Everything You Need to Build a Team with Contractors


So your business keeps growing (yay!), you’re wanting more time to work “on” rather than “in” your business, or your life has changed and you’re looking for more free time outside of your company. Hell, it could totally be a combination of all three! Which leads you to do what the majority of any other business owner would do - hire one or more subcontractors to help lighten your workload.

There are two main areas you can hire subcontractors to help with:

  • Client Facing (client work, invoicing, payment follow ups, client work research or data projects, etc)

  • Behind the Scenes (email, graphics design, social media management, accounting, content creation, etc)

When you get ready to hire a subcontractor or business support, you’ll want to make sure that you’re both a solid fit for one another. A few tried and true processes for me include:

  • Making your initial posting as clear as possible (include details about yourself, your business, the responsibilities you’re looking for help with, and any make or break characteristics)

  • Running on a trial or test period for your initial engagement after which point you can both review the working relationship

  • Having a password management system setup (like LastPass)

  • Most importantly, following your intuition. More often that not, you’ll have an initial nudge one way or another about someone and I recommend you follow it.

As you start to build a team, you’ll want to decide if you want to run your business as an agency with multiple associates or subcontractors assisting in the day to day client work, or as a more robust version of yourself. Quite a few of the digital marketing or copywriting clients I work with have chosen to run their businesses under an agency model. Whereas, a lot of legal, photography, or finance (like me) businesses have chosen to hire out everything except the high value strategic client work.

For an idea of how this can work in your business, I’ll walk you through what’s been working in mine! I regularly work with five different subcontractors, but only one of them assists with client work regularly. The five of them handle the following:

  • OBM (Online Business Manager) - think of her as the architect behind a lot of my business. She knows where I’m driving, what my goals are, and regularly interfaces with my team to make sure projects I envision are executed by the relevant parties. She’s also integral in making sure blogs, emails, and social media posts are regularly scheduled across multiple channels.

  • VA (Virtual Assistant) - handles anything and everything I can think of offloading to her - snapping images of client receipts and uploading them to my client portal, helping with social media tasks, and more.

  • Bookkeeper - helps with one-off client projects and on-going client categorizations and reconciliations. She also continues the same level of client care and responsiveness while I’m out of the office or on vacation.

  • Graphic Designer/SquareSpace Guru - manages regular website updates, branding or logo changes, any customization to my course site or website revamps, and all presentations and graphics for my courses.

  • Pinterest Manager - the newest team addition, she’s helping grow and optimize my Pinterest to help achieve some bigger goals I have for the year and has been a huge help with optimizing my blog graphics, too. 

In the past four years since I started working with my first contractor, I’ve gone through approximately 4 bookkeepers, 1 drama-filled OBM situation, and 3 other miscellaneous contractors. You could say I’ve kissed a few frogs, but wow have I ever found my all star contract team now! So, keep that in mind, if you don’t find the right person or people immediately, keep trying. Refine your process and keep going until you find your team. The ones where you can build a relationship and a thriving business together. The ones that have complementary work style and personalities to yours, and help round out your business.

It may look like I’ve outsourced most of my business, but for now, there are still a fair number of responsibilities I’ve chosen to continue handling myself:

  • 90% of client interfaces/communications

  • All sales/prospect calls

  • Proposal and contract creation

  • Invoices and client billing setup

  • All training packages

  • Course content creation

  • Content creation (blogs, newsletters, social media posts, etc)

  • Emails and social media messages (working on transitioning out of the daily on this)

At the end of the day, while what I do can be replicated, I have a unique skill set and background, and I’m not willing to hand over the reins to anyone else at this point in time. I’ve blurred the lines of my business and lifestyle (intentionally), and as such, feel it’s important to continue being the driving force at the front and center of my company. Which means that out of necessity for my time and sanity, ALL of the admin or daily tasks that can be handed off to someone that can do them as good or better than me, must be delegated in order for me to devote the time and energy to my clients and myself that we deserve! By delegating what I can, it frees up both my time and my creative energy, so I can pour what I’m good at into my business, my clients, and my content!

If you’re looking to build out your team as your business evolves, you can learn more about growing your business and your team in my in depth, all-the-things-you-need to know course. Finance University for the Self-Employed (FUSE) is THE comprehensive course that I created from scratch to cover all of the most common accounting, finance, tax, and pricing situations you’ll encounter as a business owner. Learn how to navigate all of the financial nitty gritty like the badass you know you are - be the first to hear when it opens for enrollment by signing up here.

Katelyn Stanton