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Revenue Enablement

Enablement Spotlight: Lessons Learned From WorkRamp’s In-Person Company Kickoff

Each month, Stephanie Middaugh, Director of Enablement at WorkRamp, shares her expertise, from fresh ideas on new enablement strategies to actionable tips to implement at your organization. In this month’s post, Stephanie shares strategies for a successful in-person company event and lessons learned from this quarter’s Workramp Company kickoff.

We just got back from a two-day, in-person WorkRamp Company Kickoff (CKO) in Newport Beach, California—and it was a huge success! 

About 160 people attended—a fantastic turnout for a company of 175 employees. 

Leading up to the event, a lot of planning took place, especially since this would be our first in-person event before the pandemic. WorkRamp is a 100 percent remote organization; around 75 percent of our employees had never met face-to-face! So it was amazing to get together and interact with everyone in 3D. 

Before the event, I worked closely with our CEO to determine the overall theme and what we hoped to achieve. We weren’t rolling out a new methodology or showcasing new products—the event was about bonding and team building. We’ve grown fast following our Series C funding round in March. My challenge was getting people out of their comfort zones to network and have fun—not an easy feat coming out of a pandemic that kept many people isolated for extended periods.

After extensive deliberation, we decided on a few activities we felt would do the trick—and they did! Here’s what happened:

We created superheroes

in-person company kickoff

We partnered with a non-profit organization, Together We Rise from Orange County, California, for a Build-a-Superhero-Box activity. The boxes are delivered to foster children around the L.A. area. Knowing from prior experience just how meaningful these events can be to employees and the non-profit, I knew this was one pillar that couldn’t be skipped. Working together for a good cause is inspirational and a great way to transcend our differences. It felt great to give back to the community, and we received so many positive comments in our survey about this activity

We mixed things up

To break the ice and get people mingling and interacting, we pulled a “Table Swap.” Between executive presentations, we asked everyone to stand up and move to another table. This simple activity got people talking to other folks from different teams and departments across the organization. Pro tip: Do this activity 2 to 3 times max, so people can settle in and get to know each other a little before changing seats again.

We played “Rock, Paper, Scissors”

This fun activity was a colleague’s brainstorm. We asked people to turn to someone next to them and play “Rock, Paper, Scissors.” The winner had to go find another winner and play against them. As people dropped out, they began cheering the remaining winners on until only two were left. We brought them on stage for the final round. People were hooting and shouting and jumping up and down-–they really got into it!

We had team sessions

 Rather than dictating every activity for CKO attendees, we allowed team leaders to choose activities for their teams during a block of time and dig into whatever they felt would be most beneficial. whether team bonding, brainstorming, training, or some other activity. This allowed remote teams to interact and bond together as a group, which can help them feel more connected to each other once they’re back in their home offices. 

We partied

The tried-and-true evening cocktail hour is always a big hit—and the one at our CKO was no exception. We also hosted larger department dinners so employees from each team could get to know their immediate co-workers better as well as co-workers across other teams that they might not always interact with. It’s essential to provide time and space for people to experience other departments and teams, so when you throw an in-person company event, make time for both types of gatherings.

We made time for downtime

Let’s face it— we’ve been antisocial for over two years now, and extended periods of social interaction are draining for many of us. That’s why we made sure to plan plenty of downtime. It’s critical to schedule long breaks—ours were two hours—for people to regroup, relax and re-energize before proceeding to the next activity or event. That way, when they attend the presentations and team sessions, they’re present and can participate and contribute to their fullest potential.

Given the current events, WorkRamp’s remote culture, and few of us have ever met in person; I wasn’t sure how our CKO would go. But, thanks to everyone coming together to plan fun, interactive activities, it was a huge success. 

We’ve received comments from many employees saying they feel more connected to the organization and the people within it than ever—which is a great recipe for long-term success.

We’d love to hear your ideas for making in-person events productive and fun. Send me a message on LinkedIn to share your thoughts and keep the conversation going! 

 

 

 

Stephanie Middaugh

Stephanie Middaugh is the Director of Enablement at WorkRamp. Stephanie is a fearless and spunky sales enablement professional with more than 11 years in revenue operation and enablement functions. Data and results-driven with a desire to break the mold of what enablement and training typically look like, she isn’t afraid to try new things and has a track record of building impact-making and scalable programs and training at startups that have led to successful IPOs and acquisitions during her tenure. Stephanie also has a strong passion for professional community building and is a prominent voice on LinkedIn. She co-founded an Enablement Slack channel for professionals to network, share best practices, and get advice from colleagues across industries and the world.

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