How Sidecar Health Brought Their Sales & Marketing Team Together — Without Breaking A Sweat

Welcome reader,

I’m thrilled to share with you the first edition of The Gathering Ground—a newsletter that tackles the headaches we've all experienced when planning team gatherings. 

Each issue will share real stories from leaders who've cracked the code on efficient team travel while actually making these gatherings meaningful (not just expensive logistical nightmares).

But if you don’t want to continue getting this newsletter, you can simply unsubscribe at the bottom of this email. 

Let’s dive in!

Corralling teams with many people is a classic Goldilocks solution: there’s only one way that’s just right.

Today, Sidecar Health CMO Kevin Knight is going to tell you what he figured out.

No stealing time from the People team.

An easier way to dream of about faraway retreats.

“Check into” this issue of The Gathering Ground to hear from Kevin, learn what’s new on our platform, and get a little dose of industry updates.

Our Itinerary

🤖 Automation makes perfect
🦾 New Workgrounds Product Releases
🌎 Links heard ‘round the world
💭 Share your thoughts

AI: The Ultimate Travel Problem-Solver

Your team, whether it has 20 members or 100, needs to be on the same page.

That’s what in-person events are for.

But what else are in-person events? A pounding headache, and a logistics puzzle no one wants to deal with.

Kevin Knight (the Sidecar Health CMO) was tired of taking up People team/HR’s time with site research, flight research — research up to their eyeballs. The company cares about bringing staff together, but having a dedicated meeting planner on the team wasn’t in alignment with their business goals.

Enter automation.

Knight tapped Workgrounds’ platform to “achieve the results of gathering people in person without having to invest in building a team that is focused on events."

Next:

• He gathered up team location data (tech figures the best spot for everyone — actually, not with Google Maps or vibes)

• He let the hotels fight over him (automated RFPs took the work totally out of his hands, and got 50+ hotels involved at once) 

• He got options for setting up the perfect space (don’t worry about Socratic seminar-style setups when you get there)

And that left HR with lots of time to plan what really matters: team-bonding activities, group dinners, and fun little surprises.

With the very best flights and locations picked (we’re talking cost-effective, because everyone going to LA HQ isn’t necessarily as good as Denver), the company coffer had some more bucks to work with — whether they’re up-leveling the swag bags or keeping it close.

When you give tech the booking power, the travel is a breeze. 

Learn more about how he got out of the planning weeds — and saved money, too:
How Sidecar Health Transformed Their SKO team gathering experience

What's New on Workgrounds

We're always working behind the scenes to make planning your team events even easier—and this month we've rolled out several exciting updates:

1. See Your Savings at a Glance Ever wonder how much your group booking is saving you compared to standard retail rates? Now, proposals display the hotel's Best Available Rate (BAR) alongside your exclusive group rate. Instantly see and showcase your savings, making decisions simpler and impressing stakeholders easier.

👉 Discover how much your group saves vs. retail rates.

2. Flexible Proposal Exports Love spreadsheets? Us too. Now, export all hotel proposals directly into CSV format, making comparison and collaboration seamless.

👉 Learn more about proposal exporting

Got feedback or ideas for new features? We’d love to hear from you. Just reply to this email!

Points of Link-terest

A quick tour across the internet.

• PhocusWire says AI is slashing corporate travel costs—if you can handle the learning curve.

• Dropbox shares how onsites, offsites, and team retreats drive real business results—even for "virtual-first" teams.

• This Reddit thread about company events is brutally honest — and maybe you should take notes.

• Skift predicts your 2025 hotel stay will be smarter, smoother, and powered by AI.

Tell Us How You Really Feel

“The most team trips I’ve simultaneously planned at once: ______” 

Reply to this email with your response. We’ll share our favorites in the next newsletter!

Onward!

Well, we’re taking off.

Keep your seatbelts buckled, and we’ll see you soon. 

To see Workgrounds’ platform in action, book time with our founder.