How Sidecar Health Transformed Their 300 Person Team Gathering Experience

When Sidecar Health CMO Kevin Knight needed to bring his 300-person team together, he faced the classic team travel paradox: these gatherings are absolutely essential, but the process of organizing them is painfully inefficient.

"The reality is that planning events is not a core strategic competency of the business, but it is a core strategic necessity of team building," Knight explains, hitting on the fundamental tension that companies of all sizes face.

For teams like Knight's at Sidecar Health, the traditional approach to planning gatherings creates a series of interconnected problems that drain time, money, and energy from the organization.

"The more time you have to spend on the logistics of planning the event itself, the less time you have to spend on the agenda and the details that matter most," Knight points out.

Let's be honest about what's really happening in most companies:

• Your options are severely limited. HR team (or whoever has been tasked with organizing) without specialized training default to checking just 2-3 hotels because nobody has time for more
• Your best people are doing the wrong work. Top talent gets pulled away from strategic priorities to handle basic travel logistics
• You're probably overpaying. Without proper RFP processes, competitive rates remain undiscovered
• The details that matter get missed. Room configurations, meeting spaces, and other critical elements fall through the cracks
• Last-minute bookings cost you extra. Slow approval chains mean higher rates and fewer options

For a company of Sidecar Health's size, these inefficiencies don't just waste time—they directly impact the bottom line across multiple team events every year.

‍

‍The Breakthrough Approach

Knight realized something fundamental: what if the solution wasn't hiring more people or accepting the inefficiency, but using technology to transform the entire process?

By partnering with Workgrounds, he could "achieve the results of gathering people in person without having to invest in building a team that is focused on events."

This insight allowed Sidecar Health to:

• Keep their team laser-focused on their actual business
• Deliver high-impact team gatherings that strengthen culture
• Dramatically reduce both the time and cost of planning
• Free HR from tasks that weren't driving strategic value

‍

How It Works: The Four-Step Process

Knight's playbook to get his team together followed a clear process that a team of any size can replicate. Here are the steps he took:

Step 1: Get Smarter About Team Locations

The first move is to leverage data you already have: where your people actually are. This seems simple, but it's something most companies completely miss.

"The number of times I have been to in-person events where it was super convenient for a few people, while the others have to trek across the country with a series of convoluted layovers, only to miss key parts of the gathering—that's terrible," reflected Knight. 

How Sidecar Health did it with Workgrounds:

• Quickly imported team location data
• Specified exactly what they needed the gathering to accomplish
• Let the platform identify truly optimal meeting spots based on actual travel time and convenience

"The ability to plug in the location of the attendees is completely game-changing," Knight emphasizes.

Step 2: Break Out of Venue Defaults

The traditional approach to venue selection is basically "where did we go last time?" or "where are our offices?" But this misses massive opportunities.

Knight discovered something counterintuitive: "Even though we have an office in LA, it is cheaper to mix it up and go someplace new and novel for an executive retreat rather than to go to the same old, same old. And everyone loves that."

What this unlocked for Sidecar Health:

• Fresh environments that sparked new thinking
• Cost savings by exploring less obvious locations
• Higher team engagement through novel experiences
• Stronger cultural connections outside the everyday office setting

Step 3: Let Hotels Compete (Without You in the Middle)

Here's where technology creates the most dramatic efficiency gains. Rather than manually reaching out to a handful of venues, the entire RFP process can be automated.

Knight was able to get valuable data that would have taken weeks in a matter of minutes:

• Instant RFPs to dozens of suitable venues
• Hotels actively competing to win Sidecar Health's business
• Zero back-and-forth emails or phone calls
• Comprehensive analysis of all costs, not just the headline room rate
• Standardized responses that made comparison actually possible

"If you can outsource the logistical details of travel and RFPs, contracts, and all that back-and-forth, you can spend that energy where it is much, much better spent," Knight explains.

Step 4: Design for Connection, Not Just Convenience

With the logistics handled, Knight could focus on what actually matters: creating an environment where meaningful work happens.

"Do you want to have a classroom style, or circular tables, or a U shape?" Knight considered. "If we're going to do working sessions, we either need a separate working space or the ability to have the room set up for that."

Sidecar Health's new focus included:

• Thoughtfully designed spaces that supported their specific objectives
• Activities engineered for meaningful team connection
• Environments that facilitated both structured and spontaneous interaction
• Details that reinforced their culture and values

‍

The Real-World Impact

For Sidecar Health, this approach didn't just feel better—it delivered measurable results:

Hours Back in Your Week: The planning process that used to consume Knight's team now happened largely in the background, giving everyone back time for their actual jobs.

Real Money Saved: Automated comparison shopping and earlier bookings meant Sidecar Health secured rates they never would have found manually. Knight could see the complete financial picture, including how flight costs balanced against hotel rates.

Gatherings That Actually Work: With the logistics handled, Knight could focus entirely on the experience: "With logistics tucked away, the people came into focus again: the experience we wanted them to have, and what we wanted them to come away from the event with."

No Need to Hire Event Staff: Sidecar Health delivered professional-quality gatherings without expanding headcount or diverting existing team members.

"By outsourcing this to Workgrounds, nobody had to take time away from their day job to plan an event," Knight explains.

‍

‍Five Principles You Can Apply Now

Knight's experience revealed five core principles that any organization can implement immediately:

1. Your team should focus on your business, not booking hotels. If event planning isn't your core competency, stop pretending it is.
   
   
2. Data beats gut feelings every time. Using geographic analysis of your team's locations will reveal optimal meeting spots you'd never have considered.
   
   
3. Automation isn't just faster—it gets better results. AI can analyze options and scenarios in ways that manual processes simply can't match.
   
   
4. The experience is what people remember. The venue, room setup, and overall environment directly impact whether your gathering achieves its objectives.
   
   
5. Flexibility creates better experiences. When you can easily adjust bookings on the fly, you can adapt to changing needs without the typical stress and cost.
   
   

By following these principles and implementing the approach that worked for Sidecar Health, your team can turn team gatherings from logistical nightmares into genuine strategic advantages—bringing people together efficiently while saving both time and money.

‍