Square Compensation & Benefits

Updated on August 31, 2026

What People Are Saying About Square

  • Healthcare Strength: Medical coverage offers multiple Aetna and Kaiser options plus dental (Delta Dental) and vision (VSP), and includes gender‑affirming care; Lyra provides up to 16 no‑cost therapy or coaching sessions annually for employees and eligible dependents. For the Aetna HSA plan, the employer contributes enough to cover half the deductible.
  • Parental & Family Support: Paid parental leave is highlighted for U.S. roles at up to sixteen weeks, complemented by paid medical and caregiving leave. Fertility via Progyny (for Aetna enrollees) and adoption/surrogacy support apply regardless of medical enrollment.
  • Equity Value & Accessibility: Employees receive equity grants and can participate in an Employee Stock Purchase Plan at a stated 15% discount.

Square's Benefits

Offers company equity

Offers employee stock purchase plan

Offers performance bonuses

Provides pay transparency

Provides relocation assistance

Offers childcare benefits

Offers generous parental leave

Provides adoption assistance

Provides family medical leave

Provides fertility benefits

Offers abortion travel benefits

Offers dental insurance

Offers Flexible Spending Account (FSA)

Offers health insurance

Offers mental health benefits

Offers vision insurance

Offers 401(K)

Offers disability insurance

Offers life insurance

Provides 401(K) matching