How to Land a Gig on

Wondering why you can’t land a gig on Don’t worry. You’re not alone. There’s tons of unspoken do’s and don’t’s of how to land a gig that might not seem overly obvious upon first glance.

I won’t lie, starting out is tough. That’s the downside of directory sites like Thumbtack: if you’re a new player in the game with no discernible online presence, you’re basically starting from scratch. With zero reviews to start, it took me an upwards of a month to land my first gig, even though I’ve been a professional face-painter for eleven years.

But, six months after my first gig, more 5-star reviews meant more gigs meant more 5-star reviews meant… you get it.

Here’s a few things I’ve found to be helpful, which, you don’t even have to be a face-painter to make use of:

Be the first to bid. Always.

There’s something psychological about this one, I think. Most of the times when I was able to land a gig, I was the first one to bid. You are your potential client’s first impression to the world of face-painters (or whatever your specialty), and that you were eager enough to respond to them quickly highlights your professionalism. Responding quickly and first makes it seem personal to your potential client. Bidding late or last makes it seem like an afterthought to your client.

This isn’t a secret practice, either. I’ve sent out bids within five minutes of the initial lead only to find that two others had as well. Don’t rush to the point of sloppy mistakes (I’ve accidentally called a client by the wrong name before – whoops!), but make use of Thumbtack’s quote templates to save yourself massive amounts of time. If you don’t mind a bit of interrupted sleep, especially when you’re first starting out, consider turning on the option to receive text messages between 9 p.m. and 8 a.m. – the default setting for this is ‘off’. I landed a gig once when the client posted the request at 1 a.m. and, since I never sleep anyways, I was the first to bid.

Always send a follow-up message.

It doesn’t matter whether you send a follow-up message on or just a follow-up message to a cold pitch you sent, so long as you send a follow-up message. This is non-negotiable. You need to follow up with each and every quote you send. Maybe it’s confirmation bias, but I think it’s just a necessary component of professionalism. Any time I was able to land a gig, I’d sent a follow-up message.

I generally wait until the morning after all the bids have been submitted. There’s no need to be pushy when you follow up, as you can achieve the same effect without seeming aggressive or desperate for business. A polite, “Hi [name]! Have you made any decisions about your event yet? I’m still available and interested for [event]. Please let me know if there are any questions I can answer. Best, [your name]” or something to that effect. Keep it short. You shouldn’t treat the follow-up message like you’re bidding on the job all over again, and this isn’t the time to include important information that you should have put in your original pitch.

Peek at what your colleagues are saying.

Don’t create a fake lead. Not only is that a dick move and a clear violation of the site’s Terms of Service, but it wastes the freelancers’ time and money since they have to pay to bid on jobs (not to mention, it only strengthens the idea that Thumbtack is full of scams). Instead, scour forums or subreddits in your specialty; perhaps ask others to post their gig-winning pitches (it helps if you ask someone whom you are not in direct competition with – say, someone from a different time zone altogether).

You may think that your pitch is perfect, but there’s always something to improve upon. For instance, after peeking at a fellow face-painter’s pitch, I added a few lines about how I use non-toxic, hypoallergenic paints and I sanitize my brushes. It’s standard practice and not something that I particularly cared about, but it’s something my clients cared about. Plus, adding a sentence or to about it shows that I care about the quality of products I use and, thus, the quality of my service.

You never know what will appeal to whom, and in the end, it may just help you land a gig.

Offer a freebie

Another little tidbit I gleaned from peeking at others’ pitches: offer something extra. I don’t mean giving away services for free (and in fact, don’t do that), but just a little extra something that makes you stand out.

When a potential client fills out the canned form for quotes on Thumbtack, they already know that they’ll receive up to five competitive quotes. Telling them that you’re the best face-painter around is most likely what your competitors are saying. You have to stand out and create value, and offering something extra does just that. Plus, it gives your client reason to believe that you really are the best, seeing as how you’re willing to go above and beyond what is necessary.

Or, if nothing else, people really love free shit.

Ideas for my fellow face-painters: one lady I talked to would offer personalized name graphics for whomever’s birthday. It was something that only took her ten minutes to make in Photoshop and then print. Other ideas could be including in your service kit things like henna, airbrushing, rhinestone ‘bling’, special FX makeup, etc. Get creative. The sky’s the limit!


Now, wish that it were true, there’s no set of words that when put in the right order will guarantee you a gig. If that were the case, I’d be making millions already selling that secret. Instead, take the time to perfect your pitch, incorporate some of these tips, and have patience. You’ll conquer the world in no time.

Did I miss anything? Got any other tips for your fellow side-hustlers when it comes to landing gigs on Thumbtack? Leave them in a comment below!

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