To help get businesses off the ground, many start-ups hire freelancers with specific skill sets (app developers, web designers, content writers etc.) for a short period of time.

We really wanted to understand the process of hiring freelancers from the perspective of a startup. What challenges do they face? What could freelancers do better? How can startups and freelancers work together more harmoniously to support each other? To find out, we spoke to three startups, Petal, 1001 Stories and Big 7 Travel, who told us about their experiences of employing freelancers.

Petal is an app that helps people build a healthy relationship with food, 1001 Stories is a fashion brand that produces stunning statement shoes in a very ethical way and Big 7 Travel is a go-to resource when it comes to discovering new destinations worldwide. 


How was your experience working with freelancers?

Aidana Orynbassar is the founder of Petal. Since starting her business, she has had two experiences of hiring freelancers – one positive and one negative.

Regarding her positive experience, Aidana explained “We hired a freelance graphic designer, who has helped us with branding. It was someone we knew before and it was easy to communicate with them and convey our vision.” 

Unfortunately, however, Aidana’s negative experience involved a freelancer that she hired from a well-known marketplace job site. Aidana told us that the jobsite she used, Fiverr, made it difficult to communicate and work effectively with the freelancer in question.

“We found that not knowing the freelancer as a person and not being able to communicate outside of the Fiverr platform, made it difficult to show our perspective to the freelancer.” 

Sarah Clayton-Lea is Co-Founder of Big 7 Travel, a company that relies quite heavily on freelancers to create content about travel destinations across the globe. She has hired numerous freelancers to date, including content writers and tech and design specialists.  

Overall, Sarah’s had positive experiences with the freelancers she’s taken on, so much so that some have transitioned to full-time staff.

“We have had a really great experience overall with freelancers and hired two writers full time after a few months of them freelancing for us,” she said.

However, Sarah mentioned that it took some time to find suitable freelancers at the start.

“It was difficult at the start to find suitable freelancers for content - we posted job ads on several Facebook groups as well as contacting freelance writers from other media brands that we felt would work well for us,” she said.

Tereza Pigova is the Co-Founder of 1001 Stories.

Tereza has mainly used freelancers for graphic design, web development, and photography. Overall, she has had mixed experiences while working with freelancers, saying that “Some experiences were better than others.”

She shared one of her positive experiences with us, explaining that “We had an amazing experience with a freelance developer who helped create our company website. We found this individual through a common connection and knew that he would deliver a great job, which he did.” 


What are the advantages of working with freelancers?

In Petal’s case, Aidana pointed out a range of advantages associated with using freelancers including “cost-effectiveness, a set of specialist skills, and devotion to a project if they like it”.

Sarah and Tereza also shared some of the advantages of working with freelancers.

As they operate within tight budgets, both women highlighted the fact that hiring freelancers is a good alternative to taking on full-time staff.


“As a start-up, we don't have the same freedom as well-established companies have when it comes to making long term hires, as we still have to be quite scrappy. So, freelancers are perfect as we can assign work as and when we need to, without being tied to long contracts,” Sarah explained.


Sharing Sarah’s point of view, Tereza made the point that “Hiring freelancers gives us the flexibility to only pay for what we need in a given moment of time”.

Finally, in order to bring a start-up brand to life, founders understandably want to work with a range of creatives who can bring different ideas to the table.

Employing freelancers has allowed Tereza and her co-founder to do this with their brand 1001 Stories, as she told us that it gives them “the freedom to choose from a variety of talented individuals rather than just always work with one person”.

 girl on chair typing on a laptop

What are the disadvantages?

While the founders had a lot of positive things to say about their experiences working with freelancers, there were a few things that bothered them from time to time.

For example, Aidana was wary of some freelancers prioritising other company’s projects over hers.


“They might be more loyal to another project instead of yours and have no commitment to the company’s mission,” she said.

Furthermore, Tereza felt that some freelancers don’t take the time to properly understand a company’s brand and vision, which is key to effectively portraying the brand in their work.

“Fashion brands have a very strong sense of identity and very well-defined brand values. It is not always easy to find the right freelancer who will understand and be able to portray the brand in the right way,” Tereza said.

Another disadvantage raised by the founders, was that it can be difficult to get a freelancer to fully invest into the community that employers often try to create among their employees, in an effort to help them feel part of a cross company team. 

For example, Sarah told us that it can be difficult to get that ‘team spirit feeling” from a freelancer if they are only working with the company for a short period of time. However, she said that hiring “the same freelancers on a regular basis” and inviting them to partake in activities like “group video calls” can help them to feel like part of the team.


What are the learnings from your experiences working with freelancers?

We asked the founders if, as employers, they would do anything differently the next time they manage and hire freelancers.

Both Sarah and Aidana emphasised the importance of ensuring that the freelancer has a clear understanding of their companies and their respective missions from the outset.

Sarah has developed an “intro pack for the brand” to ensure that freelancers who work with Big 7 Travel have a clear understanding of what the brand is all about from the get go.

“I learnt over time to have a sort of intro pack for the brand which briefly explained what it is and what we're trying to do, as well as a style guide that includes tone of voice. It helps to give a very, very clear brief,” Sarah said.

Similarly, Aidana said that she will take the time to ensure that any future freelancers she works with fully comprehend what her brand is all about.

“I would double-check that they understand the company’s mission and goals and are actually committed to them,” she told us.

Finally, the founders have learned that clarity is key when it comes to communicating with freelancers. 

Ensuring that the role and work required, the expected outcomes and the deadlines are communicated clearly from the beginning, is something that all three founders highlighted.

Sarah emphasised the need to ensure that the “deadline is clear” when working with freelancers. Similarly, Aidana said that she “would be extra clear with what I want the outcome to be” when working with freelancers in future.

Tereza explained that clarity on things like the role and project in question are key to ensuring that money and time are not wasted.

“Having a very clear role and project description is crucial. Lack of clarity leads to undesired results and is a waste of time and money on both sides of the table,” Tereza explained.

 Woman on laptop reading

Any advice for freelancers?

Ask questions, understand what the company is all about, make sure you have the right skill sets for the job and consider the big picture. Yes, it’s important to focus on the task at hand but also understand the context in which the project will impact the client’s company. 

Sarah of Big 7 Travel and Aidana of Petal emphasised how important it is for freelancers to ask questions.

“Don't be afraid to ask questions or ask for help if needed. Just because they're not a full time member of staff does not mean that companies aren't there to help them settle into the job,” Sarah explained.

Aidana shared this view, as she emphasised that “Freelancers should feel free to ask as many questions about the company and the task as possible.”

The second piece of advice that the start-up founders had for freelancers was that freelancers must make the effort to understand the company, beyond the task at hand.

Freelancers must invest time into learning about the startup’s missions, values and culture in order to ensure that their work is well-informed.

“I would be happy to see that the freelancer is trying to understand the mission, the meaning behind the tasks, and the culture of the company,” Aidana said.

Finally, freelancers should make sure that they have the right skill sets to complete a job before they put themselves forward for it.

This is a pretty obvious point but not one that all freelancers adhere to unfortunately.

1001 Stories Co-Founder, Tereza, said that “There were times when we were clearly talking to the wrong person as he/she did not have the right skill set. Sometimes you don’t find out until much later that the collaboration was deemed to fail from the very start.”

If you apply for a job you aren’t qualified to do, your work won’t be up to scratch and you’ll let the client down.

In short, if you don’t have the skill set required, don’t apply for the job.


If you’re a start-up planning to hire freelancers, I hope the insights shared by start-up founders Sarah, Aidana and Tereza offer some help.

If you’re a freelancer, the experiences shared by the founders in this article should give you a good idea of best practice when working on a job with both start-ups and established companies.

If you’d like to speak to us about growing your business using freelancers, get in touch with us here. 

You can check out Big 7 Travel here, 1001 Stories here and Petal here.