A tenure milestone is an increase to an employee's time off entitlement based on how long they've worked at your company. For example, you might give employees 15 days of PTO in their first five years, then bump that to 20 days once they hit their ten-year anniversary.

Once an employee reaches a milestone, that new entitlement becomes their baseline going forward. It stays in place until they reach the next milestone.

You choose when an employee's new entitlement kicks in. There are two options:

On the employee's anniversary date

The new entitlement starts the day the employee actually hits the milestone. If someone's three-year anniversary falls on June 15, their higher balance starts June 15, no matter where that falls in your plan year. These can be prorated or allocate the full amount.

At the start of the plan year

The new entitlement starts on the first day of your next entitlement year, even if the employee's actual anniversary falls somewhere in the middle of it. This keeps every employee's balance change lined up with the same reset date.

You also choose how much of the new entitlement an employee gets in the year the milestone happens:

Sarah joins on April 1, 2023. She hits her three-year milestone on April 1, 2026. Your plan year runs January to December.

Example 1: Full award

Milestone set to anniversary date + full award.

Sarah's balance jumps straight from 15 to 20 days on April 1, 2026, the exact day she hits three years. She gets the entire 5-day increase at once, with no partial amount and no waiting for the next plan year.

Example 2: Prorated award

Milestone set to start of plan year + prorated.

Sarah's milestone falls on April 1, 2026, which is 9 months before the next plan year starts (January 1, 2027). Instead of waiting the full 9 months for her increase, she gets a prorated slice of it added to her existing balance for the rest of 2026:

On January 1, 2027, when the new plan year starts, Sarah moves to the full 20 days.

Note: Once a milestone takes effect, it becomes the new baseline. Employees don't drop back to their old entitlement. Each new milestone builds on top of the last one.

Say your Tenure group awards 5 extra days at the 5-year mark, and a separate custom group awards 3 extra days to employees with 10 years worked in Greece.

An employee with 5 years of tenure and 10 years worked in Greece qualifies for both groups at once. Because the awards come from two different groups, they stack: 5 days plus 3 days equals 8 extra days added to the base entitlement.

You set up milestones inside your time off policy. For each milestone, you'll define:

You can set up as many milestones as your policy needs, so an employee's entitlement can keep growing at 3 years, 5 years, 10 years, or whatever schedule fits your company.

Inside your policy, check the box to grant additional days on milestones.



Pick whether awards happen at the start of the policy year or on the event date (the employee's actual anniversary), then add a milestone group. In this example, employees get 1 extra day at their 1-year mark, bringing their total to 16 days.

Add as many tenure milestones as your policy needs. Here, employees also get 2 extra days at 5 years (17 total) and 5 more at 10 years (20 total). Each milestone REPLACES on the one before it.

Beyond standard tenure milestones, you can create a separate group for one-off or criteria-based adjustments, like a named employee or a custom field such as years worked in a specific country. These STACK on top of the tenure awards.