Upside Compensation & Benefits

Updated on October 06, 2026

What People Are Saying About Upside

  • Leave & Time Off Breadth: PTO is considered a notable strength, with unlimited PTO, paid holidays, and even a winter break featured in listings. Available information characterizes vacation and sick time as generous and flexible.
  • Healthcare Strength: Health coverage is described as comprehensive, including medical, dental, vision, mental‑health support, and options like FSA/HSA. An employee account notes recent improvements and lower premiums, reinforcing the sense of strong healthcare value.
  • Equity Value & Accessibility: Equity via stock options is positioned as a core component for full‑time hires and is frequently highlighted favorably. This emphasis suggests meaningful perceived value from ownership in total rewards.

Upside's Benefits

Designated President's Club

Offers company equity

Provides home-office stipend for remote employees

Provides pay transparency

Offers childcare benefits

Offers generous parental leave

Provides adoption assistance

Provides an onsite Mother's Room

Provides family medical leave

Provides fertility benefits

Offers abortion travel benefits

Offers dental insurance

Offers Flexible Spending Account (FSA)

Offers health insurance

Offers Health Savings Account (HSA)

Offers mental health benefits

Offers pet insurance

Offers vision insurance

Offers 401(K)

Offers disability insurance

Offers life insurance