partner. They can bring best practices to your business,” Paull says. “An accountant is in a good catbird seat to have a handle on costs and the market. They may see an opportunity that a business owner wouldn’t.”

It’s also important for business owners to see that accounting needs are dynamic, not static, says George Malina, partner-in-charge of the accounting services practice for Sikich LLP, a professional services firm specializing in accounting, technology, investment banking and advisory services, based in Naperville, Illinois. Certain occasions call for more hands-on involvement, Malina says, such as when a merger or acquisition is being considered, or when the business is being passed on to the founder’s children.

A worthwhile expense

Small business owners with limited cash flow may hesitate to pay for more than a couple hours of bookkeeping a month. But accountants say their time is a small investment with the potential to save big money in the long run.

Accounting mistakes can be expensive, Poulos notes. Compare the expense of meeting with a financial adviser a few times a year – maybe at $100 an hour – to the cost of a tax audit, which can average $3,000 in accountant’s fees alone.

Malina says business owners who try to handle their finances alone are also giving up the opportunity to generate income. “Just do a simple calculation,” Malina advises. “If you’re spending 10 hours a week on bookkeeping and accounting, and you’re not even sure it’s right, what could you do with that time that would be more valuable?”

Finding a good fit

The business owner and the accountant should have a close working relationship. So it’s important to find someone who’s not only trustworthy but also compatible with you. Start by asking fellow entrepreneurs for recommendations on both bookkeepers and accountants, and consider whether hiring an individual or a service is a better fit. Poulos advises using only a licensed professional: either a CPA or tax accountant who, like Poulos, is an enrolled agent licensed by the U.S. Treasury.

Kaptain agrees that hiring professionals helps you look professional, too. He values the input he gets from both his bookkeeper and his accountant. Just as importantly, he’s comfortable with them.

“I ask my bookkeeper and my accountant for advice on all types of things. It’s nice to have strong relationship for that,” Kaptain says.

Disclaimer: Since the details of your situation are unique, you should always seek the services of a qualified professional for advice specific to your business.

Today in Small Business: The Year’s Best Franchises

The New York Times

ShopKeep also officially rolled out Apple Pay support on Monday to go along with the new reader. The latest update of the ShopKeep app, version 2.5.2, supports Apple Pay, contactless and magstripe cards.

The company also said it “will support” EMV chip cards sometime before the October 2015 “liability shift” deadline, after which merchants who can’t accept EMV chip cards will be liable for any fraudulent card purchases they accept. ShopKeep didn’t spell out when that will happen; some large banks are already issuing EMV cards, and several big retail chains are already committed to accepting the cards by the end of January 2015.

ShopKeep co-CEO Norm Merritt told Re/code that his merchants haven’t been demanding NFC equipment to accept Apple Pay, but he said he believes as mobile payment becomes more popular, more small businesses will want to accept it. Partnering with Ingenico also means ShopKeep can get an EMV reader into its customers’ hands before Square, which is taking preorders for a $29 device EMV-only card reader.

ShopKeep, a startup that makes checkout software for brick-and-mortar stores, has a new deal for new customers: Free equipment that allows them to accept mobile payment methods such as Apple Pay, in addition to a new, more secure type of credit card.

The equipment, which will cost current ShopKeep customers $259, includes a technology called near field communication, or NFC, that allows customers to pay using information stored on their phones. Apple Pay and Google Wallet use this technology as the backbone of their payment products.

Perhaps more importantly, the equipment can also be used to accept a new type of credit card — known as EMV chip cards — that are currently being issued by credit card companies in the U.S. to help reduce credit card fraud. The EMV card technology, named after the original technology developers Europass, MasterCard and Visa, has been common in Europe for a decade and makes cards harder to clone than the traditional credit cards that are still common in the U.S.

The giveaway underscores the fierce competition among young companies such as ShopKeep, Square and Poynt, as well as bigger players like First Data, to get small businesses to ditch their clunky point-of-sale equipment for newer, modernized checkout software and hardware. It also highlights the lead these businesses are taking in trying to convince small businesses that they should upgrade their equipment in order to accept the new type of credit cards that big retailers have been gearing up to accept.

“We see ourselves as the IT departments for these growing merchants so we want them to have the latest technology,” said Norm Merritt, ShopKeep’s co-CEO.

Merritt admitted that ShopKeep merchants, of which there are currently about 11,000, haven’t been knocking down his door demanding NFC equipment to accept Apple Pay. But he believes mobile payment methods such as Apple Pay will become more popular in the future and that more small businesses will then want to accept it.

He also said the giveaway, which should help merchants reduce fraud liability from fraudulent card purchases, aligns with the company’s mission of supporting small businesses. Beginning in October 2015, liability for credit card fraud will sit with whichever entity — the issuer or the merchant — is still using the less-secure equipment.

The common belief in industry circles is that small businesses will be slower to upgrade their equipment to accept chip cards than big retail chains because of the equipment’s cost and the relatively low rate of fraud in their stores. Merritt believes that ShopKeep is significantly reducing the friction that is stopping them from upgrading.

ShopKeep is based in New York City and has 170 employees. It charges businesses $49 a month, per register, to use the ShopKeep software to manage transactions, inventory and customer information. Its software is made to run on an iPad, which it sells along with cash drawers, receipt printers and other equipment used by restaurants, bars and specialty retail shops.

ShopKeep businesses can use any credit card processor to accept credit and debit card payments. In theory, a business could use Square as its payment processor and ShopKeep as its software provider. Merritt, however, says this is rare.

Square said last month that it would begin taking preorders for a $29 device that would allow merchants to accept chip cards. The device does not include NFC technology and does not include a keypad like ShopKeep’s that can be used by chip card holders to punch in their PIN to authorize a transaction. These PINs are commonly used in conjunction with chip cards in Europe, but some U.S. banks are allowing their customers to initially provide their signature in place of a PIN.