How to Build a Company Offsite with Points: A Step-by-Step Guide for Small & Medium-Size Businesses
Spending $30K+ per month on business cards? You could be sending your team on an unforgettable offsite—in business class. Learn how SMBs are turning everyday expenses into all-expenses-paid trips using points, not P&L. Step-by-step breakdown. Big ROI. No fluff.
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Company offsites are more than just a perk — they’re a high-leverage investment in culture, retention, and alignment, especially for small and mid-sized businesses. The biggest blocker? Cost. But if your company is spending $30K or more per month on corporate cards, you may already have the budget — in points.
Instead of cash, smart SMBs are using credit card rewards to fund premium offsites. Flights and hotels are where points deliver the most value, often covering 60–80% of total expenses. A trip that might cost $30K+ in cash could be executed for under $10K out-of-pocket with the right setup.
The key isn’t opening new cards — it’s optimizing your current spend:
- Centralize major expenses like ad spend and software onto high-reward cards (e.g., Amex Business Gold, Chase Ink Preferred).
- Maximize category multipliers to earn 3x–5x points on your largest budget items.
- Use employee cards that roll into a single rewards pool for centralized redemptions.
- Prioritize transferable rewards programs like Amex Membership Rewards and Chase Ultimate Rewards.
Planning travel for 10+ people is complex. You’ll need to book flights early (up to - but not always - 355 days out), split redemptions across airlines if needed, and negotiate hotel blocks using a mix of points and cash.
One agency we worked with cut their offsite cost from $38K to $7K by shifting spend strategy and using 1.4M points.
If you’re not optimizing your card spend, you’re leaking value every month. A well-planned offsite can drive loyalty, unlock motivation, and make your culture tangible — all without straining your P&L.
Start with a points audit, and turn your existing spend into your team’s most memorable week of the year.
Everything else you need to know is just below 👇🏻
Company offsites are no longer just a “nice-to-have.” For small and mid-sized businesses, they’re a mission-critical opportunity to build culture, improve retention, and align high-performing teams. But here’s the secret: they don’t have to destroy your budget.
If your company is spending $30K or more per month on corporate cards, you could already have the budget — in points. This guide shows you how to turn everyday business expenses into a fully-funded offsite that drives ROI far beyond its cost.
Why Company Offsites Are Strategic — Not Just Perks
It’s tempting to think of offsites as glorified team vacations, but that’s a narrow lens. Done right, a company offsite can drive deeper alignment, renew momentum, and help retain top performers in ways Slack and Zoom never could.
Connection in a Distributed World
As remote and hybrid work becomes the norm, in-person time becomes more valuable. A quarterly or annual offsite becomes the place where teams finally meet face-to-face, tackle strategic challenges, and renew trust.
Culture Signal to Your Team
Hosting a well-planned offsite sends a clear message: we invest in our people. That’s powerful for team morale — and even more powerful for retention. Especially if you're a growing company asking a lot from a small team.
A Recruiting Differentiator
If you're competing for talent against larger brands, the promise of a company-paid offsite at a resort in Costa Rica or a villa in Portugal makes you instantly more attractive. These trips give your culture narrative an edge.
Budgeting: Cash vs. Points (and How to Blend Them)
Let's get real: offsites can be expensive. But when you use points smartly, you dramatically reduce out-of-pocket costs — without sacrificing quality.
A Sample Cash Budget for 10 People
| Category | Cost |
|---|---|
| Flights (roundtrip, international) | $10,000–$12,000 |
| Hotels (5 rooms, 4 nights) | $12,000–$18,000 |
| Food, transport, excursions | $5,000–$10,000 |
That adds up to $27,000 to $40,000, which for many SMBs, feels like a luxury you can’t afford.
A Smart Blended Budget
Here’s how that same trip might look with a points-first strategy:
| Category | Cash | Points |
|---|---|---|
| Flights | $500 (taxes/fees) | 900,000 Amex/Chase points |
| Hotels | $1,000 (incidentals) | 600,000 Hyatt or Marriott points |
| Dining + Activities | $6,000 | Paid with saved cash or cashback cards |
With smart planning, you can slash your hard costs to under $10,000, while still delivering a high-end international experience.
The Right Card Strategies: How to Earn Fast for Group Redemptions
You don’t need to open 10 new credit cards. The fastest way to earn points for an offsite is by structuring your existing business spend.
1. Centralize Expenses
Many SMBs let departments or individuals pay vendors on a mix of personal cards, low-earning corporate cards, or bank debit. Instead, consolidate major recurring expenses — like advertising, software, and vendors — onto high-earning rewards cards.
- Ad spend should go on cards that offer 4x–5x in that category.
- Software, shipping, and travel have their own card optimizations.
ProTip: Centralizing spend doesn’t just simplify your books — it multiplies your point-earning potential.
2. Maximize Category Multipliers
Choose cards with bonus earning categories that match your OpEx. For example:
- Amex Business Gold earns 4x on top two categories (like online ads or software).
- Chase Ink Preferred earns 3x on shipping, travel, ads, and digital services.
A business spending $50K/month can easily earn 1.5M+ points per year just by optimizing category matches.
3. Control Employee Cards and Pool Points
Instead of letting every team lead rack up points in separate silos, assign employee cards that link back to a master account. You keep control of the rewards — and make offsite planning a whole lot easier.
4. Use Transferable Points Programs
Stick to flexible currencies like Amex Membership Rewards, Chase Ultimate Rewards, and Capital One Miles. These allow you to transfer points to airlines and hotels — often at 1:1 value — instead of being locked into one provider.
Hotel + Flight Redemptions for Groups: Tips and Pitfalls
Booking a personal vacation with points is easy. Planning a 10-person international offsite with them? Not so much.
Here’s how to navigate the tricky stuff.
Flight Booking Strategy
Group award space — especially in business class — is limited. Many airlines release availability 330 to 355 days in advance, and that’s when you want to strike.
Prioritize programs with solid transfer partners and availability, such as:
- United MileagePlus
- Air Canada Aeroplan
- Avianca LifeMiles
- British Airways Avios
Don’t expect to find 10 award seats on a single flight last-minute. Flexibility is key.
Hotel Planning for Teams
Getting five or more rooms at a hotel using points requires forethought. Award space can be limited, and blackout dates are common during peak seasons.
Your best bets:
- Hyatt: Excellent redemption value, especially at luxury properties
- Marriott: Large global footprint and more room availability
- Hilton: Flexible policies and good for mixing cash + points
Negotiate directly for room blocks — even if some are points, and others are paid.
Real Client Example: A Marketing Team Offsite in Costa Rica
A 17-person marketing agency based in Texas wanted to reward their top team leads and align on Q3 strategy. They were already spending $60K/month on ad platforms, contractors, and software but had no centralized credit card strategy.
What We Found:
- They had over 1.2 million Amex points spread across three accounts.
- Most spending was going on 1x cards — missing huge multiplier potential.
- Their previous offsite had cost $28K, all out of pocket.
What We Did:
- Shifted ad and software spend to Amex Business Gold and Chase Ink Preferred.
- Centralized all points into a single redemption account.
- Booked 10 business class flights to Costa Rica using 900,000 points.
- Reserved 5 ocean-view rooms at the Andaz Papagayo using 500,000 Hyatt points.
- Covered team dinners, excursions, and local transport with a $6,500 cash budget.
Trip value: ~$38,000
Out-of-pocket spend: ~$7,000
Internal feedback: “Best week we’ve had as a team — ever.”
Common Pitfalls and How to Avoid Them
Planning a points-funded offsite is high-reward, but not without risk. Here are the traps we help SMBs avoid:
- Waiting too long to book flights: Award seats are limited. 10+ seats? Even more so.
- Assuming points transfer instantly: Some hotel and airline programs take days to process transfers.
- Ignoring blackout calendars: Planning around holidays or conference seasons can kill availability.
- Relying on one program: If you’re all-in on just Amex or just Marriott, your options are limited.
Ready to Build Your Offsite?
If you’re putting $30K–$100K/month through corporate cards and haven’t planned an offsite with points, you’re leaving real value on the table.
This isn’t about chasing “free travel.” It’s about making a strategic investment in team cohesion, culture, and retention — while leveraging what you’re already spending.
Here’s what to do next:
- Get a points audit: Know how many points you have, where they are, and how they’re earning.
- Set a 12-month goal: Plan your offsite timeline, team count, and destination early.
- Structure your spend: Align card strategy to your business model so every dollar gets you closer to your trip.
Or better yet — let us at UpNonStop handle it.
Final Thoughts
Company offsites don’t have to be a line item you dread. When funded with points, they become a smart, scalable way to deepen alignment, show appreciation, and unlock retention — all without crushing your bottom line.
You already have the spend. You’re already earning the points. Now it’s time to use them.
Start with a free points audit — and turn your next offsite into your team’s favorite week of the year.
