How We Pivoted a Failing Campaign Into a Big Holiday Win

It’s the holiday season, which means many companies are conducting some sort of giveaway, contest, or gifting campaign—and every year we challenge ourselves to come up with a unique way to spread holiday joy through gifting. As a gifting company, this is peak season for us and we start planning early.

Following the momentum of our Halloween Spooky campaign, where we built a cute seasonal landing page and sent mini piñatas that look like llama (yes, llama!) vampires to a target list, we wanted to run a delightful holiday campaign to recognize our fellow marketing leaders for their hard work and let them know we’re all in this together. 

But, as the saying goes, “The best-laid plans of marketing teams often go awry” (or something like that). We’re big fans of having multiple backup plans, quickly recognizing a failure and making a pivot — in this case, a pivot led to one of our most delightful campaigns to date.

Read on to get our full blueprint for how we turned our failure into a shining success faster than Clark Griswold lighting up the neighborhood.

The Original Campaign

At Sendoso, we like to drink our own champagne, so as the marketing team, we aim to plan at least one direct mail campaign per quarter. These campaigns support top of funnel demand creation, qualified pipeline generation, and deal acceleration. We have a few simple requirements:

1. Be creative
2. Make people smile
3. Show the impact of gifting and direct mail 
4. Include a shareable element that reinforces our brand marketing work

After traveling to lots of events and speaking to many, many marketing leaders, Kacie, our SVP of Marketing, knew one thing: marketers have moved mountains this year with limited resources. We wanted our community to know that they’re not building alone, and we see the incredible work they’re doing. 

We decided the best way to celebrate marketers in a non-salesy way would be to send them a cute, holiday-themed gift with a personal note of recognition directly from Kacie. After a fun team holiday activity, we wanted to share the creative energy we felt building gingerbread houses together. We hoped the gift of an unexpected gingerbread house would inspire camaraderie, build brand affinity, and make people feel special.

Our Campaign Plan

The campaign consisted of three parts: targeted outreach, the actual gift, and a LinkedIn paid component.

The first step was an email from Kacie recognizing fellow marketers and offering a gingerbread house kit. Besides being very cute, gingerbread houses support the message: “let’s build together” — we marketers aren’t in this alone. The second step was a LinkedIn connection and a personal DM from Kacie following up on the email. 

Upon the recipient accepting the gift, a gingerbread house kit would be delivered to their doorstep with a note from Kacie offering to talk shop and compare notes on 2025 planning. We also included a “surround-sound” approach with LinkedIn ads and a holiday landing page (CTA was a chat with our marketing team) targeting all marketing roles at the account, not just those who were sent a message from Kacie.

The (Failure to) Launch

At launch, we emailed a target list that included slightly over 300 marketers. This was the beginning of holiday season, with people just returning from Thanksgiving in the U.S. and all marketing teams racing to get ahead before businesses (and meetings) pause until January. Inboxes were chaos and marketers were busy. We received zero email responses, which was disappointing but didn’t immediately throw us off track. 

The next day, Kacie sent LinkedIn connect requests to half of the list, attempting to engage via a more direct and personal channel. 23 accepted the connection. More disappointment — the campaign was moving much more slowly than planned, but we pressed on. 

In addition to Kacie DMing those new connections, we decided to challenge our assumption that InMail was a bad way to reach this group by sending 50 of them as a test. To no one’s surprise, we were right.

The results from the DMs were surprising to us—some people assumed it was a pitch, and most just didn’t respond. Of the few responses, a few politely declined the gingerbread house, a couple of people said thanks and accepted it, and one marketer had a great call with Kacie and then referred us to a prospect.

We also saw one conversion from our LinkedIn ads, but it was a potential partner, not a prospect.

We assessed the numbers so far:

• 300 emails sent, 0% response rate
• 152 LinkedIn connections sent, 23 (15%) converted to connections
• 50 InMails sent, 2% response rate

After two days of running this campaign, we quickly realized it wasn’t working. We weren’t 100% sure if it was the gift, the messaging, or the timing of the season (or all of the above), but we weren’t getting the reaction we had expected. Instead of giving up and writing it off as a failure (which it was) or continuing to bang our heads against the wall by doing the same thing with different lists (a traditional way of thinking), we made the call to pivot. We had a backup plan inspired by a previous “gift it forward” coffee campaign, with additional inspiration from a very unlikely source.

Here comes…Chewy Claus?

If you’ve ever heard Katie Penner, our Head of Sender Relations, talk about her favorite brands, you’ve heard her mention Chewy, the pet supply company with a fantastic reputation for putting customers and their fur babies first. When we had originally brainstormed holiday campaign ideas, she mentioned their adorable holiday campaign, which lets pet parents submit a “Letter to Chewy Claus” on behalf of their pet.

Their landing page was simple: a customized form that allows the submitter to “write a letter to Chewy Claus” and choose what their pet would like, including toys, treats, and even a donation to shelters. After submitting, pet parents get an email letting them know their pet’s wish list has been sent to Chewy Claus, and they just might get their wish granted.

We loved this idea, but had originally feared it might be too big of a lift for our small but mighty team to build to our standards. Now, with our original plan floundering, we realized that reaching out directly to marketers we didn’t yet know, even with a personal message and cute gift, wasn’t nearly as powerful as enabling our community to acknowledge each other. 

We thought: what do we have to lose? We’ve already built the foundation for a Chewy style holiday campaign — let's repurpose our assets, go bigger and do Chewy Claus our way for our GTM community. 

Our previous virtual “gift it forward” Thanksgiving coffee campaign allowed folks in our community to send coffee gift cards to others as an expression of gratitude and encouraged recipients to “pay it forward” by keeping the chain of gratitude going. It was a hit — making it easy and accessible for people to show appreciation for those they care about is a no-brainer for us, and it resonated with our audience. Sometimes you don’t need to reinvent the wheel. We knew we could do that again, even better.

Building the Sendoso Elves Workshop

We wanted to make it easy and fun for our GTM community to send a letter to the Sendoso Elves, nominating colleagues and recognizing the hard work they’ve put in over the past year. We already had holiday assets ready to go: a landing page, the ad images, and a form that just needed some work to become a dynamic “letter to the Sendoso Elves.” The pivot was spearheaded by Austin, our Head of Growth. Here’s the rundown of everything that went into it.

Landing Page

We duplicated and updated the landing page using our original holiday page template and added a dynamic “letter writing” form.

The form’s dynamic fields include two text fill-ins for the nominee’s name, nominator’s name, a drop-down menu to choose what type of gift the nominee might like (treat, self-care, something for their workspace, plant, or surprise), and a long-form text box for the nominator to fill in why they felt the nominee deserves a gift.

Time spent: ~3 days; QAing form took the longest

Creative assets

Our designer repurposed the graphic we were already using for our LinkedIn ads to match the “nominate a colleague” language. This way, we could include a shareable image in the email nominees received.

He also created additional LinkedIn assets to help us spread the word:

• Holiday-themed Sendoso page profile picture
• Elf-themed profile photo template for our team
• LinkedIn banner images with the landing page URL and “nominate a colleague” language
• Promo image for the team to share on LinkedIn

Time spent: 1 day

‍Emails‍

We needed three emails: one to notify nominees that they had been nominated, one for the nominator to confirm their submission, and one for the actual gift send. With the help of a well-trained ChatGPT, Austin and the team were able to spin those up with a bit of tweaking really quickly.

For the gift send email, which began as a manual process so we could get started as quickly as possible, Austin created a template that included the nominee’s name, the nominator’s name, the text from the “Why did you nominate this person?” section of the form, and the link to allow the nominee to confirm the best address for their gift.

Time spent: ~2 hours

Tech integrations

To get this out the door quickly, we took advantage of Zapier pretty heavily. Austin set up zaps to:

• Push the nomination form information into a Slack channel
• Push nomination form information into a Google Sheet
• Create a cute elf image that fills in the nominee’s name, photo, and who nominated them (we took inspiration from Orum’s Outbound at Inbound fire truck campaign)

Marketo also played a role in automating the emails sent to the nominator and nominee after the form submission.

When we launched the campaign, we manually copied and pasted the names, gifts, and images into the email templates. Then we built a Clay table to weave this all together and add some automation magic.

Time spent: 1 day

All in all, this entire campaign was built in less than a week, which included a weekend. Yep, you read that right: less than a week. We were able to repurpose many assets we already had from the original campaign, which made this a much lighter lift for us — the definition of work smarter, not harder.

Initial Results

As the thoughtful elf letters started to roll in, we knew we had made the right call on this pivot. Overall, we’d call this campaign a success, and we’re not done yet! So far, over 330 letters have been sent to the Sendoso elves — that’s 330 people who have recognized others for their incredible work done in 2024. What’s especially heartwarming is that people who received the nomination emails checked out the campaign and nominated others, so we know it’s resonating in the way we had hoped.

We’ve sent out over 300 gifts, seen many people share their fun elf images on LinkedIn, and received tons of positive feedback from the GTM community — some from customers and prospects who’ve been inspired to run similar campaigns, some from people just observing and appreciating the campaign. That’s a massive win for our brand and for us.

If We Can Do It, You Can, Too

This reminded us that a) we don’t always have to come up with brand new ideas; it’s smart to repeat and build on successful past campaigns, b) sometimes a slightly heavier lift is worth the effort, especially if you can find ways to work smarter. 

There are definitely advantages to large teams with huge budgets and many available resources, but we’re proud of our lean, resourceful team of seven people (which includes 3 BDRs). We were able to pivot a failing campaign in a matter of days and arguably make it exponentially better than our original idea.

That’s why we wanted to share this playbook: Creating fun, engaging campaigns doesn’t have to be complicated, expensive, or require huge teams of people. Creative minds working together (and having a good time doing it) can do amazing things, too.

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