Sales & Incentives
The reward only works if it feels earned. Here's how to design an incentive trip your best reps chase all year — without defaulting to another resort ballroom.
Presidents Club is one of the few line items in a sales budget that pays for itself twice — once when the winners feel genuinely recognized, and again the following year when the rest of the team works harder to qualify. But most incentive trips underperform for the same reason: they're booked like a conference, not designed like a reward. A block of hotel rooms, a banquet room, a branded step-and-repeat, and a "free afternoon." Nobody chases that.
The trips people talk about for years share a few traits. Here's what to build around.
Top performers can book a nice hotel themselves. What they can't buy is exclusivity — a place their company took over entirely, where every person they see for three days is someone they earned their way in beside. A private estate or buyout property beats a five-star resort at the same price point precisely because there's no other group in the lobby diluting the moment. If your winners can tell the difference between your incentive trip and a sales conference, you've already lost the magic.
Twelve to twenty-five people is the sweet spot. At that size, the CRO can have a real conversation with every winner, spouses get folded into the group instead of orbiting it, and dinner happens at one table instead of eight. Once you cross fifty, you need a ballroom, a stage, and an AV crew — and the whole thing starts to feel like a mandatory event again.
One evening. One hour. Named awards, specific stories about how each person won, and the CEO or founder in the room saying it out loud. That's the entire "business" content of the trip. Resist the temptation to bolt on a product roadmap session or a "quick" pipeline review — the second your winners feel like they're working, the reward converts into an obligation and the ROI evaporates.
Planning a working offsite instead? Grab our ready-to-use, hour-by-hour agenda template and customize it for your team.
Get the Free TemplateThe most memorable incentive trips trade poolside downtime for something with a story attached: a guided wildlife morning in Yellowstone's Lamar Valley, fly fishing the Henry's Fork, snowmobiling groomed trails through the Island Park caldera, or horseback riding into open country. Adventure doesn't mean strenuous — it means the photo they send their family looks nothing like a hotel. Always offer a lower-intensity parallel option so nobody feels sidelined.
Bringing spouses and partners is what turns a trip into a genuine reward, because it recognizes the household that absorbed the late nights and travel. And nothing undermines that faster than logistics friction. Private chef instead of restaurant reservations, transportation arranged, no one reaching for a wallet all week. When there's nothing to coordinate, people relax — and relaxed people bond.
The moments winners describe afterward are almost never on the agenda: the hot tub conversation, the late round in the game room, the hour by the firepit where a rep and the VP of Sales finally talked candidly. Build in the anchors — one adventure, one great dinner, one awards moment — and leave the rest genuinely open.
Most teams run Presidents Club four to ten weeks after the fiscal year closes, once numbers are certified but before the new year's pressure fully sets in. In Yellowstone country, that lands in a beautiful window: February and March deliver deep snow and world-class snowmobiling, while April and May bring shoulder-season quiet and emerging wildlife. Both avoid peak summer park crowds — and peak summer pricing.
Somewhere like Iron Slide Lodge — an 8,000 sq ft private estate 30 minutes from Yellowstone, taken over entirely by your group — gives an incentive trip the one thing a resort can't: the feeling that this place was reserved for them, because it was.
← Back to ResourcesExclusive use of the entire estate, private chef, adventure, and evenings by the fire — all on one invoice.