From Freelancing to Growing your Team

From freelancing to growing your team | Spruce Rd. | In this recorded workshop I share how I made the transition from freelancer to collaborating with other designers. This has helped my business grow and expand, and I hope it helps you gain clarity on how to structure your business!

Last week, during the final episode of this lunch + learn season, I shared how I went from freelancing to now working with a team. This has been such a huge transition for my business, and one that has allowed Spruce Rd. to grow. Though this was definitely the right move for my brand, I am by no means encouraging every freelancer to start working with a team. This completely depends on your brand, and is a business model you have to feel comfortable with for your business + life. In the workshop recording below I share a few tips (+ answer your questions!) on how this model has worked out for my team. I hope it helps you gain clarity on how to best structure your brand.


In January of 2015 (about a year ago), I started my own business. I set out as a freelancer, with zero overlap from a previous job where I wasn’t allowed to freelance on the side. I always knew that I wanted to grow my business beyond just freelancing over the years, so I had a long-term approach from the beginning. I knew at some point my husband and I would have kids, so I didn’t want to feel tied down with each client project, or put my business on hold every time I was on maternity leave. Not only that, I knew I would be limited in how far Spruce Rd. could reach if I reduced it down to only tasks I could complete. That is a recipe for an over-worked, stressful lifestyle that I was not ready to accept!

I have waited to share my insight to this process until I gained more experience with my team. Since hiring a team, I have sub-contracted 9 client projects, each of them with a successful and happy client, as well as designer upon completion. I’m confident in my process, the designers I work with consistently, and ready to share what has worked for our team!

Why switch to a “team” model rather than “freelancer”:

Though switching to a team model might not be for everyone, I wanted to share a few reasons why it might be the best for your brand.

  • You are eager to work on side projects, and build your brand, but the client work demands all of your time
  • You feel overworked, and stressed out handling the business, bookkeeping, marketing, and client work
  • In thinking long-term, you would like to trust your business in other capable hands
  • You think your brand could benefit from different skillets, perspectives or aesthetics (if a designer)
  • You are booked out several months in advance

When to make the switch:

As it is always said… “better sooner than later.” This mantra holds true for when looking to start working with a team. Honestly, I did not wait until I made $100k when I started hiring. I knew I would grow my team, and I started getting more project inquiries that I couldn’t pass up on. I could have offered to book them a month or two in advance, but that business model never resonated with me. It seems like a disservice to the client to make them wait months for their project to begin. It also starts the project on a somewhat sour note in that they had to wait so long. Nobody likes to wait, so instead of booking out I grew my team. Technically, Spruce Rd. could have remained just me if I booked out in advance, however that system doesn’t seem like it is built to last.

Think about it, if you are consistently booked out you are most likely exponentially growing your inquiries each month / year that passes. So if you are booked out a full year ahead, your inbox probably continuously receives an increasing about new leads each month. This is not a structure built for longevity… it is a short-term band-aid solution.

Rather than entertain the idea of getting booked out, I encourage you to grow your team earlier than necessary so you can take on more projects that are the right fit. It truly is a win/win. The client is thrilled you have availability. The designer is happy they have a great freelance project. You, as the owner, are happy you can step away.

How to structure your team:

There are several ways you can structure your team of sub-contractors. What has worked best for me is to hire designers to work on the client side of Spruce Rd. I work with brand identity designers, an illustrator, and Squarespace designers at the moment. I have a list of other collaborations including copywriters, photographers, letterers, Wordpress + Shopify designers, developers, assistants etc. Through having these other potential collaborations, I’m ready to accept projects that otherwise I could not take on.

Here are a few ways you can structure your team:

  • Hire sub-contractors to handle client work
  • Hire a project manager to assist in setting up each project
  • Work with copywriters for your marketing materials
  • Collaborate with an assistant to manage email inquiries, tasks, proof-reading, etc.
  • Hire a social media manager
  • Work with a writer to create content marketing for your brand

Tips on how to grow your team:

  1. Only work with the best Select subcontractors that you truly think are at your same skill set, or preferably better than you. This takes a little humility, but I truly think this is the only way to go about building a successful team. The designers I work with always send me proofs before the client views them, and I hardly have revisions, if any. They always blow me away and get me excited! This is the proof of hiring the right people.
  2. Encourage transparent communication Rather than remaining the main contact for the client, I trust my designers to interact with the client directly. This opens up communication, and allows for transparency in the process. I much prefer this, over somehow hiding that I didn’t design the work. When I previously worked at a design studio for a brief time, they wouldn’t allow me to talk to clients. This was a shock to me, since my previous experience of 4 years always allowed open communication. It is damaging to the relationship between the owner + contractor if you don’t trust them with the clients. In order to build a lasting relationship with your contractor (remember, you think they are better than you!), trust them with your business.
  3. Establish clear systems Before hiring a team, I had loose processes in place. Once I knew I was hiring, I quickly got everything together and created clear systems for my client process. I created a Google Drive folder for my team, that included the step-by-step process, branding templates, examples of previous work, and even swipe files to send to the client. This has made for a seamless process, and limited questions from the designers. They can always reference the Google folder to anticipate what is next in the project.
  4. Always have a contract + W9 Though I am still finessing my designer contract, I realize it is important to always have a contract between you (the owner) and the sub-contractor, as well as a W9. I won’t go into too many details here, because I highly recommend talking to your accountant + lawyer (like I did) to make sure these documents are accurate. You want to protect your business, as well as set it up correctly, so don’t forget these documents. A few terms I included in my designer contract was to prohibit the designer from working directly with the client, outside of Spruce Rd. for a certain period of time, they can’t re-purpose/sell any of the processes or templates I created for them, they agree to meet deadlines, etc. Just think through what you would like protected, and put it in writing.
  5. Let them take the reigns As the “creative director” I actually do little directing. As mentioned before, I work with the best designers + illustrators, so I don’t feel it is necessary for me to have my toes in every project. Of course, I am there for them throughout the process and approve the proofs before the client sees them. I think it is a much healthier + better structure to allow your sub-contractors to take the reigns. For instance, the illustrator I work with always knocks my socks off when I receive a proof. She comes up with the most creative concepts, has killer design work, and a skill set that I have no business interfering with. Why would I want to stifle her process? I’m always there to provide suggestions, and by no means am I an absent creative director, but I avoid becoming that back seat driver to the designers. Through allowing them to take the reigns, they are more invested in the project, develop creative + unique solutions, and are more excited about the work they are doing.

I hope that this insight to how I created a team for Spruce Rd. encourages you to think long-term about your brand, and how you can grow your business. It truly has made the largest impact on my business, and has had such a positive result with my brand, as well as the clients.