48 open positions

Entrepreneurial Jobs with a Great Work-Life Balance

Browse 48+ entrepreneurial jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 5 new this week. Hiring companies include Process Street, Toast, and Ledgebrook.

Schedules on this page

4-day weeks 1
flexible hours 3
unlimited PTO 28
best places to work 13
generous parental leave 2

Updated October 3, 2026

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Cyber Underwriter (West Coast)

NEW

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$75k – $135k

Cyber Underwriter (West Coast)

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$75k – $135k

Strategic Account Executive

Twilio · Remote · USA

61 · GoodUnlimited PTO$147k – $184k

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Cyber Underwriter (West Coast)

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$75k – $135k

Staff Product Manager (USA/Europe)

2mo

Hospitable · Remote · Oregon, USA

73 · GreatGenerous PTO$174k – $214k

Principal Wealth Advisor

Savvy Wealth · Remote · USA

57 · GoodUnlimited PTO$200k – $1M

Account Executive

10d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Account Executive

10d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Account Executive

10d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Senior Product Manager, Ad Monetization

16d

RevenueCat · Remote · Japan or UK

65 · GoodFlexible Hours$230k

Product Manager, Community Support

18d

Airbnb · Remote · San Francisco, CA, USA

64 · GoodFlexible Hours$200k – $240k

Market Manager - Vacation Rental

3mo

Airbnb · Remote · Tokyo, Japan

64 · GoodFlexible Hours

Strategic Partnerships Manager - AI/API

2mo

Mercury · Remote · USA

62 · GoodUnlimited PTO$163k – $226k

Financial Wealth Advisor (Focus Team)

2mo

Farther · Remote · USA

59 · GoodUnlimited PTO

Strategic Cuisines - Korean AE (Central)

1mo

Toast · Remote · Huntsville, AL, USA

58 · GoodBest Place to Work

Strategic Cuisines Flex Account Executive, Mandarin

1mo

Toast · Remote · Huntsville, AL, USA

58 · GoodBest Place to Work

Bilingual Strategic Cuisines Account Executive (Spanish)

3mo

Toast · Remote · Huntsville, AL, USA

58 · GoodBest Place to Work$115k – $185k

Solution Consultant (Pre-sales)

29d

Nexthink · Remote · Munich, Germany

57 · GoodUnlimited PTO

Staff Product Manager - Occupational Health (New Ventures)

2mo

Wellhub · Remote · Brazil

57 · GoodBest Place to Work

Account Executive

10d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Showing 20 of 48

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Frequently asked questions

Everything you need to know about 4-day week jobs

Employers hiring for Entrepreneurial on this page include Process Street, Toast, and Ledgebrook. Entrepreneurial roles appear most frequently in engineering, data, and platform teams at companies that have adopted a reduced-hours schedule. Each listing indicates the seniority level and whether Entrepreneurial is a primary requirement or one of several preferred skills — expand any role above to see the full stack and responsibilities.

Entrepreneurial roles span the full seniority range — we list 48 open roles requiring Entrepreneurial across entry-level, mid-level, senior, lead, and staff/principal positions. Senior and above tend to dominate because employers offering reduced-hours schedules often lean toward experienced individual contributors who can deliver consistently in fewer hours. Filter by level in the sidebar to narrow the list above.

Lead with measurable outcomes over time spent — Entrepreneurial hiring managers at reduced-hours companies care about delivered value, not hours worked. Highlight projects where you shipped at a steady cadence, collaborated asynchronously, or reduced engineering toil through automation or tooling. Include concrete metrics (latency improvements, adoption numbers, cost reductions) rather than vague duty descriptions. Expand listings above to see the exact framing each employer uses in their job descriptions.

For the full-pay schedules here — 4-day weeks and 9-day fortnights — yes: you keep a full-time salary for a shorter week. Part-time and pro-rata roles instead scale pay to hours, and each listing makes the arrangement clear. Entrepreneurial roles in tech and data typically command premium rates at both reduced-hours and traditional employers; specific ranges depend on seniority, location, and sub-specialty (e.g. backend vs frontend, infra vs ML). Individual listings above show exact bands where the employer publishes them.

Depends on the role, but Entrepreneurial candidates who also demonstrate async communication, clean documentation, and cross-functional collaboration are typically strong fits for reduced-hours employers — those companies rely on written-first communication and high-context handoffs to operate on a compressed schedule. Technical-adjacent skills vary by stack. Browse the top skills shown in the sidebar to see which tags co-occur most often with Entrepreneurial on current listings.

Entrepreneurial Jobs with a Great Work-Life Balance

Browse 48+ entrepreneurial jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 5 new this week. Hiring companies include Process Street, Toast, and Ledgebrook.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

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