December arrives and suddenly everyone remembers their clients exist. Gift baskets flood mailrooms. Holiday cards pile up on desks. Your thoughtful gesture becomes one of dozens competing for attention during the busiest gifting season of the year.

Then January hits, and the silence begins. Eleven months pass with no appreciation, no touchpoints, no reminders that you exist. By the time clients need your services again or have someone to refer, you’re a distant memory.

This is the problem with December-only gifting. In this guide, we’ll show you how to build a year-round strategy that keeps you top of mind every month, not just during the holidays.

The December Gifting Trap

Most professionals default to holiday gifting because it feels natural. There’s a built-in reason to reach out, and cultural expectations make gift-giving feel appropriate.

But this approach creates three significant problems:

You disappear for 11 months. A single December touchpoint cannot sustain a relationship. Clients forget you long before their next need arises or their friend asks for a recommendation.

You compete with everyone. During December, clients receive gifts from their accountant, their insurance agent, their banker, and a dozen other professionals. Your gift gets lost in the noise.

You seem obligated rather than genuine. Holiday gifts can feel like checkbox gestures. Clients know you’re sending them because it’s “the season,” not because you were thinking specifically about them.

The solution is spreading appreciation throughout the year when it’s unexpected, memorable, and uncontested.

The Foundation: Mapping Your Gifting Calendar

A year-round strategy starts with identifying the moments that matter.

Transaction-Based Touchpoints

These are tied to specific client milestones:

• Closing day or deal completion
• 30 to 90 days post-transaction (settling-in period)
• One-year anniversary
• Subsequent anniversaries (year two, three, five)

For real estate professionals, a home purchase anniversary is deeply meaningful. For financial advisors, the anniversary of signing an investment plan marks a relationship milestone. These dates create natural gifting opportunities unique to each client.

Calendar-Based Touchpoints

These apply broadly across your client base:

• Q1 (January to March): New year appreciation
• Q2 (April to June): Spring check-in
• Q3 (July to September): Mid-year touchpoint
• Q4 (October to November): Pre-holiday appreciation

Notice Q4 says October to November, not December. Gifting before the holiday rush ensures your gesture stands out rather than blends in.

Event-Based Touchpoints

These respond to specific occurrences:

• Referral received (immediate thank-you)
• Client birthday
• Business milestone or promotion
• Life events (new baby, retirement, etc.)

Combining all three touchpoint types creates a comprehensive calendar that keeps you present year-round.

Quarterly Gifting: A Simple Framework

If mapping individual client anniversaries feels overwhelming, start with a quarterly approach.

Q1: January to March

The post-holiday period is gifting dead zone. Almost no one sends appreciation in January or February, which means your gift stands out dramatically.

A Santoku Trimmer arriving in early February with a note saying “Wishing you a great year ahead” creates impact precisely because it’s unexpected. Clients remember the professional who appreciated them when no one else did.

This is also an excellent time for “just because” outreach to past clients you haven’t contacted recently.

Q2: April to June

Spring represents fresh starts. Clients are past tax season stress and open to positive touchpoints.

A custom cutting board or Entertaining Tool pairs well with warmer weather when people start hosting outdoor gatherings. For clients who grill, a 3-Piece Bamboo BBQ Set feels perfectly timed.

Q3: July to September

Summer is ideal for casual appreciation. Drinkware like 30oz Tumblers or Mini Vinnsulators fits the season perfectly. These items get used at barbecues, beach trips, and outdoor activities, creating repeated brand impressions during high-social months.

Q4: October to November

If you want to gift during the traditional appreciation season, do it early. A gift arriving in late October or early November beats the December rush and gets the attention it deserves.

Wine gift sets like a Bamboo Wine Box with Tools or Premium Kitchen Tools position well for upcoming holiday entertaining without competing against December’s gift avalanche.

Building Multi-Touch Campaigns

The most effective year-round strategies don’t rely on single gifts. They use multiple touchpoints that compound over time.

Research shows clients need several positive interactions before they think of you during referral conversations. One closing gift is nice but fades from memory. Three to five touches throughout the year keep you consistently present.

Example: 12-Month Client Journey

• Month 1 (Closing): Signature Series Wilmy Board with engraved closing date
• Month 3: Handwritten card checking in
• Month 6: Spatula Spreader with note about hoping they’re settled
• Month 9: Stemless Wine Tumbler as unexpected appreciation
• Month 12: Anniversary gift celebrating one year

This cadence maintains presence without overwhelming. Each touchpoint reinforces the relationship and keeps you top of mind.

Automating Your Year-Round Strategy

The biggest challenge with year-round gifting is execution. When you’re busy with active business, remembering anniversaries and quarterly touchpoints becomes impossible. Things slip through the cracks.

Automation solves this problem.

Automated Gift Campaigns let you set up multi-touch sequences that run automatically. You input client information once, and the system handles delivery at the intervals you specify.

Campaign tiers include:

• Tier 1: 3 Touches Over 1 Year at $113
• Tier 2: 4 Touches Over 1 Year at $169
• Tier 3: 5 Touches Over 1 Year at $246
• Tier 5: 6 Touches Over 18 Months at $393

These campaigns include handwritten cards, custom engraved gifts, and strategic timing designed to maximize relationship impact.

For event-based touchpoints like referral thank-yous, Drop Ship Gifts offer on-demand flexibility. When a referral comes in, you place a single order and the gift ships directly to your client within days.

Combining automated campaigns with drop ship flexibility creates a comprehensive year-round system that runs without constant attention.

Segmenting Your Client Base

Not every client needs the same level of attention. Segmenting helps you allocate resources appropriately.

Top Tier: High-value and active referral sources

These clients deserve the most comprehensive treatment. Consider Tier 5 or Tier 6 campaigns with multiple touches over 18 to 24 months.

Middle Tier: Standard clients with good potential

A Tier 2 or Tier 3 campaign with 4 to 5 touches over one year maintains presence without over-investing.

Foundation Tier: All past clients

At minimum, every past client should receive annual appreciation. Even a single yearly touchpoint keeps you on their radar.

This segmented approach ensures your best relationships get appropriate attention while still maintaining contact with your broader network.

Measuring What Works

Track which touchpoints generate the best responses. Note when clients mention gifts, when referrals come in, and which campaigns produce results.

Over time, you’ll identify patterns. Maybe Q1 gifts generate more responses because they’re unexpected. Maybe anniversary gifts produce more referrals because they hit during peak emotional moments. Use this data to refine your strategy.

Final Thoughts

December-only gifting leaves 11 months of opportunity on the table. A year-round strategy keeps you present, memorable, and top of mind when it matters most.

Start by mapping your gifting calendar across transaction milestones, quarterly touchpoints, and event-based moments. Use automation to ensure consistent execution. Segment your clients to allocate resources appropriately.

Stop disappearing after the holidays. Start building relationships that last all year.

Ready to create your year-round gifting strategy? Explore our programs or contact us to build a system that keeps you top of mind every month.