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6 Signs It’s Time To Outsource Your Bookkeeping, Accounting and HR Administration

6 Signs Its Time to Outsource Your Bookkeeping Accounting and HR Administration

As an entrepreneur running a digital health start-up before Stride, I dreamt of the times when a bolt of lightning would hit me and give me the answer I needed. Why did it always have to be so hard? Could someone please just tell me the answer so I can execute! Ha! Fat chance, it doesn’t work like that. In the world of business, building has many, many paths and there’s typically never a clear obvious, “no brainer” answer.

I realized I needed frameworks or a basis to make decisions. Better yet, a set of questions or circumstances that could be posed that would help clarify a path forward. We’re going to tackle that today on the topic of outsourcing accounting and finance. Why? Well, I don’t speak with anyone who doesn’t think it’s a great idea. But whether they are prepared to take action sometimes gets back to that lack of a framework for making decisions.

Here are our top 6 considerations when thinking about outsourcing:

1. You’re Planning A Financing

Whenever you are going to be in a position where your financials will be exposed and analyzed, you want to make sure they’re in great shape. It’s not the numbers but the signal to your investor, lender, or buyer that you run a disciplined, well-oiled machine. We have found companies that are well prepared to present financials and support that data with confidence can accrue a value premium in the market.

2. You Lost That One Key Employee

I’ve been there. When you feel that, if you lost that one person (maybe your bookkeeper of 5 years), the house would crumble. That’s a very vulnerable position to be in. But if it happens (and it often does), don’t get back into that position. Consider outsourcing to a team of people where there’s redundancy and the concern of a person walking out the door won’t be an issue again.

3. You Want To Run Leaner As An Organization

Non-core back office functions are more than just the expense. They are also employees that influence culture, consume resources, and create work. If you’re ready to really map your organization to the critical roles and responsibilities necessary to grow, which is usually product and sales, then it’s time to look at outsourcing.


4. You Know There Are Better Processes And Technologies Out There

Why are we still sending out paper invoices? Still making runs to the bank daily? Submitting expense reports by hand? There’s a better way that is often hard to see unless you work with a team that’s always scanning for new innovations to improve processes and streamline reporting.

5. You Are Spending More Personal Time On Back-Office

This is the killer but you often chalk it up to, “I do what it takes.” Yes, but the hero mentality is a disservice to the goals of the organization and why your investors and employees joined you. They didn’t commit so you could spend time on non-core functions, they committed for you to make a mark in this world. Don’t disappoint them.

6. You Need To Make Growth Investments This Year And Want Them To Be High ROI Initiatives

Back office accounting and finance is not a high ROI investment. Sales? Yes. Product? Yes. If you are going to use precious resources to begin scaling, they should be put on high return opportunities. Of course, the back-office needs to support growth, but it can be outsourced.


Stride was built to help business owners achieve financial freedom. That means allowing a business to focus its highest value resources on highest value impact. But often it’s unclear to many whether it’s the right time to outsource or the right circumstance. The 6 considerations above should be an effective guide in helping you assess. We are always ready to have a discussion to determine whether we are the best partner for you. You can reach us at hello@stride.services or contact us at www.strideservices.wpengine.com/#contact.


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