CHALLENGE
"Although we have a pretty big database of people opted in to our mailing list already, it's my personal goal to continue building that," says Meg Bruno, Marketing Director for Boston's alternative lifestyle paper The Weekly Dig.

She has to market to two different demographics -- men aged 18-34 who should read the paper, as well as restaurant and club owners who should advertise in the paper. Both aren't wowed easily.

Local businesses are besieged by ad sales reps from loads of competing papers and sites.

And, although hordes of young men may surf WeeklyDig.com (typically for five and a half minutes per visit), they're fed up with typing info into countless online registration forms. The payoff has to be overwhelmingly great to convince them to hand out their email address yet again.

Bruno's webmaster had naturally positioned an opt-in offer for a newsletter about the site on every single page. But how could she get opt-ins from readers and fans who hadn't clicked on that relentless offer?

She needed an additional, super-compelling opt-in offer to catch those non-responding visitors.

CAMPAIGN
Young men in Boston are likely to be single and, like single men everywhere, many are likely to be a bit shy. So, instead of schmoozing in person, many in this generation like to start flirting by sending the object of their desire a super-witty email that she'll find irresistible.

Yes, but how many of us have that kind of wit at our fingertips, especially on short notice?

That's when Bruno's team had the big idea -- why not offer a personalized break-the-ice email letter service? Web site visitors could enter information about themselves and the one they yearn for in a relationship survey form. (Link to sample below.)

The form asked questions such as "what's your favorite restaurant?" that were equally handy for crafting a personalized letter and for impressing potential sponsors with real-life (aggregated) data.

The form data then automatically posted to a private extranet that a team of freelance writers visited daily. A managing editor sorted through the queries, matching writer to form to get the best results. Generally within 24 hours a newly written letter would go out. (If one writer couldn't make the deadline, the system shifted responsibility to the next writer.) While 24 hours is a long time to wait for an automated letter, it's the perfect length for a personal letter. In fact, if your turn-around speed is incredibly fast, some consumers might doubt the authenticity of that all-critical human element.

The subject line varied slightly depending on whether the sender wanted to be anonymous or not:

Sender Identified: Hey [RECIPIENT], [SENDER] has sent you a message from the Virtual Wingman!

Anonymous Sender: Hey [RECIPIENT], you have a message from the Virtual Wingman!

Once the writer got started, each letter took between one and 15 minutes to craft. (Link below to sample.) Total cost, about $7 per opt-in name including the registration form and personal letter service. It's just a bit higher than the $5 per name many emailers pay for data-heavy co-registrations from name-brand sites.

The system had two key rules to avoid abuse:

Rule #1. Letters would be sent only on behalf of live, confirmed email addresses. "We send a confirmation letter to your email address (to ensure you're really you and not Gary from Accounting punkin' yer ass)."

Rule #2. "We are a virtual wingman, not a virtual stalker. You only get to send one message to each recipient each three-month period."

Rule #3. The privacy policy was clearly spelled out, plus new users had to check a box to indicate they'd read and understood the privacy info.

Rule #4. No hateful messages would be sent, and the writers could decline to send particular messages.



RESULTS
The Virtual Wingman offer launched on WeeklyDig.com this summer. "Our visitors love the hip, smart humor in the greetings," says Bruno. "And, our sales force gains an instant edge in the local market."

60% of Virtual Wingman users are men with an average age of 27. 4% of WeeklyDig.com's monthly site visitors click to the page to learn more about the service. 8% of those who read about the service then fill out the entire (fairly long) form to send out a personalized email message.

About 10% of all users are fakers -- inputting an email that's not their own hoping to "punk" someone. Naturally those letters are not sent.

Useful links related to this article

Creative samples from WeeklyDig's Virtual Wingman campaign: http://www.marketingsherpa.com/weeklydig/study.html

Arriviste Press - the outside company that powers this campaign (including customized registration form and writers for the personalized written replies): http://www.arrivistepress.com

Message Labs -- the email service provider that sends out the letters: http://www.messagelabs.com

Weekly Dig: http://www.weeklydig.com