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Sales Enablement

Enablement Spotlight: 6 Ways to Create an Inspiring 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 discusses how she was able to throw a company-wide kickoff with lessons learned. 

To get ready for this year, we decided to do something BIG and different at WorkRamp: Instead of a revenue-only kickoff event (or, as many companies call it, an RKO), we held an all-employee Company Kickoff (CKO). The goal? To get the entire organization engaged, aligned around this year’s priorities, and pumped to take our business to the next level.

So, how did it go? We had a blast and came away with a ton of learnings. Read on to see the top six highlights from our event, with pro tips on how enablement teams can tackle such a big and exciting event. 

Highlight #1: An inspiring theme 

Like any event, getting the theme right is critical to set the tone and energy for the overall experience. Our goals for our event this year were to inspire, educate, and celebrate, and we wanted the theme to reflect that. Through brainstorms with the executive leadership team, we landed on a fun theme that the whole company could tap into: Next Level, because that’s what we’re doing at WorkRamp this year, taking it to the next level! 

We were able to bring this concept to life by wrapping it around vintage, 8-bit video games, think Super Mario, Street Fighter, and Tetris. Check out some of the ways we brought this to life in the photos below. 

WorkRamp CKO

CKO SE Team

Pro Tip: People loved that we brought the theme to life through each touchpoint of the event, from swag to the presentations. Branding counts! Make sure you tie all the moving parts together through a strong theme to set the tone for your overall event. 

Swag CKO

Highlight #2: The leadership lineup

An SKO or CKO is when employees get to hear from executives about past performance across the organization and future company vision. It’s a time to celebrate all the accomplishments from the year before and motivate employees to gear up for the year ahead. 

We split up our executive presentations over the two days and kept the presentations to 45 minutes max. Led by our CEO, each executive leaned in heavily to our theme, Next Level, using graphics and language. Each executive gave us an overview of what they were excited about for the year ahead and covered other highlights to get everyone rallied around our goals. Our Marketing team surprised us with a virtual music video, we heard about some exciting achievements from our CRO, we had the opportunity to do an impressive roadmap review with our Product leaders, and we heard how we are going to kick butt overall this year from our co-founders.

Ultimately the presentations were fun and informative — added bonus, I can use all this content for my new hires to get them up to speed quickly on our goals for the fiscal year! 

Pro Tip: Don’t make sessions too long. Plan sessions for about 30 to 45 minutes with frequent 15-minute breaks. If you start seeing people’s eyes glaze over a bit, don’t be afraid to stop before the next session, have everyone stand up or stretch at their desks. 

Don’t forget to give about an hour for lunch and encourage people to get up and go for a walk or move. It helps people stay engaged, and will help avoid virtual-meeting fatigue. 

Highlight #3: Choose your own adventure with employee expertise 

As a company, we’re focused on developing our employees and giving people opportunities to help accelerate their careers. What better way to tap into employees’ talents than to give people the stage to present an area of expertise or passion in front of their peers? That’s exactly what we did! 

A few months before the event, we held an internal call for speakers. Employees would simply fill out a form with a topic they had in mind, and then someone from the Enablement team met with them to scope their idea and offer suggestions on how to best present the information and ideas around activities to make the training engaging. Then about a week before the event, we held dry runs with each presenter and offered any last-minute feedback. 

Each presenter had 25 minutes and based on the post-event survey results, everyone wanted more time in these sessions! Our topics ranged from ‘Selling with Empathy’ to ‘Mediation & Yoga for Stress Management’ to ‘ Salary Negotiation’.  

We were able to leverage our own WorkRamp Events feature to power this portion of the agenda and really reinforce the idea that learners could really “Choose their own learning adventure!” 

About three weeks before the event, we provided a course catalog for employees to review the available session and then opened up registration which was on a first-come, first-serve basis. Each session was capped at a certain number of attendees to encourage attendance to all sessions within that time frame. We ran 3 to 4 sessions per 25-minute time block, with two back-to-back. Two in the morning, two in the afternoon. Having learners register for their own sessions took the organizational load off of the Enablement team’s shoulders and empowered our employees to really be the masters of their own learning journey. Learn more about to use how the WorkRamp Events feature

Pro tip: In this situation, it’s Enablement’s job to help make sure the content being delivered is accurate and valuable and to help presenters feel confident in what and how they present their information. Set up workshops to review content with all speakers to make sure everyone is ready for prime time. We had a kickoff meeting with a member of our internal Instructional Design team to provide tips and tricks for how to hold engaging virtual meetings/trainings. As an added bonus, this is a great professional skill for your employees to gain! 

Highlight #4: Call in stellar guest speakers 

Guest speakers are a great way to both inspire and educate employees. At our CKO, we focused on bringing in motivating customers, thought-leaders, and experts on key topics. 

We hosted a panel with three of our customers for 45 minutes which was the highest-rated session of the entire event. The insights, excitement, and ideas our internal teams gained from that session are so incredibly impactful. 

Additionally, we had a volunteer group of internal employees present about DEI: what it is and how it can be impactful for companies like ours. Lastly, each day we had a keynote speaker offering their insights. The first session was from Jack Altman, CEO of Lattice, around what we can expect as a Series C company, and the second session was delivered by Alexis Ohanian on Inflection Points within business as well as your personal life. 

Alexis Ohanian

Pro tip: Guest speakers don’t have to be famous or expensive. People love hearing from customers, board members, partners, and other company friendlies. When it comes to guest speakers, it is most effective to partner with people that can tell great stories and educate your audience. 

Highlight #5: The energizers 

We all know that no CKO or SKO is complete without some good ‘ol fun and entertainment. At our recent CKO, we added a ton of “energizers” to help break up the day and give people, yes, energy! 

Here’s what our energizers looked like:

  • Virtual photo booth for fun pictures during the event
  • Cameos to get people pumped up from some fun and relevant celebrities
  • A virtual scavenger hunt to get people moving 
  • Music between sessions to keep the event moving with high-energy

WorkRamp photo booth

Pro tip: The photo booth was a great way to give people shareable content for social media. We encouraged everyone to include pets, kids, and family members in their pictures as well. With an added dash of fun virtual background and stickers, not only did employees get a fun takeaway to remember their experience, but this turned into a solid employer branding moment for us as well. 

Highlight #6: Recognition 

Perhaps the most rewarding part of any CKO event is getting to celebrate all the accomplishments across the team, and that was true for our CKO this year as well. 

Each Manager was given the opportunity to come up with meaningful awards for members of their teams. We set aside dedicated time within our agenda on the first day for each Manager to announce and explain the award and our Zoom chat window was lit UP with congratulations from their fellow colleagues. In a virtual environment, awards and recognition are incredibly important to make sure your employees feel valued and seen. 

WorkRamp Awards and Recognitions

Pro Tip: Instead of trophies or plaques, this year we sent fun, branded boxes with goodies to recognize employees. 10/10 recommend! 

The bottom line

Overall, the feedback we received was really phenomenal as far as satisfaction scores go. I’ve helped to plan several SKO events throughout my career and an 80 to 85 percent satisfaction score is what you aim for.  We received a 95 percent satisfaction rate which is truly spectacular! 

Regardless of online or in-person, the key is to make this time away from everyone’s everyday jobs worth it. And if you’re going to take them away from their day jobs, make sure management is bought into this time as well — meaning no emails or requests outside the event to distract them.

Leaders can really make a difference here and demonstrate the value. Make the content engaging and valuable and then listen and implement feedback for future events to continue to make them impactful for your audiences.

Ready to take your next CKO to the next level? Learn how WorkRamp’s All-in-One Learning Platform can help. Request a demo.

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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