July 28, 2025

From Seasonal to Strategic: The Complete Corporate Gifting Playbook

Danielle Falzone
By 
Danielle Falzone

Senior Manager, Demand Generation
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You open your front door, and there is a package with your name on it. It's not your birthday. It's not a holiday. It's not an [insert special occasion] Day gift.

It's not from Amazon or Chewy or Wayfair.

You check with your partner, and they didn't order it. Your kids? Nope.

You open the package, and a wave of positive emotions overtakes you. The feelings are real, visceral — and supported by psychology.

Jessica Andrews-Hanna, an associate professor in the Department of Psychology in the College of Science at the University of Arizona, said, "Evidence from brain imaging ... suggests that ...... receiving gifts activate core areas of our brain associated with reward and pleasure. These brain regions also stimulate the neurotransmitter dopamine" (source).

Receiving gifts is like doing drugs.

Okay. Perhaps not exactly, but this demonstrates the power — and the positive brain activity — caused by gifting.

Note: There is also extensive research showing the positive emotional impact on the gift giver, but that's for another article.

A business can also create this emotional impact by sending a gift to an individual (buyer or prospect). The opportunity to build relationships is real.

Bonus: Personalized gifting can increase deal close rates by 22%.

However, not all corporate gifting is created equal. There is a significant difference between traditional and strategic corporate gifting. And you don't have to reserve gift-giving for special occasions — you can make a case for implementing a year-round approach (with measurable ROI).

If done correctly, strategic gifting is a relationship investment.

This article will help you harness this gift-induced dopamine response to transform gifting from a seasonal afterthought into a powerful, year-round relationship-building engine that drives measurable pipeline growth. 

But first, why do most companies get this wrong?

Why most gifting strategies fall short

Besides Sendoso, there are a handful of other companies that offer a gifting and direct mail platform. 

When used properly, they can be every effective. However, revenue teams implementing these systems often bump into three key issues.

  1. They have a seasonal/one-off mentality ... that limits pipeline impact
  2. They have not figured out how to scale the personalization ... without burning out teams
  3. They are suffering from "generic outreach fatigue" ... which is drowning out meaningful connections

Traditional gifting does not work.

So, how do we overcome these three problems? How do we ensure our gifting program stands out in the crowded marketplace?

First, we draw on social and behavioral sciences.

The psychology of standing out in a crowded marketplace

Psychology is the scientific study of mind and behavior, focusing on understanding how people think, feel, and act.

Gifting is all about how people "think, feel, and act."

You see where we are going, right? Without getting too science-y, let's break it down.

Physical experiences typically command full attention and complete focus. They activate multiple senses at once to create a richer memory. This full attention and multi-sensory experience is challenging to replicate using digital-only methods.

Physical objects (think: gifts) have distinct features — textures, weights, temperatures, and imperfections — all of which create unique "memory markers." 

They don't compete with digital distractions, such as notifications, pop-ups, or multitasking demands. They just ... are.

TL;DR: Tangible experiences beat digital ones in creating lasting and memorable experiences.

However, there's another psychological principle at work that makes strategic gifting particularly powerful in B2B relationships: reciprocity — one of the most powerful psychological principles in human behavior.

When someone does something nice for us, we feel psychologically compelled to return the favor, not just because we want to be nice or seem polite. This feeling is deeply ingrained (hardwired!) in how we maintain social relationships and build trust.

In a year-round gifting program, the reciprocity principle is even more important. 

When you only give gifts during the "traditional" seasons, you create a "reciprocity moment,” one that fades quickly. Year-round strategic gifting creates multiple reciprocity touchpoints throughout the relationship, building what psychologists call "reciprocity debt." You know, that feeling of obligation and goodwill toward a person, company, or brand.

Next, we recognize that strategic gifting has a positive impact on your organization.

The business impact of strategic gifting

Strategic gifting yields real ROI.

➡️Increased pipeline growth

➡️Higher engagement rates

➡️Faster deal velocity

Strategic gifting generates measurable outcomes.

➡️Higher conversion rates

➡️Improved brand recall

➡️Increased customer loyalty

Why? Direct mail is easier to understand as it requires 21% less cognitive effort to process and generates much higher brand recall (Source: Sendoso). Strategic gifting taps into this same principle through tangible, memorable experiences.

One example: Business planning software company, Anaplan generated $65M in pipeline and $30M in recognized revenue from a single Sendoso holiday campaign.

When done correctly, strategic gifting means your prospects are engaged throughout the year, not just during special occasions and specific seasons.

The "always-on" gifting strategy

A year-round gifting program helps to break through the dreaded digital fatigue and replace it with strategic timing, especially if you are competing with a "digital-only" world.

These tangible touchpoints will cut through notification overload and introduce a "surprise factor" — one that sits outside traditional gifting seasons.

It's time to rethink the gifting calendar, to move from reactive to proactive gifting strategies.

A few examples of how:

  • Create quarterly touchpoint opportunities that competitors miss
  • Build in lesser-known holidays* and seasonal moments for differentiation
  • Focus on a consistent brand presence throughout the buyer journey

*Did you know? National Ice Cream 🍦Day was on Sunday, July 20, 2025.

The key is moving beyond calendar-driven gifting to milestone-based opportunities. Instead of waiting for holidays, successful companies trigger gifts around customer lifecycle moments (think: onboarding successes, contract anniversaries, and account expansions). They celebrate project-based achievements such as launches, completions, and significant milestones that matter to prospects.

And don't forget to celebrate special employee events, such as promotions, work anniversaries, or industry recognition. These are more opportunities to create authentic, relationship-building moments that feel genuine rather than transactional.


If possible, automate these lifecycle and achievement-based triggers so that teams can consistently show up for the moments that matter most to prospects — turning relationship building from a manual task into a strategic advantage.

Sounds great, but what about burnout?

Personalizing at scale without burning out the team

Most teams fail because they focus more on growing contact lists and less on creating meaningful individual experiences.

Many teams are "resource-constrained," simply not having the capacity to scale and sustain these year-round programs.

Even worse, the "personalization trap" can lead to generic campaigns. Trying to personalize every single gift or touchpoint individually often leads to worse outcomes than a well-designed systematic approach.

The trap starts with good intentions: "Every gift must be completely unique and personally researched," which creates a resource drain (and keeps sellers from selling). Over time, the personalization feels forced, leading to obvious, shallow gestures (think: company-branded mugs, generic gift cards) that backfire into the not-personal-at-all world.

Examples of trap gifts include sending:

  • Golf accessories to anyone who mentions golf once on LinkedIn
  • Company-branded items that feel like promotional swag
  • Generic "congratulations" gifts for any company announcement
  • Gift cards with no context or connection to the relationship

Here's how to do it right, at scale.

Create template frameworks that feel custom

The secret isn't always "do more research." This is where technology — smart tech — comes into play.

Smarter systems use template frameworks that feel personal while remaining systematically manageable.

Develop messaging templates that can be customized with simple variables — company name, recent achievement, or industry challenge — while maintaining an authentic, personal tone. The key is creating templates that sound like they were written specifically for that recipient, not fill-in-the-blank form letters.

Here are 20+ email templates to use in your next gifting campaign.

Consider tiered gifting

Implement tiered gifting strategies that allocate resources based on the value of the relationship and the potential deal size/value. Your highest-value prospects receive premium, more personalized experiences, while earlier-stage contacts get thoughtful but streamlined touches.

Maximize impact.

Manage costs.

Ensure the team does not burn out.

Learn how Cradlepoint grew its contact list and developed a tailored approach to tiered gifting, resulting in one direct mail campaign that generated $2.36M in opportunities and led to 50 demo meetings.

However, to really take your program to the next level while also ensuring its sustainability year-round and into the future, you must prove its value.

Show me the money (metrics): A mini-case study of success

A year-round corporate gifting strategy has to start with small wins. If you can prove the value in a single campaign, the budget will be there for multiple programs. Soon, multiple programs will turn into an always-on, year-round strategy.

You have to start somewhere. And that somewhere for PatientPop, a healthcare marketing and practice growth platform, was to believe in the power of direct mail.

PatientPop's Marketing Programs Director, Brian Clevesy, transformed the company's struggling direct mail program by switching to Sendoso's corporate gifting platform. Initially skeptical of direct mail, Clevesy utilized targeted cookie* deliveries to medical offices, turning treats into effective door-openers for sales demos.

Within six months, PatientPop broke company records, generating seven-figure pipeline results and increasing booked demos by 19%. The strategy involved making direct mail exclusive to top-performing sales reps and focusing on shareable treats that delight entire medical offices.

This approach not only revitalized PatientPop's B2B marketing but also earned Clevesy a promotion to Marketing Programs Director.

*yes, real cookies 🍪

Data. Metrics. ROI.

Newly promoted Clevesy now has a strong case to be made for requesting a larger budget, which could eventually lead to a year-round gifting program.

It's time to get started

It's time to stop treating corporate gifting as a December expense and build it into a year-round relationship engine.

✅PatientPop's transformation from skeptical direct mail user to seven-figure pipeline generator over a short 6-month period proves what happens when you apply strategic thinking to corporate gifting.

✅Cradlepoint's $2.36M in opportunities from a single tiered campaign demonstrates the power of systematic personalization.

✅Anaplan's $65M pipeline, thanks to strategic timing, shows what's possible when you move beyond seasonal thinking.

The opportunity is clear and there for the taking. Instead of sending generic one-off holiday gifts to customers and prospects (what your competitors are doing), consider building relationships, creating reciprocity debt, and driving pipeline growth. Every. Single. Quarter.

As mentioned, science supports gifting. Remember what Jessica Andrews-Hanna, Psychology professor at the University of Arizona, said about dopamine? " ... receiving gifts activate[s] core areas of our brain associated with reward and pleasure. These brain regions also stimulate the neurotransmitter dopamine."

Digital outreach cannot replicate the “dopamine effect.”

Fortunately, the technology to execute a year-round corporate gifting program at scale exists.

Note: This tech also helps revenue teams double win rates, 6x second call rates, and close deals 29% faster.

Strategic gifting works. Data and science support it. It's time to start treating relationship building as a year-round program ... not a one-off campaign.

Download the Go-To Guide For Corporate Gifting eBook to learn more.

Frequently Asked Questions

1. What is the psychological impact of receiving gifts, and how does it apply to business?

According to Jessica Andrews-Hanna, an associate professor at the University of Arizona, "Evidence from brain imaging suggests that both giving gifts and receiving gifts activate core areas of our brain associated with reward and pleasure. These brain regions also stimulate the neurotransmitter dopamine." This creates real, visceral positive emotions that businesses can harness to build relationships with buyers and prospects. The psychological impact is so powerful that personalized gifting can increase deal close rates by 22%, making it a strategic relationship investment rather than just a nice gesture.

2. What are the three main problems with traditional corporate gifting strategies?

Most gifting strategies fail due to three key issues: (1) A seasonal/one-off mentality that limits pipeline impact by restricting gifts to holidays and special occasions; (2) Inability to scale personalization without burning out teams, leading to either generic gifts or unsustainable manual processes; (3) "Generic outreach fatigue" where meaningless corporate gifts get lost in the noise and fail to create genuine connections. These problems prevent gifting from becoming the strategic relationship-building tool it could be.

3. Why do physical gifts create a more lasting impact than digital experiences?

Physical experiences command full attention and complete focus, activating multiple senses simultaneously to create richer memories. Physical objects have distinct features, such as textures, weights, temperatures, and imperfections, that create unique "memory markers." Unlike digital experiences, they don't compete with notifications, pop-ups, or multitasking demands. Direct mail requires 21% less cognitive effort to process and generates much higher brand recall than digital alternatives, making physical gifts more memorable and impactful for relationship building.

4. How does the psychological principle of reciprocity work in strategic gifting?

Reciprocity is one of the most powerful psychological principles in human behavior - when someone does something nice for us, we feel psychologically compelled to return the favor. This feeling is hardwired into how we maintain social relationships and build trust. Year-round strategic gifting creates multiple reciprocity touchpoints throughout relationships, building what psychologists call "reciprocity debt" - that feeling of obligation and goodwill toward a person, company, or brand. This is more powerful than seasonal gifting, which creates only momentary reciprocity that fades quickly.

5. What does an "always-on" gifting strategy look like?

An always-on gifting strategy moves beyond calendar-driven seasonal gifting to milestone-based opportunities. Instead of waiting for holidays, successful companies trigger gifts around customer lifecycle moments (onboarding successes, contract anniversaries, account expansions), project-based achievements (launches, completions, milestones), and employee events (promotions, work anniversaries, industry recognition). This approach creates quarterly touchpoint opportunities that competitors miss, utilizes lesser-known holidays for differentiation, and maintains consistent brand presence throughout the buyer journey.

6. How can teams personalize gifting at scale without burning out?

The key is avoiding the "personalization trap" where teams try to make every gift completely unique. Instead, successful teams create template frameworks that feel custom using smart technology. This includes developing messaging templates with simple variables (company name, recent achievement, industry challenge) while maintaining an authentic tone, and implementing tiered gifting strategies that allocate resources based on relationship value and deal size. High-value prospects receive premium experiences while earlier-stage contacts get thoughtful but streamlined touches, maximizing impact while managing costs and preventing burnout.

7. What are examples of ineffective "trap gifts" that should be avoided?

Trap gifts include sending golf accessories to anyone who mentions golf once on LinkedIn, company-branded items that feel like promotional swag, generic "congratulations" gifts for any company announcement, and gift cards with no context or connection to the relationship. These gifts often feel forced and obvious, rather than thoughtful, and can backfire into the "not-personal-at-all" category. They result from trying to personalize everything individually rather than using a well-designed systematic approach.

8. Can you provide real examples of successful strategic gifting campaigns?

Several companies demonstrate strategic gifting success: PatientPop's Marketing Programs Director Brian Clevesy used targeted cookie deliveries to medical offices, generating seven-figure pipeline results and increasing booked demos by 19% within six months. Cradlepoint's tiered gifting approach generated $2.36M in opportunities and led to 50 demo meetings from a single campaign. Anaplan generated $65M in pipeline and $30M in recognized revenue from a single Sendoso holiday campaign, demonstrating the power of strategic timing and execution.

9. How should teams measure ROI and prove the value of year-round gifting programs?

Teams should start with small wins to prove value before expanding to year-round programs. Key metrics include pipeline generated, opportunities created, demo bookings, deal velocity, and conversion rates. PatientPop's success story demonstrates how proving value in a single campaign (seven-figure pipeline results) can lead to budget approval for expanded programs. The approach involves making data-driven cases with concrete metrics like influenced pipeline, meeting bookings, and revenue attribution to justify continued investment in strategic gifting initiatives.

10. How does strategic gifting help combat digital fatigue in B2B marketing?

Strategic gifting provides tangible touchpoints that cut through notification overload and digital fatigue by introducing a "surprise factor" outside traditional digital channels. Unlike digital outreach, physical gifts don't compete with digital distractions and create unique memory markers that stand out. Digital outreach cannot replicate the dopamine response triggered by receiving gifts. This makes strategic gifting particularly powerful in today's oversaturated digital environment, helping companies build genuine relationships when prospects are overwhelmed by generic digital communications.

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