13 Remote Companies Offering Sabbaticals

85

Remote Score

Webflow

Remote-First

IT Services & Consulting

800 employees58 open positions

Webflow has been building toward a remote-first vision since 2012, now with 800 employees across the globe. Sabbatical arrives at five years. At that scale, a company that still maintains a genuine remote-first culture—and backs it with a long-tenure benefit—stands out.

86

Remote Score

Mercury

Remote-First

Financial Services

52 open positions

Mercury puts every financial workflow for ambitious companies in one place—and invests in the people building it. Six weeks of paid sabbatical after five years signals this isn't a churn-and-burn fintech. It's a company thinking in longer time horizons than most.

81

Remote Score

Instacart

Remote-First

169 open positions

Instacart went Flex First in 2022—and over 70% of their corporate team is now fully remote-eligible. Four weeks of sabbatical around the four-year mark is an early perk by big-company standards. A 2022 policy shift that actually changed how people work, not just where.

96

Remote Score

Kit

Fully Remote

Software Development

100 employees10 open positions

Kit has run a fully distributed team of 170 for over a decade—long before remote became a hiring trend. After five years, employees earn four weeks of paid sabbatical. That's a creator-economy company that invests in its own people the way it helps creators invest in theirs.

93

Remote Score

Buffer

Fully Remote

Social Media Management

MarTechSaaS Platform

50 employees6 open positions

Buffer was remote before remote was cool. Their six-week paid sabbatical every five years comes with a team spanning 30+ countries and a publicly documented salary formula. Transparency isn't just a value—it's how they operate.

71

Remote Score

Kong Inc.

Structured Hybrid

Software Development

850 employees107 open positions

Kong runs the API infrastructure that powers microservices at scale for enterprises worldwide. Four weeks of paid sabbatical every five years is a concrete signal in an industry that often talks culture but skimps on rest. Remote-first, infrastructure-serious.

96

Remote Score

Close

Fully Remote

Software Development

100 employees7 open positions

Close has been remote since 2013—before most companies had a remote policy at all. Bootstrapped and profitable with 110 employees, they offer four weeks of fully paid sabbatical every five years. Longevity is rewarded, not just tolerated.

87

Remote Score

CareMessage

Fully Remote

Healthcare & Life Sciences

HealthTech

48 employees9 open positions

Founded by Stanford students in 2012, CareMessage now reaches 7M+ patients with health messaging for underserved communities. At four years, employees earn 20 days of fully paid sabbatical. A rare combination: nonprofit mission, remote culture, and structured rest built into policy.

80

Remote Score

Acceleration Partners

Fully Remote

Advertising

Marketing Agency

17 open positions

300+ employees across 40+ countries, all in partnership marketing. Acceleration Partners operates at a global scale that demands genuine remote infrastructure—not a perk list. Paid sabbatical after five years rewards the people making that infrastructure work.

90

Remote Score

Help Scout

Fully Remote

Software Development

150 employees0

Help Scout serves 12,000+ companies—including Trello and Mixpanel—with a 140-person team spread across 115+ cities. Sabbatical kicks in at four years, not five. For a distributed team that size, longevity benefits arriving a year earlier is worth noticing.

Prezi

Remote-First

Software Development

200 employees0

Prezi rethought how people present ideas—dynamic, nonlinear, visual. Their 200-person team has sabbatical leave available, though specifics aren't publicly detailed. A company built on seeing the big picture offering structured time to step back fits the mission.

37signals

Fully Remote

Software & Internet

SaaS PlatformDevTools+1 more

100 employees0

37signals has been remote since 1999, wrote the book on it (literally), and offers the strongest sabbatical on this list: six weeks paid every three years. Bootstrapped, profitable, 80 people. They've never needed an RTO mandate because they never left.