How a Job-Hunting Art Director Used Venmo to Get Recruiters’ Attention

56% of Connie Chweh's targeted agencies have responded

Connie Chweh sits behind an Apple laptop, with a stack of cookies and a mug.
Art director Connie Chweh took the idea of the 'Penny Poke' on payment app Venmo and turned it into a modern cold-calling tool. Connie Chweh
Headshot of David Griner

Is there any place harder to get noticed than in a top-tier recruiter’s inbox?

Often the secret is to sidestep the inbox altogether, but sometimes a job-hunting strategy that’s too far afield can seem gimmicky to the point where it overshadows your actual workplace talents.

Agency art director Connie Chweh, who’s hunting a new employer to help facilitate her move from San Francisco to New York, seems to have found a strategy that—for now—hasn’t been overly exploited by job seekers.

She’s been sending “Penny Pokes” to recruiters and creative directors via payment app Venmo, which allows you to send messages to users—if you send them some money too. You also have to guess the right user name for the right person.

Recipients get a Venmo notification that they’ve received one cent from Chweh, along with a note linking to her Penny Poke landing page.

Here’s how it looks:

So far, she says she’s heard back from recruiters or creative directors at nine of the 16 New York agencies she’s targeted. That’s a 56% rate, not counting the dozens of anonymous clicks she’s gotten to her landing page.

We caught up with Chweh to learn more about her strategy, how it came about and how recruiters are responding:

Adweek: How did you come up with the Penny Poke idea?
Connie Chweh: The Penny Poke idea coalesced from actually a few points in my life:

About seven years ago, I received my first Penny Poke from a friend whom I hadn’t spoken to in a while. I thought it was such a cool and unique way to get in touch with a long lost friend, and it definitely planted a seed in my subconscious.

Last spring, I was really inspired by the virality of World Record Egg, so I attempted to launch a project called “The Longest Penny.” I wanted to see how far a digital penny could travel on Venmo. My thinking: If I sent a penny to a friend on Venmo and prompted them to send that penny to another friend and so on, perhaps we could create the longest penny in digital history! Mwahahaha!

“The Longest Penny” project flopped (the penny I sent only traveled to 2 degrees of separation), but I took away a few learnings:
• Penny Poking is an active phenomenon on Venmo.
• People are very skeptical on the platform since it’s a payment app.
• There is a 280 character limit for Venmo captions.
• You’re not able to copy/paste Venmo captions.
• But you are able to add tap-through URLs.

Since this past summer, I’ve been cold-emailing recruiters and creative directors in NY, and wow the response rate has been close to 0%. LOL. It was discouraging, of course, but it simultaneously motivated me to think of a more clever, fun way in.

And so came my “Penny Poke” idea: What if I Penny Poked recruiters and creative directors on Venmo to get their attention?

How did you decide whom to Penny Poke? How wide of a net did you cast?
I Penny Poked recruiters and creative directors from agencies that I want to work at. These are agencies that I admire for their ideas, craft, and/or reputation. But actually, I could only Penny Poke people with unique or somewhat unique names—i.e. not super common names, otherwise I would get a plethora or results for names like “John Smith.”

I cast a pretty wide net since I wasn’t sure how people would respond to the gesture; I think it’s a love it or hate it kinda idea. Plus, not everyone has their notifications turned on for Venmo. In total, I’ve Penny-Poked 42 people— one of those people being David Droga—got to go big! Hopefully, that was actually him and not some other David Droga.

How do you follow up once you’ve “poked” them on Venmo? Do you ask to move the conversation to email, etc?
So the Penny Poke project comes in 3 phases: digital, direct e-mail and activation:

• Phase 1 (Digital): Penny Poke on Venmo
• Phase 2 (Direct E-mail): Follow up with Penny Poke recipient via email to let them know who I am, what I’m doing and to schedule a coffee meetup with them.
• Phase 3 (Activation): Get coffee with me!

"It's kind of hilarious to me that my brain thinks like this and that it's actually fun for me, but hey, this is the kind of thinking I'll bring to your agency if you hire me."
Connie Chweh

@griner David Griner is creative and innovation editor at Adweek and host of Adweek's podcast, "Yeah, That's Probably an Ad."