Bring a Little Love to Work this Valentine’s Day

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Madeline Chizmar
Madeline Chizmar
3 mins
Bring a Little Love to Work this Valentine’s Day

A simple Valentine’s tradition that stuck with me

When I was a Director of People Ops several years ago, Valentine’s Day was one of our biggest work traditions. Every year, our People Team would spearhead a Valentines exchange.Everyone at the company had a week to write anyone else at the company lighthearted Valentine notes. These were sometimes funny, sometimes sincere, but always kind. No pressure and no formality required – just small moments of acknowledgement that made people smile.

It appeared so simple (but took a ton of work behind the scenes). And it worked! We didn’t put a limit on how many cards anyone could send. To our amazement, some folks made it a goal to send a card to every employee at the company (our CEO, Scott Wolfe, was one of these high achievers). This simple tradition came up often as a bright spot in the employee experience – at town halls, in anonymous feedback, during exit interviews, and more.

People felt seen and teams felt closer. We always strived to make sure folks had a digital copy and a physical one they could keep on their desk to remember how appreciated they were. Some folks still tell me to this day they have their cards at their desk as a reminder.

This silly tradition became something deeply human and surprisingly meaningful.

This year at CultureBot, we decided to bring that spirit back. Just with a fun automated twist.

How we’re celebrating Valentine’s Day at work this year 💌

Instead of traditional shoutouts, we created temporary Valentine’s Day Shoutout Types inside CultureBot.

For one week only, teammates can send Valentine cards instead of shoutouts to share appreciation, inside jokes, and acknowledgment of each other with just a dash of absurdity.

It keeps appreciation fresh, playful, and seasonal without changing any long-term setup or a time-intensive engagement campaign.

And yes… we made Muppet Valentines.

Why this works (beyond just being fun and cute)

Traditions like these create:

  • Moments of connection
  • Low-pressure recognition and appreciation
  • Shared team culture
  • Psychological safety
  • Energy during slower or stressful seasons (such as the start to a new year)

We know how important engagement programs are for remote and hybrid workspaces, and this type of program offers a temporary, lightweight, and optional way for employees to interact with each other outside of the norm.

How to create a temporary Valentine’s shoutout

You can do this on your own to celebrate Valentine’s Day at work, or you can set this up in CultureBot in just a few minutes:

Step 1: Create a new shoutout type

  • Go to Admin > Shoutouts Settings > Customize
  • Add new customer shoutout: Name it something Valentine related

Step 2: Customize

  • Add a seasonal icon, heart emoji, or custom background (templated options below)
  • Optional: change color or description to give context
  • Keep the tone fun and light! You can add jokes or make it feel a bit more on brand for your company

Step 3: Announce it as temporary

  • Announce it as a limited-time shoutout
  • Run it for 1-2 weeks around Valentine’s Day

Step 4: Encourage participation

  • Post examples
  • Lead with a few yourself (or better yet, get a few executive team members to send the first few)
  • Keep it playful

That’s it! We’re here if you need any help. Send a Valentines email to support@getculturebot.com for help or brainstorming.

Our Muppet Valentines (steal these templates for your own Valentine’s Day at Work) 💘

Here are a few templates we created for inspiration and joy. Feel free to use these in your own Valentine campaign. You can use these as a “full background” option in CultureBot, or create your own! I used Canva to create mine, size 1500px x 700px.

(Yes, this may be the most important engagement strategy we’ve ever shipped.)

Try Valentine’s Day at work with your team

To recap, if you’re looking for a simple way to spark connection:

  • Create a temporary Valentine shoutout
  • Keep it optional and fun
  • Let personality show

Small moments build real culture, and sometimes keeping it silly is exactly what your team needs.

💛 Happy Valentine’s Day from CultureBot.

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Scott G. Wolfe Jr.
Nate Budde
Martin Roth
Madeline Chizmar
Madeline Chizmar

Co-Founder

Madeline Chizmar is Co-Founder of CultureBot and co-founder of Brightspot People. With a career spanning Procore, Levelset, and stellar, she’s passionate about building connected, high-performing teams through thoughtful people operations and culture change.
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