How to hire a bookkeeper in the cloud

Bookkeepers usually manage the smaller, day-to-day financial tasks such as accounts receivable, accounts payable, payroll, and reconciliations.

Unlike in-house hires who go through a process of face to face interviews, reference checks, and corporate screening, the hiring process for professional bookkeeper services or contractors online is quite different.
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The process of hiring an employee can be expensive and time consuming which makes hiring a professional bookkeeper service with a team who can ‘hit the ground running’ very attractive.  

We want to share with you a few pros and cons, questions to consider and ideas about hiring a bookkeeper offsite who will work "in the cloud."

The Pros:

​The professional bookkeeper or accountant who works remotely must have the expertise to “hit the ground running,” without investing in training. Since the bookkeeper is working remotely via the Internet and files are stored in the cloud, there are not additional expenses for supplies, space, and employee expenses. There is no vacation pay, unemployment or labor & industries taxes to be concerned with. Employment laws are not relevant since the agreement is a contract.

The Cons:

​An offsite bookkeeper working in the cloud might leave management with a sense of low or no control. With excellent communication processes in place, that feeling should be mitigated. An offsite bookkeeper sets their own hours and is evaluated based on the accuracy and timeliness of the work. ​
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The pros of outsourcing bookkeeping offer an advantage, but there is one more decision: Get services onsite or offsite via the cloud?

Here are questions to help you evaluate your needs:

WWhat type of bookkeeper do you currently have? Part time, full-time, in-house?

What specific reasons do you have for wanting a bookkeeper?  (Or to switch from your current bookkeeper?)

Is there anything you have tried with bookkeepers in the past didn't work?

Do you currently have accounting issues?

What goals do you have regarding your bookkeeping?

How frequently are data entry and reporting required? Daily/Weekly/Monthly/etc.

How often would you like to receive financial information about your business?

How soon after the day/week/month/period ends do you need financial reports?

Are there days you need to have reports compiled quickly?

What is your preference for receiving financial information about your business?

• In person
• Mail
• Email
• Via accounting software
• Internet – Cloud
• A Combination

Are you more comfortable with meeting in person, by phone, or via a web meeting?

Do you review reports in paper format or do you prefer on a computer/tablet?

Will your accounting software be located at your office, your bookkeeper’s office or online?

What accounting solution are you currently using? (e.g., QuickBooks or another accounting software solution, compilation or bookkeeping services, a manual ledger system, etc.) 

If you use QuickBooks, what version is your software?

Are there penalties, deadlines, audits or other issues requiring immediate attention?

What type of business?

• Sole Proprietor
• Partnership
• Corporation
• S Corporation
• LLC
• LLP

Do you have multiple team members who need the reports?

What is your industry?
     Do you sell liquor, tobacco or firearms?

Do you collect sales tax?
     Do you file by mail or online?

Are your financials ready for tax reporting?

Have you ever been surprised by an unexpected tax bill?

Do you need to track inventory?
            Do you use Excel, inventory software, ERP or accounting software?
            In-house? Or online?

Do you have a cash register, Point of Sale System or separate customer billing software?
     Is it connected to the Internet?

Do you sell online?
     Is your online store connected directly to your accounting software?

Are your statement accounts regularly reconciled? Do you have them available in paper or digital form?

Do you manage your checking account with paper, software or online?
     When was your checking account last reconciled?

Do you manage your loan payments with paper, software or online?
     If applicable, when were your loans last reconciled?

When were your credit cards last reconciled?

Do you manage your credit cards with paper, software or online?

Do you know how much revenue and profit your business made last month?

Do you rely on your bookkeeper’s advice for making financial decisions?
     Or do you prefer to search for answers online for making financial decisions?

Are bookkeeping responsibilities keeping you from other business-related tasks?

Who does your payroll?  A payroll service, in-house or other?

For payroll processing:

• How many employees do you have?
• Do they work onsite, offsite or mobile?
• How often do you issue payroll checks?
• How many days after payroll period ends are checks paid?
• Do you now, or would you like to offer direct deposit for payroll?
• Do you have employees in states other than Washington or Oregon?
•      Which states?
• Do you currently have high L&I or unemployment rates?
• Do you have employees who are in a union?
• Do you hire 1099 contract employees?
• Do you have commission based employees?
• Do you have tipped employees?
• How do employees track time? Paper, time-clock, in-house software or online?
• Does your payroll service or bookkeeper meet your needs and provide the reports to help you run your business well?

It is not required to know the answers to all of these questions. The bookkeeping company or professional can help you, and once they understand your business, they can also make recommendations.

These questions may become interview questions and it will soon become apparent which bookkeeper thoroughly understands your needs.

You may find that you need a professional bookkeeper to work part-time onsite and part-time offsite. Our team remains very flexible to meet your needs.  Our expert senior accountants and bookkeepers are available to work with your company  - whether you need us a few hours a day, a few hours a week, or a few hours a month.

How do you interview and hire an offsite bookkeeper who will work online and deliver your reports via a secure Internet system?  We prefer to first meet in person. While it is possible to share information via phone, web-meeting, and email, we know how important the role a bookkeeper is to your business and believe a face-to-face meeting at your place of business shows a commitment. Much of the future success is dependent on the connection, the communication, the ability to speak the same language with the same sense of urgency. 

After a good conversation or interview with several candidates, you will have a sense of both their character and their expertise. They will offer references, credentials, testimonials and outline what will happen next. A professional bookkeeping service will be not an employee needing training and direction; they will be a guide, remove stress and headaches, allowing you to focus on your business growth.

Eric Moore is our Washington Practice Leader and he will be happy to meet with you. He brings two decades of progressive experience in Controller, CFO, and General Management roles with privately held companies, and has a broad perspective from working in environments ranging from start-ups to multi-generational mid-market companies with revenue more than $100M.  

You can bring this list of questions with you to share your goals or ask about the best options. Our team can work part-time offsite via the Internet and keep you up to date. 

Please email Eric at [email protected] or contact him by phone:
Oregon (503) 473-0122 - Washington ​(425) 492-1901 - Toll Free (800) 931-6557