If you're running or supporting an enterprise sales team, you already know the deal: relationships matter, and sometimes a well-timed gift can open doors. But picking B2B gifting software is a minefield of bold claims, buzzwords, and platforms that look good in demos but flop in real life. This guide is for sales leaders, ops folks, and anyone stuck with the “find us a gifting platform” job. We’ll skip the nonsense and get straight to what actually works—and what to ignore.
Step 1: Get Clear on Why You’re Sending Gifts
Before you even start Googling, nail down your real goals. If you just want to send branded mugs, you don’t need fancy software. But if you want to:
- Warm up cold prospects
- Nudge deals stuck in your pipeline
- Thank top clients or partners
- Automate or track ROI
…then you’ll need more than a bulk order of tchotchkes.
Pro Tip: Don’t let “everyone else is doing it” be your reason. Gifts that look forced or generic can backfire. Make sure your team actually wants to use this tool, or it’ll gather dust.
Step 2: Make a Shortlist of Must-Have Features
Don’t get distracted by flashy features you’ll never use. Focus on what’ll actually help sales folks close deals or save time. Here’s what to look for:
- CRM Integration: If it doesn’t plug into Salesforce, HubSpot, or whatever you use, move on. Manual data entry is a killer.
- Gift Options: Can you send more than just cookies and coffee mugs? Look for variety—digital gifts, charity donations, experience vouchers, etc.
- Recipient Choice: Can recipients pick what they want? Forced swag often ends up in the trash.
- Global Reach: Can you send gifts internationally without headaches? Customs, shipping costs, and local options matter.
- Tracking & Reporting: You’ll need to prove ROI, even if it’s just to yourself. Can you see who accepted a gift, when, and whether it moved the needle?
- Automation & Campaigns: Can you trigger gifts based on pipeline stage, customer anniversaries, or events?
- Compliance: Is there control over gift limits, recipient eligibility, or company policy? This matters in regulated industries.
Nice-to-Haves (But Not Dealbreakers): - White labeling (put your logo on gift emails) - Budget controls for teams - API access, if you’re advanced
What to Ignore: - Gimmicky “AI-powered” gifting suggestions (they’re usually just filters) - Social feed features (“see who else sent a mug!”) - Over-designed dashboards you’ll never use
Step 3: Test the User Experience (for Both Sides)
Lots of gifting platforms look slick in sales pitches but are a pain for real users. Insist on a trial or at least a test drive. Test these things:
- Sender Experience: Is sending a gift fast, or does it take 10 clicks? Can you do it from within your CRM?
- Recipient Experience: Does the recipient get a clunky email that looks like spam, or a personal note? Try sending one to yourself.
- Redemption: How easy is it for the recipient to claim, swap, or decline the gift? If someone has to create an account, that’s a red flag.
Pro Tip: Ask about failed deliveries, expired gift links, and what happens if a recipient ignores the gift. You’ll learn more from how they handle problems than from their pitch deck.
Step 4: Vet the Vendor’s Gifting Catalog
Some vendors brag about “thousands of gift options,” but half of them are cheap swag or unappealing. Look for:
- Quality over quantity: Are the gifts things you would actually send—or want to receive? Check brands, price points, and variety.
- Digital options: Physical gifts can be a hassle (shipping, customs, delays). Digital cards, experiences, and donations are instant and often more relevant.
- Global coverage: If your prospects or clients are worldwide, make sure the catalog isn’t just US-centric.
Don’t just take their word for it—ask for a live catalog demo or sample list.
Step 5: Understand Pricing (and Watch for Gotchas)
Gifting software pricing is all over the map. Here’s what to watch for:
- Subscription vs. Pay-As-You-Go: Some charge a platform fee, others a per-gift fee, and some both.
- Markups: Are the gifts sold at retail price, or is there a hidden markup? Some vendors quietly inflate prices.
- Unused credits: What happens to leftover gift credits at the end of your contract?
- Implementation fees: Are there setup costs? Training fees?
- Minimums: Some vendors require a minimum annual spend.
Pro Tip: If a vendor pressures you to sign a long-term contract before a trial or pilot, be wary. You don’t want to get locked in with a dud.
Step 6: Check Security, Compliance, and Support
Enterprise teams can’t afford slip-ups with data or compliance. Ask:
- Data security: Is the platform SOC 2 compliant? How do they handle recipient data?
- Gift policy controls: Can you set limits by recipient, team, or deal size?
- Support: Is there real, responsive support, or just a ticket system that disappears into a void?
If you’re in a regulated industry (finance, healthcare), make sure the vendor knows the rules. Some gifting platforms have compliance modules—ask to see them in action.
Step 7: Run a Pilot Before Rolling Out Company-Wide
No matter how good the demo looks, you won’t know if a gifting platform fits your workflow until you try it. Run a small pilot with a handful of reps and real prospects. Measure:
- Adoption: Do reps actually use it?
- Response rates: Are recipients engaging?
- Impact: Did it help move deals forward?
Gather honest feedback and be ready to bail if the platform doesn’t deliver. Don’t let sunk costs or vendor pressure sway you.
Step 8: Ask for Real References (and Not Just the Happy Customers)
Every vendor has a highlight reel of happy customers. Ask to speak with users who’ve had issues, switched away, or had low usage. You’ll get a more honest picture.
Also check independent review sites (like G2 or TrustRadius) for recurring complaints—especially about customer support, billing, or catalog quality.
Step 9: Don’t Ignore the Boring but Important Stuff
- Legal/Procurement: Can your legal and procurement teams sign off quickly, or are there red flags?
- Implementation timeline: Will it take weeks to set up, or can you be live in days?
- Scalability: If you double your team or use cases, can the platform keep up?
Step 10: Review Top Contenders (But Don’t Get Stuck in Analysis Paralysis)
There are a bunch of options out there—Alyce, Sendoso, Reachdesk, and Corporategift are the names you’ll keep seeing. Each has strengths and quirks. Don’t waste weeks overanalyzing. Pick two or three, run a pilot, and see which one fits your real-world needs (not just your wishlist).
Pro Tip: The “best” gifting software is the one your team actually uses, not the one with the most features.
Gifting software shouldn’t be complicated. Get clear on your goals, focus on must-have features, and demand a real-world trial. Keep it simple, don’t fall for hype, and remember: it’s about building genuine connections, not just sending stuff. Start small, learn fast, and tweak as you go.