Start with your existing payroll provider. If you already use Gusto for payroll, adding benefits within Gusto is the lowest-friction path — your employee data, tax information, and payroll configuration already exist. Adding benefits is a configuration step, not a migration. If you use ADP for payroll, adding ADP's benefits module follows the same logic. Switching payroll providers just to get benefits admin creates unnecessary disruption. Only evaluate standalone benefits platforms (Zenefits) if you do not want to change your payroll setup.
Evaluate your broker relationship before buying software. Ask your insurance broker what enrollment technology they provide. Many brokers include portal access (Ease, Employee Navigator, FormFire) at no cost as part of their services. If your broker provides a functional enrollment portal with carrier EDI, you may only need your payroll provider for deduction sync — saving the cost of a separate benefits platform entirely. This broker-provided technology approach works well for small businesses with stable benefit structures.
Match the platform to your benefits complexity. Gusto handles standard benefit structures well: one or two health plans, dental, vision, and basic FSA/HSA. If your small business offers more complex benefits — multiple plan tiers by employee class, supplemental benefits (critical illness, pet insurance, legal plans), or HSA employer contributions with varying match structures — Zenefits or Rippling handle this complexity better. Overpaying for a platform you do not need is wasteful, but under-buying leads to manual workarounds that defeat the purpose of benefits software.
Consider the admin burden at your specific headcount. For 5-15 employees, any platform handles open enrollment easily. For 30-75 employees, enrollment workflow automation, life event processing speed, and carrier EDI reliability become important. Rippling's automated enrollment triggers are most valuable for companies with frequent hiring — if you onboard 2+ employees per month, the automation prevents missed enrollment windows that create compliance liability. Gusto's enrollment workflow is adequate for companies with less frequent changes.
Check carrier compatibility before committing. Gusto and Zenefits support major national carriers (UnitedHealthcare, Aetna, Blue Cross, Cigna, Kaiser) but may not support regional carriers or specialty plans. If your small business uses a regional carrier (Tufts Health in Massachusetts, Priority Health in Michigan, CareFirst in Maryland), verify that your carrier's EDI is supported before signing up. ADP has the broadest carrier network but at the cost of a less modern interface. Carrier incompatibility forces you into manual enrollment processes, eliminating the main benefit of the software.
Factor in the full cost including open enrollment support. Most benefits platforms handle routine enrollment and changes automatically. But open enrollment — the annual period where all employees review and update their benefits — is the peak stress point. Gusto's self-service enrollment portal handles most of it, but your broker typically guides employees through plan selection. Rippling offers decision-support features at higher tiers. Benefitfocus has the most sophisticated decision engine but at enterprise pricing. For most small businesses, Gusto's enrollment flow plus a broker-led information session covers what employees need.
