TwineAsk any manager who works with freelancers what their biggest fear is, and it’s rarely quality. It’s availability. The animator who nailed your last three launches suddenly “isn’t taking new projects until spring.” The developer who knew your codebase cold has gone quiet.
That’s the blended-workforce reality. Upwork’s Freelance Forward research found that 64 million Americans, 38 percent of the US workforce, did freelance work in 2023, contributing $1.27 trillion to the economy. The best of them are not waiting by the phone. They run a portfolio of clients, and when their calendar fills, somebody’s projects get deprioritized. Your job is to make sure they’re not yours.
Employees get onboarding, reviews, promotions, and employee recognition programs. Freelancers often get a purchase order and, if they’re lucky, a “thanks!” in Slack. Yet some of the most effective ways to become a client they want to work with again cost very little.
1. Pay fast. It’s hygiene, not a gift
Before any talk of appreciation, pay invoices quickly. Late and missing payments are endemic in freelance life. A Freelancers Union survey found more than 60 percent of New York freelancers reported not being paid for work they performed at some point.
Prompt payment is the contractual baseline. But a client who pays reliably and without chasing is easier to prioritize than one who turns every invoice into another piece of work.
2. Give credit where the world can see it
Freelancers live on proof of work. Credit them by name in the launch post. Write the LinkedIn recommendation without being asked. Offer a specific, results-oriented testimonial they can quote: “cut our render time 40 percent” beats “great to work with.”
Where NDAs allow, approve portfolio use in writing. That permission helps them win their next project and costs you an email.
3. Refer them, even when it feels risky
Recommending your best freelancer to a peer can feel like giving away a competitive edge. But freelancers build their businesses through repeat clients and recommendations. Sending good work their way shows that you value the relationship beyond what they can do for you.
It may also make yours a relationship worth protecting when their calendar fills.
4. Mark exceptional work with an actual thank-you gift
When a freelancer pulls off a weekend save or wraps a monster project, a thoughtful gesture can carry more weight precisely because non-employees rarely receive one.
There is evidence that unsolicited gifts can create goodwill through reciprocity. In a large field experiment published in Econometrica, enclosing a small gift with a request increased responses by 17 percent, while a larger gift increased them by 75 percent. The study wasn’t about freelancers, so it shouldn’t be read as a measure of contractor retention, but it helps explain why an unexpected thank-you can feel different from compensation someone has already earned.
For distributed talent, it can be practical to send digital gift cards in bulk because they can be delivered without arranging physical shipping and give freelancers more choice over what they receive. This works especially well for remote or international contractors, where sending a physical thank-you gift may be harder to manage. A personal note naming the specific contribution makes the gesture feel like a thank-you rather than an automated reward.
Keep one boundary clear: a gift is appreciation layered on top of a paid engagement. It should never replace contracted fees or be presented as part of the freelancer’s rate. Keep compensation in the contract and appreciation outside it.
Businesses should also keep accurate records of payments and other compensation provided to contractors. Depending on the circumstances, amounts may contribute to payments reportable on forms such as the IRS 1099-NEC, so the tax treatment of a particular gift or incentive should be checked rather than assumed.
5. Treat them like insiders between projects
A freelancer may not be an employee, but that doesn’t mean every interaction has to feel transactional. Give them a heads-up about next quarter’s likely projects so they can hold time. Invite them to an optional team demo. Ask their opinion on a brief before it’s final.
Those small signals make it easier to build continuity with people who otherwise move from client to client. More importantly, they give good freelancers something money alone cannot guarantee: a working relationship worth making room for.
Become the client they want to come back to
Replacing a proven freelancer means sourcing, vetting and briefing someone new, then waiting while they learn how your team works. Keeping a good one is usually much simpler.
Your best freelancers have choices about which clients make next quarter’s calendar. Pay them promptly, help them build their reputation and show appreciation when they do exceptional work. Give them reasons to choose yours.
Common questions
Can you send gift cards to freelancers and 1099 contractors?
Yes. Businesses can send gift cards to freelancers and 1099 contractors, but they should keep accurate records of the value provided and check how it should be treated for tax-reporting purposes. Gift cards should be an additional gesture of appreciation, not a substitute for contracted payment.
What is the best way to send gift cards to a remote or international team?
A practical option is to use a platform that can send digital gift cards in bulk to remote or international recipients. This avoids the need to collect shipping addresses, gives freelancers more choice over what they receive, and makes it easier for businesses to manage rewards across different locations. Businesses should still confirm country availability and keep records for tax-reporting purposes.
What are the best platforms for sending gifts to freelancers and contractors?
The right platform depends on what you want to send.
- Giftogram is best for companies that want to send flexible digital rewards to freelancers at scale, particularly across remote and international teams, with a choice of gift cards or prepaid Visa and Mastercard cards.
- Snappy is best for companies that want freelancers to choose from physical gifts, experiences, or branded merchandise.
- Goody combines physical gifting with gift card options.
- Sendoso is designed more broadly around corporate gifting, direct mail, and sales and customer engagement.
Are gift cards a good reward for contractors?
They can be, particularly when recipient choice is built in. For a distributed or international team, digital delivery also avoids the address collection and shipping involved with physical gifts. Gift cards work best as a genuine thank-you for a specific contribution rather than as a replacement for fees the contractor has already earned.
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