Pointers for Planning a Holiday Celebration with Colleagues

2 minute read

If you’re among the 44 percent of small business owners who will be throwing a holiday party this season (as a recent American Express OPEN survey predicts), Jayna Cooke has some advice for you.

She’s the CEO of EVENTup, a Chicago-based online marketplace that pairs party planners with great venues. Cooke got her entrepreneurial start as one of Groupon’s first employees, and this year, backed by the same venture capital team that backed Groupon, she bought the 7-year-old VRBO for events from its California creators. She quickly set out to scale its technology and monetize the service.

“Venues pay us a listing fee to be hosted on our site, and we return page views and quote requests,” she says. Though wedding planners and other individuals search EVENTup, Cooke says most users are companies looking for the perfect space for off-site gatherings or photo shoots. EVENTup offers more than 10,000 venues in 300 U.S. markets. Spaces include art galleries, airplane hangars, warehouses, lofts, rooftops, carriage houses, dance studios, fabulous homes, and boats, as well as the traditional restaurants, banquet halls, and country clubs.

Few small businesses have big budgets for holiday celebrations: American Express OPEN says they’ll spend an average $902 per party this year. But even a New York City small business could host a gathering within that budget in a dance studio or hotel mezzanine: both are listed on EVENTup for rent starting at $250.

Here are Cooke’s tips for doing your holiday celebration right.

  • Plan your event around an activity or a theme. Cooking lessons, a sushi making course, an around-the-world menu, or a “12 cocktails of Christmas” are all ideas for going beyond just decorating for the holidays.
  • Bring in entertainment to make it more fun and exciting. It doesn’t have to be a big headliner: Chicago hosts have hired a violinist who plays hip hop. At Groupon, Cooke says a high school band played for a party.
  • Keep the cheerful mood going all year by providing people a way to remember the event. Rent a photobooth and send your team home with photostrips from the night.
  • “Account for the +1s,” Cooke says. It’s nice to invite your colleagues’ significant others to join the holiday party.
  • Invite the contractors. On a tight budget, this can be a tough call if your contractors work in another city. But Cooke says a rule of thumb is that if you’re spending as much as on a contractor as you are on a full-time employee, then treat them like one and invite them to the company party.
  • If you do it on a weekend, staff can let loose more. Thursday, Friday, and Saturday are best.
  • And, of course, Cooke says one of best ways to ensure a successful party is to “pick a really cool space.” Resist returning to the same banquet hall you’ve visited for the past four years, she says. “Think outside of the box: Airplane hangars, wide open spaces, and boats are always great. In Chicago, New York, and Los Angeles, you can do a city tour and have dinner and drinks and entertainment.”

In early November, Cooke had yet to plan EVENTup’s holiday party. “We are having one, we just haven’t picked a location yet. It’s definitely not too late.”