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

I wanted to make sure that getting in touch with me would be as easy as possible for the recipient. The only CTA for a Penny Poke recipient was to wait for me to reach out to them and in the meantime, look at my portfolio.

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.

What’s the response been like so far?
The response has been incredible.

"Nine recruiters and creative directors from the 16 agencies I targeted have now responded to my follow-up email saying they love the idea and/or the agency is reviewing my portfolio."
Connie Chweh

I started Penny Poking people on my birthday, Sept. 4. I wanted to ride on some birthday luck as this tends to be a thing in my life. On my birthday last year, I was selected to be on The Price is Right, LOL. I sent out 35 pennies and had 32 visits on my site, ROI on point. Some of those visits were from me, though, from testing and such, so maybe 29 visits. On Sept. 5, I sent out seven more pennies and had 24 visits. Some of those probably being residuals of the previous day.

As of now, nine recruiters and creative directors from the 16 agencies I targeted have now responded to my follow-up email saying they love the idea and/or the agency is reviewing my portfolio and/or they want to meet me!

Getting contacted by a stranger on Venmo feels pretty odd—a bit like a random AirDrop. Did you worry about anyone being creeped out?
I definitely worried about this, but it just made me more thoughtful in what the overall user experience would be like. Since Venmo captions are limited to 280 characters, I had to be tactful about what the initial messaging was to the Penny Poke receiver in order to spark more curiosity than fear and skepticism. Then I had to ensure that the copy and art direction for the Penny Poke landing page was fun and inviting to get them to hear me out and click through to my portfolio.

Tell us a bit more about yourself. What kind of job and employer are you looking for?
I’m an art director who appreciates a good, simple idea, beautifully crafted. I’m also a pretty curious person and like doing things the “wrong” way. To be honest, I kind of like getting in trouble from time to time. It just makes life more interesting.

I’m moving to New York without a job or a place to live and sending out Penny Pokes to random people on Venmo, that’s as close to a plan as I have. But I’m very hopeful, and I have a feeling that things will work out. They always do.

Right now is a pivotal time in my career, and I believe the next agency I’m at will really shape me as an art director. The most important thing I’m looking for at my next shop is good people. I want to be surrounded by diverse, smart and just down-to-earth people whom I can grow from and who will make work feel like a second home.

I’m coming from FCB West, where I was with amazing people every day— this is something I’ll miss very much. I’m also looking for an agency that has strong female leadership—shoutout to my CCO at FCB West, Karin Osanger-Birch—is digitally savvy and isn’t afraid of breaking some rules for a crazy idea.

Not much to ask for, right?

You can learn more about Connie Chweh on her portfolio site,

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