Finding freelancer nirvana

Being freelance is in fashion as we hurtle into an evermore decentralised world. How do you get the best out of talent external to your organisation? Dan Salkey, Co-founder of Growth agency °Small World, offers his thoughts.


  • Good freelancers are like gold dust to startup founders looking to grow fast
  • Pay them as soon as jobs are done, if not partially in advance
  • Treat them like part of the team but think about what benefits may be bespoke to them
  • Make sure there’s a clear method of communication on projects
  • Weigh up whether to use project fees or longer contracts
  • Constantly scout the best freelancers like you would full-time talent

The freelancer was once a trusted role of noble talent, first attributed to Sir Walter Scott (1771–1832) in his book Ivanhoe, to describe a "medieval mercenary warrior".

Rather than the knight being free of charge, this term indicated that they were not sworn to any Lord's services. Far from being seen as a simple sellsword, the freelancer was one of the most revered and in-demand talents in all the lands.

Today, these noble knights have traded in their shield and lance for a Wacom tablet and pen but they aren’t to be any less revered than before. Of all the businesses in the land, high-growth startups are the ones that rely on them the most.

Freelancers are on-demand, specialist talent. They fill gaps where they are most needed, helping startups continue to grow in ways they might otherwise struggle with if they were solely reliant on full-time employees.

I run an agency that adapts to fit ambitious startups' stages of growth. We do so through a decentralised model, managing remote teams of the very best freelance strategic and creative talent to offer a flexible, efficient, and affordable service. Given my position and oversight of the freelancing landscape, I thought I’d give you some of our top tips for finding, retaining, and getting the most out of freelancers so you can be the Sir William Scott of Silicon Valley.  

Pay Day, Pay Day!

The first tip is so simple, yet so many businesses neglect it. Pay. Your. Freelancers. On. Time. They should never have to chase an invoice. In fact, you should proactively ask for invoices and, where possible, pay half up front.

This cannot be understated. The freelancers we work with cite late payments as the number one reason they wouldn’t work with a client again or would prioritise other job opportunities. In a world dominated by the demand for rapid growth, you simply can’t afford to have the best freelancers unavailable to you. I can understand that longer payment terms when your business is a technophobic multinational beast with several layers of procurement may be unavoidable, but in the fast-paced startup world, there isn’t much excuse.

Treat Em’ Sweet, Keep Em’ Keen

The best freelance talent has never been more in demand. Similar to how VCs now have to offer more than just capital to attract the best startups, the same can be said for freelancers.

This means making them feel a part of your startup’s culture. This is particularly important if they are on an extended contract. If they’re on short-term projects, look to freelancer communities for inspiration on the type of support and benefits that are appealing for gig workers.

This also means keeping them engaged outside of contracts with content that develops and supports them. Similar to how a VC may have a Head of Platform or Community. Is there a part of your content stream and people strategy that can be tailored towards freelancers? Freelancers should not be seen as disposable. They should rather be seen as talent to be nurtured, with an eye to long-term relationships rather than short-term ones - just like your full-time staff.

The likes of Sarah Cross’s Freelancer Magazine, Albert de Symons Azis-Clauson, Underpinned, and Matthew Knight’s are invaluable places to find tools and content relevant to freelancers.

A freelancer with a high opinion of your startup is your greatest ally because they’re fantastic networkers – they have to be. Not only does this mean you then get to keep the best freelancing talent, but you become known for the right reasons amongst other freelance talent.

Luckily for °Small World, our culture is built around freelancers, which means our benefits and initiatives are too, whether that’s adding extra cash to an invoice for local freelancers to join us for a drink when jobs are finished, or our Slack group, a place for current, former and future °Small World freelancers to speak about work, life or anything in between.


We live in the generation defined by communication - we’ve got hundreds of ways of interacting with each other just on our phones alone - but ironically we’ve never been worse at doing it.

When you’re working with freelancers, and particularly freelancers who work remotely, communication is key. They won’t inherently know how your startup works and which tools you like to use for feedback or collaboration.

That means you’ve got two options; 1) Have a detailed breakdown of your feedback processes, client contacts, and tech stacks you use. (You’d then take new freelancers through this - like a freelancer bible) or 2) Work more flexibly meaning you have a kick-off call with your freelancer in which you agree on loose parameters like the number of feedback rounds you’ll have and which tools you both like to use for collaboration.

At °Small World we swear by Google Workspace tools if you want cost-effective solutions for feedback. When it comes to day-to-day communication it’s Slack all day. Honorable mentions to Airtable, Notion, and Figma.

To Project Fee or Not To Project Fee

Another key decision when it comes to working with freelancers is deciding whether you’re going to pay a project fee or a rolling contract. The gig work landscape has changed dramatically within professional services in the last year alone. Many freelancers have gone from taking ‘perma-lance’ roles (long-term fixed contracts with one employer) to taking a collection of shorter more diverse project-based roles which they can work on simultaneously. Part of that has been sparked by IR35 regulations but also the new ability to work remotely efficiently.

If you have a project that has clear time-sensitive deliverables, a project fee makes most sense e.g. design assets, content creation, a web build. If it’s a job that you think will evolve as you’re working and underpins a function of the business (e.g. the product itself), then a contract makes sense.

°Small World always uses project fees where possible. It’s easier for us to calculate a flat fee for a clear set of deliverables but it’s also beneficial to the best freelancers. Whilst we use a day rate to work out our project fees, the best freelancers will often be able to deliver in a shorter space of time meaning they get more bang for their buck and our clients are pleasantly surprised. Win, Win, Win.

Add Freelance Scout To Your CV

The final bit of advice relates to finding freelancers. There has never been a larger pool of fantastic freelance talent and it’s only set to grow - 92% of professionals think now is a good time to enter the gig economy.

Finding the best talent can therefore be like finding a needle in a haystack. It’s not as simple as a quick google search or a post on Linkedin.

Dedicate resources to building, maintaining, and engaging a list of the best freelancers just like you would when looking to hire full-time talent. This could be a task your Head of People/Talent takes on. For us, it’s a role we want to hire for in the near future called a ‘Head of Freelance’.

Our secret sauce is our fantastic community of freelancers and our knowledge of how best to manage them to achieve efficient growth for startups. So it only makes sense that we have someone dedicated to nurturing the best freelance talent and championing them even when they’re not working for us.

Summing Up

These 5 tips are by no means an exhaustive list. I’d love to know what else you’ve learned working with freelancers so please feel free to drop me a message on Linkedin or give me an email. If you have a project that you're not sure whether to hire full-time, freelance, or get an agency for, I'm more than happy to give some advice.

Dan Salkey is the Co-Founder of °Small World, an on-demand marketing service that scales with your startup as you grow. They’re helping ambitious brands by re-thinking how an agency should work. They help grow businesses from Seed to Series C, building your brand and driving performance along the way.

Reach Dan at or Linkedin.

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