Open Enrollment
Open Enrollment for 2027 benefits runs from November 2–13, 2026.
Open Enrollment is your once-a-year opportunity to review current benefit elections and make changes for next year:
- Switch medical plans
- Add or remove dependents
- Enroll or re-enroll in Flexible Spending Accounts (FSA), a Health Savings Account (HSA), and a Commuter Account
- Sign up for voluntary benefits
If you do not wish to make changes, you do not need to log in to the Five9 Benefits Hub unless you are a Cigna OAPIN member. Current benefits generally carry over to 2027, except FSA and/or Commuter Account, HSA, and the Benefit Waiver credit. Cigna OAPIN members must select a different medical plan to avoid waived medical coverage.
Need Help?
Call (925) 658-1569 if you have questions about your benefits or how to enroll.
How to Enroll
When you’re ready to enroll or make changes, visit the Five9 US Benefits Hub:
- Go to your Okta portal.
- Click UKG (UltiPro).
- Go to Myself > Benefits > Manage My Benefits.
- In the Five9 US Benefits Hub, click the Open Enrollment task under “My Benefits” and follow the prompts.
Open Enrollment changes take effect January 1, 2027. For assistance with health and welfare benefits, reach out through the Scout app; it opens a Benefits & Retirement Freshservice ticket.
Documentation for Dependents
If you’re enrolling dependents for the first time, you may need to provide:
- Marriage certificate
- Birth or adoption certificate
Supplemental Life and AD&D
If you previously waived coverage and now want to enroll in or increase Supplemental Life and AD&D coverage for yourself or your spouse, you must complete Evidence of Insurability (EOI).
New hires may enroll up to the guaranteed issue amount without EOI. EOI is required for any amount above the guaranteed issue.
Additional Step for Recent New Hires
If you’re hired during (or after) Open Enrollment, you’ll need to enroll twice: first for the current plan year, then again for 2027.
What’s New and Changing in 2027
Per Paycheck Plan Costs
2027 Medical Rates
Cigna HDHP
- Employee Only: $0.00
- Employee and Spouse/DP: $214.17
- Employee and Child(ren): $142.77
- Employee and Family: $374.79
Cigna PPO OAP
- Employee Only: $0.00
- Employee and Spouse/DP: $321.25
- Employee and Child(ren): $214.17
- Employee and Family: $562.18
Kaiser HMO (CA Only)
- Employee Only: $0.00
- Employee and Spouse/DP: $189.35
- Employee and Child(ren): $157.79
- Employee and Family: $315.57
2027 Dental Rates
Cigna Dental PPO
- Employee Only: $0.00
- Employee and Spouse/DP: $5.00
- Employee and Child(ren): $5.00
- Employee and Family: $10.00
2027 Vision Rates
VSP Vision Base
- Employee Only: $0.00
- Employee +1: $2.50
- Employee +2+: $5.00
VSP Vision Buy-Up
- Employee Only: $3.01
- Employee +1: $8.25
- Employee +2+: $14.34
Contribution Limits
Flexible Spending Accounts (FSA)
In 2027, you can contribute up to:
- Health Care or Limited Purpose FSA – $3,500 (projected)
- Dependent Care FSA – $7,500
You can carry over up to $680 of unused Health Care & Limited Purpose FSA funds into 2027, and up to $700 (projected) from 2027 into 2028.
Health Savings Account (HSA)
Five9 contributes $75 semi-monthly ($1,800 annually) to the HSA for an employee enrolling only themselves and $120 semi-monthly ($2,880 annually) to the HSA for those enrolling one or more dependents if you are enrolled in the Five9 HDHP.
Commuter Benefits
In 2027, you can contribute up to:
- Parking – $350 per month (projected)
- Public Transportation – $350 per month (projected)
Review These Details Before You Enroll
Click the boxes below to review important benefit notes for 2027.
Cigna OAPIN
The Cigna OAPIN plan will no longer be offered as of January 1, 2027. If you and your dependents are currently enrolled, you must select a different medical plan during Open Enrollment, such as Cigna HDHP, Cigna PPO, or Kaiser HMO (CA Only). If you do not elect a new plan, medical coverage will default to Waived in 2027.
Cigna HDHP
The Cigna HDHP deductible for individuals (and individuals within the Employee + Spouse, Employee + Child(ren) and Family coverages) will increase by $100 from $3,400 to $3,500 due to IRS regulations.
Medical Plan Rate Increases
Cigna and Kaiser medical premiums will increase January 1, 2027 due to claims experience and general healthcare inflation. Semi-monthly medical contributions will increase to partially offset these costs. Five9 will continue to cover the full cost of employee medical coverage and hold dependent medical cost shares at 65%. Employee contribution amounts for all other coverages will remain unaffected.
Long-Term Care Insurance
Long-term care insurance has a separate enrollment process. Enrollment runs concurrently, but you must enroll at EnrollForLife.com, not the Five9 Benefits Hub, by November 13, 2026. A medical questionnaire is required, except for new hires after May 18, 2026 who qualify for guaranteed coverage up to plan limits. Read the Long-Term Care Insurance knowledge article for details.
Ready to enroll?
Before you enroll, see what’s new and changing for 2027. There may be changes that are important to you.
You have until 11:59 p.m. ET on November 13, 2026 to enroll or make changes. If you do not wish to make changes, you do not need to log in to the Five9 Benefits Hub unless you are a Cigna OAPIN member. Current benefits generally carry over to 2027, except FSA and/or Commuter Account, HSA, and the Benefit Waiver credit. Cigna OAPIN members must select a different medical plan to avoid waived medical coverage.