President’s Club in paradise… or just an expensive bonding exercise no one asked for? 🏝️💸
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Every year, companies drop hundreds of thousands of dollars on President’s Club trips to places like Maui, Cabo, or some Caribbean resort with more drink tickets than strategy.
The intention?
Reward top performers
Build loyalty
Create “bonding moments”
The reality?
Most employees would rather have the cash
The same sales people win every year
And everyone else feels overlooked or resentful
Indeed.com recently bought out the entire Andaz Maui for their President’s Club — excursions, accommodations, the whole shebang. Impressive? Yes. Strategic? Maybe.
But it raises a bigger question: Is this even how today’s revenue orgs want to be recognized?
The Employee Eye Roll: “Thanks, But I’d Rather Have the Bonus”
Having been fortunate enough to be selected to go two President’s Clubs as a marketer, I was curious if people would rather have the cash or the trip?
I ran a quick poll on LinkedIn last week.
Overwhelmingly, 77% of people said they'd rather take the money instead of the trip.
No surprise.
In 2025, employees want flexibility, autonomy, and actual appreciation — not a forced vacation with Steve from Sales Ops and three days of small talk on a snorkel boat.
And let’s be honest: This isn’t a vacation. It’s just work with a different dress code and sunscreen.
Who Actually Drives Revenue?
Here’s where it really breaks down.
Most President’s Clubs still operate on an old-school model: reward the AEs who close deals. Period.
A modern President’s Club should reflect how value is actually created — cross-functionally, and modern GTM teams are cross-functional machines.
The CSM who saves a $300K renewal?
The lifecycle marketer whose nurture drove pipeline?
The RevOps leader who fixed the routing that unlocked speed-to-lead?
They all contributed to that number.
And yet, they’re not invited to the luau.
The Fix: Modernize the Model
Here’s how you fix the club without losing the spirit behind it:
Make it cross-functional
If your CRO is the only exec picking the winners, you’ve already failed. Let marketing, CX, and ops nominate their MVPs based on impact, not title.
Give them a choice
Trip or cash. I know this will be hard for some CEOs to hear but…Not everyone wants to drink with their boss on a beach. Let people opt into what actually motivates them.
Reward collaboration, not just quota
You want to build a high-performing revenue org? Recognize the teams who win together, not just the loudest voices in the room.
1. Sales + Revenue Roles
Yes, your quota-crushers should be there. That’s non-negotiable.
But include BDRs, not just AEs and AMs. Pipeline matters too.
2. Customer Success + Retention
Renewals and expansion are just as critical as net-new.
If someone saves a $500K churn risk? They belong on the beach.
3. Marketing, Ops, Product (maybe)
Did a lifecycle marketer crush a campaign that drove pipeline?
Did RevOps overhaul your GTM motion for scale?
Did Product launch something that unlocked new revenue?
If yes → reward them. If no → don’t.
4. Teamwork-Based Achievements
Introduce a team category — rewarding pods or squads that delivered exceptional cross-functional wins.
5. Let People Choose: Cash or Club
If you really want to modernize it? Give people the choice:
🏝️ Trip to Maui/Cabo/Caribbean island
💰 Equivalent after-tax bonus
Watch how much goodwill you earn from that one change.
So ask yourself:
Are you investing in true recognition… or just expensive peer pressure in paradise?
Let me know in the comments!
This is the free post for July. As a reminder, this newsletter is moving to monthly for free subscribes, and will continue weekly for paid subscribers. You can still save 40% on paid subscriptions through July 31, 2025. Thank you for reading!