Work anniversaries are more than just dates on a calendar — they’re an opportunity to show appreciation, strengthen employee engagement, and reinforce your company culture. But as your team grows or becomes more distributed, keeping up with each milestone can quickly become a logistical headache.

That’s why we’ve built Work Anniversary Automation into PerkUp — so you can automatically celebrate every employee, every year, without losing the personal touch that makes those moments meaningful.

Here’s a look at what this new feature can do.

✨ Custom Automations for Every Team

No two organizations celebrate the same way — and that’s exactly why we’ve made customization the foundation of our Work Anniversary Automation.

With PerkUp, you can set up custom automation rules that define how different groups of employees are celebrated. These rules can be based on things like:

• Tenure: Increase the gift budget or offer more premium options as employees hit key milestones (e.g., 1 year, 3 years, 5 years).

• Location: Send region-specific swag or gifts to make sure employees in different countries get items that are relevant and culturally appropriate.

• Department: Tailor the gifting experience for different teams — for example, send branded gear to engineering while offering home office upgrades to remote-first departments.

These rules are flexible and easy to stack. Want to send a $100 gift to employees in the US who are hitting their 3-year anniversary and work in Marketing? You can do that — and much more. Once your rules are set, PerkUp automatically handles notifications, gift delivery, and tracking.

👤 Manager Personalization (Without the Follow-Up)

While automated gifting is a huge time-saver, the real impact comes from making it feel personal — especially when recognition comes from someone employees work with every day.

To help with this, managers now get a notification ahead of each direct report’s anniversary, giving them the chance to personalize the message that will be sent along with the employee’s gift.

Here’s how it works:

• Your company sets a default anniversary message — this is what’s sent if the manager doesn’t make any changes.

• The manager can easily edit and personalize the message in just a few clicks.

• That message is included in the gift email the employee receives, creating a moment that feels more thoughtful and authentic.

This helps strike the perfect balance between automation and human connection — all without your HR team needing to remind managers or chase down messages.

🎁 Give Employees the Power to Choose

Not every employee wants the same gift — and guessing wrong can turn a nice gesture into a missed opportunity. That’s why we’ve built gift and swag collections into our Work Anniversary Automation.

Instead of sending a one-size-fits-all item, you can let employees choose from a curated set of gifts that you define. For example, for a 5-year anniversary, you might offer a choice between:

• A premium branded backpack

• A cozy, high-quality sweatshirt

• A stainless steel PerkUp tumbler

Employees pick the item they actually want, which makes the experience more rewarding and reduces waste. You can also tailor collections by tenure, region, or department — giving you even more control over the experience without increasing your team’s workload.

This approach is especially useful for global teams or milestone anniversaries where a more elevated gift experience is expected.

💬 Celebrate in Slack — Automatically

In fast-moving teams, it’s easy for milestones to go unnoticed — even when they matter. With Slack automations, you can bring work anniversaries into the spotlight in the channels your team uses every day.

You have full control over how these celebrations appear:

• Choose to post a daily or weekly roundup of anniversaries in a Slack channel of your choice (e.g., #celebrations, #team-updates).

• Or opt to highlight each anniversary individually as it happens — perfect for smaller teams or when you want each person to get their own moment.

Each message includes the employee’s name, work anniversary, and a message from your company (or their manager, if personalized), making it easy for coworkers to join in the celebration and add their congratulations.

It’s a simple way to reinforce your company culture and make sure everyone feels appreciated — even on the busiest days.

Ready to Automate Your Anniversary Gifting?

You’ll find the new Work Anniversary Automation feature in your PerkUp dashboard under Automations > Work Anniversaries.

From there, you can:

• Set custom automation rules

• Define gift or swag collections

• Enable manager personalization

• Turn on Slack notifications

Once it’s live, PerkUp takes care of everything — ensuring every employee gets recognized in a meaningful, personalized way, no matter where they are in the world or how big your team gets.

Have questions or want help setting it up? Reach out to your Customer Success Manager or check out our Help Center.