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Hopper — Unlimited PTO Jobs

Montreal-based travel app that predicts flight and hotel prices, and sells the fintech products — price freeze, cancel-for-any-reason — that let travellers de-risk a booking.

5 day weekUnlimited PTOMontreal, CanadaEnterprise (1000+)Fully Remote

About Hopper

What is Hopper?

Hopper is a travel app built on prediction. Its algorithms "process and archive trillions of data points" and analyse "over 30 billion price points in real-time" to tell travellers whether to book now or wait. Sitting on top of that is a fintech layer — Cancel for Any Reason, Change for Any Reason, Leave for Any Reason, Disruption Assistance — which Hopper says has "exceptionally strong CSAT because the terms are always clear, and customers receive instant, no-questions-asked resolutions."

That layer is now most of the business. Through HTS (Hopper Technology Solutions), its B2B division and "more than 75% of the business," partners including Capital One, Air Canada, Uber, CommBank and Nubank distribute Hopper's fintech products and travel inventory on their own channels. Hopper says it has "raised over $750 million of private capital."

Where will I work?

Wherever Hopper hires. "We're a fully remote company with team members all around the world," and the careers page dates it precisely: "Since ditching our offices in 2020, we've expanded our team around the world." Every current posting is marked 100% remote, spanning the US and Canada — Canadian roles are published in French as well as English — plus the UK, Ireland, Spain, the Netherlands, Brazil, Mexico, Argentina and the Gulf. Read the fine print: a few non-core markets are offered as independent-contractor engagements rather than employment, and those postings say so explicitly.

What is the Hopper team like?

Small teams with unusually wide remits. Hopper runs a "single-threaded ownership (STO) model" and is direct about the bargain: high standards in exchange for "Autonomy — you will have actual decision making authority," "Ownership — knowing that you are directly responsible for an outcome," and "Impact." Its leadership principles are Dive deep, Take ownership, Bias for action and Do the right thing. Listings promise "small, dynamic teams = massive impact" and "open communication with management and company leadership."

Work-Life Balance

Hopper uses the word itself, so it can be reported as written: nearly every posting lists "Unlimited PTO," and the careers page heads the same perk "Unlimited time off" before adding, "We're a travel company and we actually mean it. Enjoy that vacation time!" Parental leave is described but not quantified: "Please ask us about our very generous parental leave, much above industry standards." The rest of the picture is remote-first infrastructure — a work-from-home stipend, FlexDesk co-working on demand, and a yearly travel credit to spend on the time off you take.

Perks and Benefits

  • "Unlimited PTO," in Hopper's own wording on nearly every posting
  • 100% employer-paid medical, dental and vision cover in the US and Canada
  • Pre-IPO equity packages
  • 100% remote roles, hired across four continents
  • FlexDesk co-working access on demand
  • Work-from-home stipend
  • Carrot Cash travel stipend: $200 a year to spend in the app
  • 401(k), Canadian RRSP or UK Smart Pension, depending on country
  • Parental leave Hopper describes as "much above industry standards"

Open Positions

39 jobs