This guide shows lean teams how to decide on open enrollment outside help versus handling enrollment in-house before January coverage starts. Nearly 70% of entrepreneurs in a U.S. Chamber of Commerce and JustWorks survey of 759 businesses said they need help running their programs and wish they had outside support in structuring, operating, and budgeting them, according to RALI’s report on the poll. That report says premium increases to all companies this year are slated to surpass 9%, which makes the choice urgent.
Updated November 11, 2026
Key Takeaways
- Nearly 70% say they need help running benefit programs.
- Premium increases to all companies this year are slated to surpass 9%.
- Chamber: more firms report offering health insurance, 46% up from 41%.
- Medicare Part D notice is due before October 15.
What should you check first?
Check cash and capacity before the brochure. The Q3 2026 Small Business Index is 70.5. Seventy-two percent of small businesses are comfortable with cash flow, and 54% name inflation as their biggest challenge. Forty-five percent say they lack time or resources to focus on employees as they would like.
Most small businesses run on a January 1 plan year, so OneDigital’s enrollment guide says renewal decisions need to happen in October. Work backward: plan review in September, communication in October, enrollment closes in November. If enrollment closes November 15, the guide’s sample internal cutoff is November 10.
When does open enrollment outside help make sense?
Keep the two survey findings separate. The Chamber executive summary says 67% of small-business decision makers wish they had outside help when it comes to offering employee benefits. RALI’s nearly 70% figure is about needing help running programs and wishing for outside support in structuring, operating, and budgeting them. That desire stood at 75% among Gen Z and millennial owners, 64% among Gen X, and 54% among boomers.
Bring in a broker, benefits advisor, or PEO when these conditions show up:
- No dedicated HR team; an owner, office manager, or finance lead inherited the benefits folder.
- You cannot review utilization and communicate before rates lock.
- You need level-funded plans, ICHRAs, or reference-based pricing compared before you sign.
- One person covers HR, payroll, and compliance. A PEO can pool firms for large-group rates and bundle administration, and it is not right for everyone.
- Compliance is the weak spot. Talk with an advisor before enrollment opens.
Ask your broker for right-sized tools. If payroll is part of the load, see how embedded payroll is reaching small firms.
How do rising premiums change the budget call?
Do not start with the rate alone. OneDigital says the better question is whether the plan still works. Premiums are projected to rise a median of 11% in 2026, the steepest increase in over 15 years. Increases to all companies this year are slated to surpass 9%, RALI reports, and they hit small businesses harder.
Gusto data cited by RALI shows employee medical costs up 31% since 2022, to $8,743 per worker. Firms with two to five people endured 35% premium hikes and now pay about 6% more than businesses with 25 to 50 employees, while inflation squeezes small-business margins.
| Benefit | Earlier share | Latest share |
|---|---|---|
| Health insurance | 41% | 46% |
| Paid vacation days | 30% | 40% |
| Dental and vision | 21% | 31% |
| Retirement plans | 22% | 27% |
The Chamber summary reports these as the share of small businesses offering each benefit, with health insurance up from 41% in Q2 2025. RALI uses the same percentages as the share of workers or staff covered or participating.
Stevie Straka, vice president of people at Blumira, said in a report on the USCC survey, “Health insurance premiums climb nearly every renewal cycle, often outpacing general inflation.” She continued, “(T)hat forces a tough annual trade-off between absorbing rising costs, shifting more of the burden to employees, or scaling back coverage.” Make that call before October.
How do you run enrollment if you stay in-house?
- Calendar the window and plan two to three touchpoints: an announcement, a plan-detail reminder, and a deadline reminder, via Slack, a group text, or a meeting, not one email.
- Review utilization reports if the carrier provides them, and benchmark value, not only price.
- Drop email threads and spreadsheets. Use timestamped electronic elections and waivers, automated reminders, and a clean carrier export or feed.
- Send a two- or three-sentence summary per plan, record a 20-minute Q&A, and show the employee’s share, not the full premium.
- Refresh the Summary Plan Description before enrollment if benefits changed and it is not current.
Which notices still apply before coverage starts?
Small size is not an exemption. Distribute the SBC, the CHIP notice, the WHCRA notice, and the Medicare Part D creditable coverage notice at or before enrollment. The Part D notice is due before October 15. Log each notice, its trigger, and its deadline.
Federal COBRA kicks in at 20 employees, so growth can change the rules. If notices and the October decision will slip, call a broker or advisor before the window opens.
Frequently asked questions
When should January 1 plans lock renewal decisions?
OneDigital says most small businesses on a January 1 plan year need renewal decisions in October, with review in September and enrollment closing in November.
What notices have to go out before open enrollment?
Send the SBC, CHIP notice, WHCRA notice, and Medicare Part D creditable coverage notice at or before enrollment. The Part D notice is due before October 15.
Can a small team run open enrollment without an HR department?
Yes. OneDigital says you need a clear process, the right tools, a partner for support, and enough lead time, not a full HR department.
Do benefits still help small employers keep staff?
Around 80% of small business owners in the survey said employees are satisfied with the current offering. Lincoln Financial data cited by RALI finds 74% of employers who offer voluntary benefits cite positive effects on recruitment, retention, and performance.
