The DC company that will plan your weekend for you

A member of Ask Jenna and her family on a horseback riding experience. Photo courtesy of Ask Jenna.

If you asked her, Jenna wouldn’t call herself an event planner or a concierge. She’s just the person who’s always on the outside, the face of a new DC service – Ask Jenna – who will plan and personalize your days and evenings.

For $ 129 per month, Ask Jenna hosts outings that include sports games, concerts, outdoor recreation, Michelin-starred meals, and other activities for its members. Customers can choose from a variety of options based on preferences they indicate in their membership profiles and a half hour call with an “experienced architect”. They also get Notes from Jenna — a guide on how to optimize their experience.

It’s a lot of work for a woman who isn’t even real.

“Jenna” is actually Janece Kleban and Jenny Shtipelman’s concoction, a combination of their names and the avatar behind their service. The duo went from good friends to business partners. “You ask Jenna, and she’ll take care of it for you,” said Shtipelman.

The idea came to Kleban, originally from DC, after arranging a date with her husband. “I ended up marrying a guy who can’t plan anything,” Kleban says, “Anything. He suggested that she turn her ability to organize fun days into a full-time job.

She stepped down as director of development at Goodwill of Greater Washington, contacted Shtipelman, senior vice president of the National Capital Bank of Washington, and the two opened the member service in 2019.

Ask member Jenna and her son in a virtual reality experience. Photo courtesy of Ask Jenna.

Months later, Ask Jenna found herself in a pandemic-stricken town with many locals reluctant to go out as before. Kleban says residents’ varying levels of comfort have forced them to think creatively and turn to more outdoor and virtual experiences. Today, Kleban and Shtipelman are planning outings for around fifty members and their guests. “Our sweet spot are people in their mid-thirties to mid-fifties,” says Kleban, “people who are entrepreneurs, people who are executives or people in leadership positions”.

Kleban says the company will hire full-time staff in 2022 as it rolls out an SMS platform to keep members up to date with their experiences. Eventually, they hope to extend the concept to other cities.

“The current goal is to really optimize the way we use this technology and to optimize the business relationships that [Shtipelman] brings, ”says Kleban.

Zach Bright

Zach joined the Washingtonian in October 2021. In the past, he has written for The Colorado Sun, The Nevada Independent, and SRQ Magazine.


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