A Guide for Working With Design Freelancers and Creative Studios

Designer Fund
Sep 21 · 19 min read

Nearly every startup needs creative help at some point in their lifecycle — often during key inflection points, such as raising funds, up-leveling into a new market, or communicating who they are to the world for the very first time. Freelancers, studios, and agencies can also be more than just an extra pair of hands; they can be strategic thought partners, helping you create work that is core to your business.

At Designer Fund, we have seen many productive, inspiring pairings between our portfolio companies and their external creative partners. But we also see folks struggle to hire someone for the first time, find a good fit, or get quality work out of the relationship.

In a sea of creative vendors, how do you make sure you have the right early conversations, screen candidates, and make a great impression yourself? How can you structure a partnership to produce the best work possible?

In this guide, we’ll pass along best practices we’ve uncovered over years of hiring creatives and acting as a design advisor to startups. You’ll also hear tips from our design community — not just from clients, such as founders and heads of design, marketing, and brand, but from service providers themselves.

This guide will help you build long-lasting, fruitful relationships with creative service providers who can bring your visions to life.

I. Figure out what you need

Start by understanding the project (and yourself) better. We’ll help you clarify what you need and what resources you have available, which will fast-track you to the right match. We’ll also look at the pros and cons of freelancers, studios, and larger agencies.

II. Select the right creative partner

This section is all about the search: getting vendor referrals, vetting their portfolios, which questions to ask during screening conversations, and what to put in the contract before you kick off a project.

III. Create great work together

Finding a partner isn’t the end goal. Creating excellent work is. We’ll show you how to get the most out of your relationship, from laying guardrails for collaboration to giving effective feedback to troubleshooting when the work isn’t up to par.

There’s no better feeling than executing more effectively or wrapping up a project engagement with a great partner and launching it to success — whether it’s a funding round, a critically acclaimed rebrand, or a product that expands your customer base. When you have the right team, anything is possible.

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I. Figure out what you need

Take a self-assessment: What kind of help is right for you?

The first step is to take stock of your needs, your resources, and how you’d like to collaborate.

Getting clear about this early on will help you develop an effective creative brief and direct you to the right people during your search.

Things to consider:

  • Budget — What type of service provider is likely to work for your current and future budgets?
  • Thought partnership — Do you need a thought partner who can help you with strategy development, creative direction, and/or laying the foundation for your company identity? Or do you just want an extra pair of hands to execute your ideas?
  • Your design system — Do you have an established design system? If yes, do you have internal reviewers who can reliably give freelancers feedback on how their work fits in?
  • Project scope — Is the project well defined, or do you need someone’s help to plan it?
  • Embedding the partner into your team — Would you like someone to work directly with your in-house designers, engineers, and/or marketers? To work in your Slack channels and project management software, or attend design meetings?
  • Internal development resources — Do you have a development team that can build designs once an external partner hands them off? Or do you need a team that can design, develop, and launch a project end to end?
  • Closeness — How often do you want to talk live? Are you okay with a partially or fully remote team?
  • Future needs — Will you want to work with the same service provider for upcoming projects? What skill sets and headcount do you anticipate you’ll need?

Next, operationalize those needs into a creative brief document for the specific project you’re hiring for, which will guide your search.

Write a creative brief

A creative brief is your opportunity to get consensus from your team and any project stakeholders so everyone is aligned on goals, budget, and scope.

You can also share the brief with vendor candidates during your search to make discussions efficient, and use it as a basis for your project contract.

Briefs are so, so important. If you don’t set things up correctly, you can waste a lot of time and money, and potentially ruin your relationship with the folks you hire.

Micah Panama, Creative Director at Gusto

Your creative brief must include:

  • Goals. This is perhaps the most important part. Why are you investing your company’s time and money into this project? What do you hope to achieve?
  • Success metrics
  • Key teammates, stakeholders, and decision makers
  • Constraints (budget, deadlines, business milestones)
  • Deliverables

You can also include unknowns and questions to ask, and a section describing your audience — it’s important that your creative partners understand who you’re talking to.

View a sample creative brief template here.

Types of creative service providers

Now that you know what you need, see which type of provider will most likely fit best. We can group most creative service providers by size into the broad categories of freelancer, studio, and agency.

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That said, creative and design support comes in many shapes and sizes. Each of these three types tends to come with pros and cons innate to their structure, but there are many exceptions to the rules. Each provider works a little differently and puts their own spin on things. The following information about categories is simply intended to inspire questions during the vetting process and to guide your thinking about fit.

We regularly hire freelancers and studios to increase capacity, or for specialization. For example, we don’t have an in-house video editor, so we often hire freelancers to work with our internal teams.

When Gusto was ready to kick off our big rebrand, we needed more capacity, but we also wanted to have branding experts in the room. There are so many projects where it’s necessary or helpful to bring in an outside creative partner.

Micah Panama, Creative Director at Gusto

Meet the archetypes: Freelancer, Studio, and Agency

Freelancer

The archetype: A solo designer for hire.

Freelancers often gain experience in-house or at an agency before striking out on their own. Many choose freelancing for improved work-life balance or for more control over the types of clients and projects they take on.

Benefits:

  • They are often more cost-effective due to less overhead.
  • You have direct access to the creative talent, and you know what you’re getting.
  • It’s often easier and quicker to get started.
  • They can be embedded into a team easily.
  • There may be potential for contract-to-hire.

Considerations:

  • Since they’re just one person, the creative work may be limited to their expertise or aesthetic.
  • They may not be able to jump into an adjacent project that requires capabilities beyond their scope.
  • It’s best if you already have a design system in place and internal reviewers who can provide feedback and ensure that the freelancer’s work fits within it. It can be unfair to ask a freelancer to develop a design system around a one-off project, unless that is their expertise.
  • They have finite availability, which could cause problems if your timeline changes, or it could limit your future work together if it grows.
  • They may be excellent at creative work but lack business skills — which could make the logistics, or their relationship with you, bumpy.

Freelancers can be faster and more cost effective, and for the most part you know who you are getting. To me, they are an extra set of hands. I’ll often hire a freelancer when I need production work because I don’t have bandwidth in house — or when I already have a really strong relationship with someone who has the specific expertise I want, and have already established trust.

Emily Kramer, Former Head of Marketing at Carta and Asana

Small boutique studio

The archetype: A small core team that can pull together larger, ad-hoc teams tailored to specific projects.

For example, a studio might consist of two full-time employees: a design director and a strategist. For a new project, they might also bring in a freelance designer, a writer, or an illustrator, depending on project needs.

Benefits:

  • It is often more cost-effective to work with a small studio than a large agency.
  • You regularly and directly interact with the individuals who are doing the work.
  • They can provide a larger range of capabilities than a single freelancer.
  • Turnaround time can be faster than with a larger agency.
  • They tend to be flexible, hands-on, nimble, and more easily adaptable to your in-house process and collaboration tools.
  • They can meet a wide variety of current and future needs by assembling talent as needed. Teams are multidisciplinary, despite their small size.

Considerations:

  • The budget to work with a studio can be larger than with a freelancer.
  • A studio may not be set up to handle large-scale, long-term projects or a wider variety of services.
  • Their ability to give you the right size and type of team depends on their network of talent.
  • They may not be able to give you a dedicated account manager, and may not have a big portfolio, compared to agencies.

I typically seek out a studio in the scenario where I need or want broader creative direction. When I don’t have any designers in-house, I tend to avoid hiring a freelancer for this purpose. The freelancer will be put in a position where they are forced to shape the broader creative direction for the product or company. This can be very difficult to navigate without an in-house partner.

Emily Kramer, Former Head of Marketing at Carta and Asana

Medium-to-large agency

The archetype: A large company with a well-established brand name and a roster of full-time employees, such as partners, creative directors, junior and senior designers, strategists, writers, account managers, accounting personnel, and other specialists.

A medium-sized agency may have around 10–30 full-timers; large agencies, upwards of 50. They also bring in freelancers as needed. Teammates may either be dedicated to your project or splitting their time among other clients.

Example team #1: creative director, production lead, two designers, developer, strategist, account manager

Example team #2: design director, design lead, product designers, specialists as needed, solutions architect, UX researcher, engineering, and a producer and client partner as support staff

Benefits:

  • They give you access to a very large range of capabilities, talents, and concepts to work with.
  • They can often cross-pollinate ideas if they span industries and business models.
  • Senior leadership and designers may have deep experience and connections you can benefit from.
  • They can provide an elevated level of client service with dedicated managers and admin.
  • They can easily staff a large team dedicated to your project and scale up to accommodate future work.
  • They typically have a substantial and varied work portfolio.

Considerations:

  • Agencies are the most expensive option.
  • Some can be rigid in their process; for example, they may not want to use your creative processes or collaboration tools (though there are certainly agencies that do work embedded).
  • You may have limited face-to-face contact with the whole team working on your project, and you may not always know up front who will be staffed, unless you ask.
  • The work cycles can be a lot longer.

For a startup, I’d work with a big agency once every five years in a company’s lifecycle. In my experience, large agencies equal a lot of overhead, and things take more time. But they can be great for a huge project with multiple channels, disciplines, and media — like a rebrand with a new website, brand video, and brand campaign.

Emily Kramer, Former Head of Marketing at Carta and Asana

Do you want scale or do you want speciality? Getting clear on that is really important. Independent freelancers might be great if you need someone to pop in as an extension of your team. If you are a 20-person startup looking to redo your website, a small studio might be great for you. If you’re a 300-person, multi-billion-dollar company, or for anything that’s going to be a bigger, long-term project with a fully staffed team, a bigger agency can be better.

Micah Panama, Creative Director at Gusto

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II. Select the right creative partner

How do you know which vendor is right for you? Let’s talk about vetting, what to expect, and what to look out for when signing an agreement.

Tips for finding outside creative help

Lean on design-minded investors, like Designer Fund ;)

Good investors and partners cultivate relationships with studios and freelancers, and they can help with scoping, creative direction, and design feedback throughout the process.

Ask for referrals

Start your search by asking for vendor recommendations from:

  • Your investors
  • Your colleagues in a similar role at a different company
  • Freelancers and studios you’ve worked with before (independent writers have probably worked with great designers, and vice versa)
  • Online groups you belong to

Include key info in referral requests

When you ask for a referral, send along your creative brief for reference, or make sure you include these key pieces of information to save everyone’s time:

  • Name and URL of the client company
  • Timing of the engagement (confirm they are available)
  • Budget range
  • Core skills needed
  • Whether it’s remote or location-based

Look outside your area

Opening your search to remote workers gives you access to amazing talent. If you’re in an expensive location like the Bay Area or New York, you can often find creatives elsewhere at a lower cost or with more schedule availability.

The first pass

Carefully look through a vendor’s online presence before getting on the phone.

Look at their portfolio

Evaluate their work for quality, attention to detail, and polish. If you don’t have design experience, ask a designer friend or an investor to help assess the work for you.

It’s not always important for a provider to have experience in your industry, and you can benefit from cross-pollination if they’ve worked on analogous problems in different verticals or for companies that are at a similar stage of growth.

Client wise, we love early stage companies and we’re industry agnostic. We take on a diversity of challenges and can bring product ideas from one industry to another. We’ll spin up a smaller team that is dedicated to a project for a longer period of time and gets embedded in the client team.

Luke Des Cotes, VP of Partnerships, MetaLab, large agency

Search for specialization, unique strengths, and point of view

What is their secret sauce? Check whether they are generalists or specialists (e.g., illustration, product UI, motion design). If they claim to “do everything,” it can be a little harder to figure out what they truly excel at. Take the time to dig deeper to find their strengths.

Check for social proof

Have they worked with companies similar to yours? Look for testimonials from people you relate to professionally.

Set up an exploratory call

Next, schedule a 30-minute introductory conversation to assess mutual fit.

Send the vendor your discussion topics ahead of time for an efficient meeting (e.g., On the call, I’d like to discuss…).

The most important questions in an introductory call:

  1. Could you walk me through a past project or two that is similar in scope to mine?
  2. Could you walk me through your process?
  3. Do you have any questions about what we need done and the creative brief [if shared]?

Additionally, you may cover:

  • What are your strengths and weaknesses as a studio?
  • Who will be staffed on my project, and can I meet them?
  • What is your communication style? Do you prefer phone calls, video calls, emails, Slack, in-person meetings?
  • What design and collaboration tools do you use, and are you willing to join me on the platforms my company uses?
  • How will you interact with in-house designers [if applicable]?
  • How will you interact with product teams [or marketing, engineering, etc.]?
  • Anything else you’d like to share?

Being an agency is often like being a therapist for our clients. Sometimes our job is just to listen and mirror back to help you craft the narrative and craft the product.

Halli Thorleifsson, Design Director at Ueno, large agency

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Vet responsibly

Remember, vendors are people too. Be respectful of their time and attention because introductory phone calls and proposals are not paid work.

And they will be vetting you right back. If you want to work with top designers, you need to be an attractive client. The best collaborators will be evaluating your project for greater meaning, opportunities it could create, and the quality of the relationship.

Expect to have several conversations to establish rapport and determine mutual fit. Here are a few things creatives look for, and tips on how to put your best foot forward.

Vetiquette

  • Request proposals only from creative partners you are seriously considering. Putting together a quote or proposal is a lot of (unpaid) work for a freelancer, studio, or agency. Make sure to follow up with everyone who sends you one.
  • When you can, share your budget up front, as soon as possible. Budget is a fast, decisive determinant of whether a provider can take on your project or not. It’s okay if it’s just a range, but do provide some numbers to ensure you don’t waste anyone’s time.
  • Be transparent about your timeline and how many other vendors you’re considering.
  • If you have been deep in talks with a studio and decide to pass, let them know. Don’t go dark.
  • Come prepared to provide basic details about your business model, team structure, and process.
  • Communicate reasons why you would be a good partner to work with. How does your company make a positive impact on the world? What value does your product bring to customers? Do you have an exciting vision, mission, or history? What is your company culture like when it comes to collaboration?
  • If your leadership values design and has a track record of investing in it, highlight this.
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Sign an agreement

Once you’ve selected your creative partner, you’ll want to put your partnership in writing with two documents:

(1) Master services agreement or Contractor agreement: This overarching contract governs the relationship between you and the vendor.

(2) Statement of work: This details the work to be done for a specific project. The SOW sits under the master services agreement, and can be replaced with new SOWs if a project changes or you start a new one.

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III. Create great work together

Finding a great creative partner can feel like a honeymoon. But you’ll still need to deliver feedback. And, occasionally, you may need to troubleshoot disappointing work. Put a few guardrails in place at the start of the project to ensure a smooth, long-term relationship.

Identify the main point of contact on the client side

An internal contact must carry the torch for the project. They’ll drive the work forward and synthesize all feedback, ensuring that it’s consistent before sharing it with external creative partners.

This person makes sure the work calendar is set and milestones are agreed upon. They keep the team moving on both ends. You just need someone who is organized and connected. It could be a creative producer, a marketing manager, or someone in an admin role.

Micah Panama, Creative Director at Gusto

Note all other stakeholders

Who are the other people on your (client) team who are involved in the project and providing approvals? Will they be available to your creative partner for direct questions, input, and collaboration? Having one main point of contact on your team is critical — but at the same time, it can be helpful for everyone to have access to one another as a broader team.

Taking stock of everyone involved also helps you keep an eye on “emerging stakeholders”: new people on the client side who are looped in for input after a project is already underway. New opinions and agendas can derail a project from the original purpose and scope, so get ahead of these surprises by identifying all required participants early on in the process.

With startups, we usually try to make sure we are going as far up the chain as possible. Ideally we want the CEO to be a key stakeholder. A lot of the DNA of the company is in their brain. In a bigger company, the DNA is well articulated downstream. But with a startup having access to the founder/CEO/C-level executive, we can work through any hurdles.

Halli Thorleifsson, Design Director at Ueno, large agency

Transfer knowledge and connect external and internal designers

Make sure that your creative partners’ process works for your internal design team day to day. Share style guides, feedback conventions, and detailed information about the end audience.

Solid knowledge transfer from the client yields the best work from our team. Don’t hold anything back and give us all the info you have.

Adam Weiss, Founder & Exec. Creative Director, Landscape, medium-sized agency

Include all project stakeholders at key inflection points

Project stakeholders on your client team should be involved during project kickoff meetings, key presentations, and approval milestones. This lets you get feedback at the right time from the right people so you can stay within scope and timeline, giving your creative partner the consensus they need to move forward.

In addition, these important moments build trust and make all stakeholders feel like they are a part of the project. A wide range of perspectives improves work quality and helps to unearth needs from collaborators who aren’t decision makers (for example, a developer who will implement designs after handoff).

And, of course, keeping senior executives in the loop prevents them from coming in at the eleventh hour to cut or seriously alter the project — affectionately known as “swoop n’ poop”.

Reserve time and resources for handoff and implementation

Do some mental expectation-setting. Allocate an extra week for refining details and ensuring a smooth handoff. Also ask for permutations of deliverables you might need in the future, in case the contractor isn’t around.

Keep an eye on shifting timelines

If you’re working with a small studio or independent freelancer, shifting timelines can cause resourcing issues. Don’t be surprised if a freelancer is unavailable for last-minute date changes. If your timelines change often, consider putting the vendor on a retainer model where they reserve time for you, or think about working with a studio or agency instead.

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Giving feedback

Learn how to give and receive productive feedback. Have a feedback process and “code of conduct” according to which your team and creative partners will behave.

  • Always select one person on your team — the main point of contact or “feedback champion” — to synthesize and deliver all client feedback so that you’re not sending it in from multiple people.
  • Whenever you review deliverables, start by returning to the original goal to help filter feedback. This also helps avoid scope creep.
  • Write down feedback to make sure it’s all communicated and can be referenced later.
  • Everyone on your team should know where you are in the cycle of revisions, and when it’s last call for final feedback.
  • Sequence your feedback in the correct order (e.g., UX → interaction → content → visuals).
  • Synthesize team feedback so your contractor doesn’t need to resolve conflicting opinions.
  • Translate the feedback of nondesigners into the language of design. For example, if a site feels too “cold” to a stakeholder, what does that mean to a designer? Are they talking about color, or lack of it? Too much whitespace? Lines?
  • Provide timely feedback by baking it into your schedule and internal process. Plan time after presentations to synthesize and swiftly deliver any additional feedback.

One of the biggest struggles I’ve run into with clients is keeping them on schedule. Because it’s only me, I typically take on one or two big projects at a time and hold that project time for my clients.

If a timeline gets pushed out because of delays on the client’s end, there’s potential for it to overlap with other upcoming projects of mine. As much as I like to be flexible, clients need to understand that freelancers aren’t available indefinitely. They should plan accordingly.

Jessica Strelioff, Independent Designer and Creative Director

Troubleshooting when things go wrong

Let’s say you don’t like the work your partner is creating, even after a round or two of feedback. What do you do?

Across the board, service providers and clients say that open, transparent communication and a conversation about what’s not working is almost always the best way to course-correct. Here are some suggestions to help realign when things feel shaky, and some paths forward if the work still isn’t meeting your needs.

Initial course-correction

  • Refer back to written feedback together.
  • Use video calls (instead of email) to troubleshoot and make sure things aren’t lost in translation.
  • Refer back to initial conversations and scope to get aligned.
  • Get all decision makers in a room to discuss feedback, especially if there was a project handoff internally — this also ensures that nothing was lost in translation.

When things still aren’t working

  • Get the two most senior people from each team on the phone to reestablish rapport and get back on track.
  • Put a different designer on the team.
  • Have the external and internal teams work side-by-side.
  • Limit the scope of the project.
  • Get whatever good work you can get out of the vendor, then let other resources take it from there. For example, you might hire an agency to do an entire rebrand, including visual identity, logo, and website. If you love the logo and visuals, but hate the website, you can just keep what you like. Use the logo and visuals as a starting point for someone else to build out the website.
  • Ultimately, if it’s not a fit, agree on the completed scope of work and part ways.
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Make magic happen

When you launch yourself into the search for creative services, a little preparation goes a long way. Before you speak to providers, get internal consensus on what you need. Lean on investors and design colleagues to make introductions and review portfolios. Vet responsibly, and when you find the perfect fit, put guardrails in place to help your relationship succeed.

Because when you pull the right team together, it feels like magic.

It’s a great feeling when you wrap up a project with an amazing client. All of the work that has been designed, workshopped over, specced out, triple checked, and QA’d has been released.

It’s important to realize that the final creative is just part of the work. The other half is celebrating the collaborative process work that has been done behind the scenes.

Adam Ho, Freelance Designer

We hope you find the creative partners to help you realize your vision — over and over again.

Written by Kelsey Aroian and Nathalie Arbel.

Thank you Emily Kramer and Micah Panama for sharing their perspectives and to all the wonderful freelancers, studios, and agencies that helped contribute to this piece: Adam Ho, Jessica Strelioff, Landscape, Math Times Joy, MetaLab, and Ueno.

The artwork for this piece was designed by Ricardo Santos.

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Medium's largest active publication, followed by +720K people. Follow to join our community.

Designer Fund

Written by

We back exceptional founders and empower them with design to improve the world.

The Startup

Medium's largest active publication, followed by +720K people. Follow to join our community.

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