Employee Milestones: A Guide to Work Anniversaries and Years of Service

Employee Milestones: A Guide to Work Anniversaries and Years of Service

Employee work anniversary celebrations and gifts show employees you see and value their contributions to your company. Our guide will help you plan meaningful, creative, and budget-friendly celebrations!

Employee Milestones: A Guide to Work Anniversaries and Years of Service

Every year an employee stays with your company, their institutional knowledge, experience, and contributions grow. Are you rewarding their loyalty with a meaningful work anniversary celebration in return? 

Service anniversaries are a great time to show employees how much you value their work and boost your overall employee experience. But coming up with the perfect way to celebrate these milestones can be overwhelming. We’ve curated ideas for one-year anniversaries, five-to-ten years, and beyond so you can pick the perfect milestone marker that will be meaningful for your employees. 

Close up of a group of coworkers having a celebration in their office

The Importance of Work Anniversaries

Celebrating employees who stay with your company shows them you recognize and value longevity and loyalty. It sets the tone for your ongoing relationship and encourages them to stick around for the long haul. 80% of companies have some sort of service award program, so if you don’t already have one, you’re falling behind the organizations that do.  

And with the rise of remote and hybrid work, recognizing and appreciating employees is even more critical—64% of employees think so, at least. Work anniversaries are also the point at which many employees start seriously job hunting, particularly after the first, second, or third anniversary. Getting the recognition and celebration right can have a serious impact on your retention rate. 

Of course, anniversaries are only one component of a strong overall employee recognition program—you definitely need to recognize and reward employees for their contributions throughout the year. But marking these milestones with care and thought is meaningful for your employees, and for your organization as a whole. 

Celebrating and recognizing an employee’s work anniversary can come in many forms. We’ve put together some ideas for how to make these anniversaries feel special and tie into your employee engagement efforts. 

Celebrating the First-Year Work Anniversary

The first year of an employee’s tenure at your company is a major milestone. They’ve settled into the organization, learned what they need to succeed in their role, and they’ve become contributors instead of trainees. So you should celebrate accordingly! 

In the past, many companies waited to celebrate workers until they hit at least five years with the company. While those milestones are important, employee recognition shouldn’t wait until they’re years into their tenure. With millennials staying only an average of 2.3 years in a company, those five-year rewards will miss a major portion of your employees, so start recognizing them from the very beginning. 

Here are our top three suggestions for that perfect first work anniversary gift:

A Handwritten Note 

Meaningful work anniversary celebrations don’t need to break your budget—sometimes the most heartfelt recognition is free. Receiving a thoughtful, handwritten note from a manager or leader that goes into the many contributions the employee has made in their first year shows deep appreciation and effort. 

Plus, the employee now has a tangible reminder of their great work and value to the company in this personalized message. They can hang it up in their office and read it when they need a pick-me-up. 

close up of a person's hand writing on a pink sticky note attached to a wall of sticky notes

Social Media Shoutouts 

Public recognition is a powerful motivator for many people—and social media offers you an easy and meaningful way to offer that recognition. Posting on LinkedIn or wherever your company and employees are most active gives employees a public thank you for their first year with your company. It’s a great way to spotlight employees for their contributions and loyalty. 

These recognition posts can also show your larger community how your company has grown, and how you celebrate the people who stay with you and recognize their hard work. Just be sure to make the recognition post thoughtful and customized with their accomplishments to make the maximum impact. Copy-and-paste posts won’t have the same meaning. 

screenshot of an employee shout out posted by MountainSeed on LinkedIn
Cooleaf partner, MountainSeed, recognized Andy Reisser for 6 years of service with a special spotlight posted to their company LinkedIn!

Customized Company Swag 

Allowing your employees to pick out some fabulous branded swag can be a great first anniversary option—if it’s done right. If they’re left scrounging through a pile of generic t-shirts that don’t fit them, or some leftover tote bags from a conference, that’s not a meaningful experience of appreciation or an incentive to stick around. 

However, if you offer them customized choices that are thoughtful or high-end, like a comfortable commuting backpack or a personalized jacket with your company logo, employees can pick what calls to them and feel appreciated and seen. Plus, they can show off their employment at your company, giving you some extra brand building as a bonus. 

Creative Ways to Celebrate 5 to 10-Year Work Anniversaries

The first work anniversary is an exciting milestone, but it’s critical to celebrate your employees on a regular basis even when they’re not new. The five and ten-year work anniversaries are particularly important in an employee’s life, so don’t miss the chance to celebrate them in a customized and meaningful way!

Career Planning Session 

When an employee hits an important milestone in their career, like 5 or 10 years with your organization, they might consider where their career has taken them so far and where they’d like to go next. Offer them the support and direction they might need for the next step with an intensive career planning session! 

This is a big milestone, so be sure this session isn’t the usual annual career chat with their direct manager but something more targeted and exciting. You could bring in an outside career coach, or offer a sit-down session with someone on the leadership team, or ask an ΗR team member to help—what matters is how this person can help the employee think big about their next phase in the company. 

close up of two coworkers planning finances together

Charitable Donations 

Making a donation in the name of your employees when they have a significant milestone anniversary is a meaningful way to mark these high points. You’ll need to check with employees to see which charity they’d like to support so the gift is personalized—giving to the same charity for everyone simply doesn’t have the same impact. 

And these donations can reaffirm to employees that their personal values and causes matter to your organization. Plus, they help people in need—a real win-win—instead of cluttering up their homes with yet another lavish but impractical gift from a catalog. 

screenshot of different charitable donation options in Cooleaf platform
Rewards points on Cooleaf can be used for donations to The Humane Society, First Responders First, and many more!

A Team Celebration 

You can calibrate these celebrations to your individual employees and their preferences, but some sort of gathering for their special day is often very welcome for anniversary recognition. You can host a lovely in-office lunch, a remote happy-hour gathering, an afternoon at the cupcake store near the office, or an hour sharing their favorite stories and funniest moments in their role so far—as long as it’s what the employee would enjoy, it’s fair game. 

And these gatherings can be a great opportunity for team bonding as well! Having coworkers come together to celebrate service anniversaries builds a stronger company culture as they form stronger bonds and see that your organization rewards employee loyalty. 

Time Off 

Giving your longer-tenured employees an extra day off to celebrate their work anniversaries offers a tangible and meaningful way to reward them for all the time they’ve put into your organization. 

Of course, to be maximally effective, the employee must be allowed to fully disconnect from work on their day off—no check-ins, no emails, no quick questions, just rest and relaxation. And it should be in addition to, not a replacement for, the time off they already receive as part of their employee benefits.


If you’d really like to go above and beyond, you can offer long-term employees a sabbatical option once they mark five years at your company. These options are growing in popularity as many employees would love a longer break from work to focus on something else. Instead of taking a break by quitting their current role, your organization can retain them by offering them the chance to step away from work for a bit and return refreshed. 

In fact, sabbaticals are more than just a great recruiting and retention tool—they have other benefits for your organization, such as allowing less-experienced employees to gain hands-on experience in a larger role while they cover for your seasoned veterans. 

a woman is napping in a hammock outdoors

Beyond the Celebration: How Work Anniversaries Contribute to Employee Retention and Engagement

Recognizing employee work anniversaries is a critical part of your employee rewards and recognition program. These celebrations and gifts aren’t just valuable because of the dollar amount involved, but because they show employees you see and value their contributions to the company. That’s beneficial for retention, for employee engagement, and for satisfaction as well. 

Looking for a simple but powerful way to make your employees’ work anniversaries even more special? With Cooleaf, you can celebrate them with social posts; a customizable rewards catalog with options like tech gear, gift cards, company swag, days off, and charitable contributions; and automated reminders so you never miss a service anniversary. Try it and see for yourself!

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