29 open positions

Entrepreneurial Jobs with a Great Work-Life Balance

Browse 29+ entrepreneurial jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 3 new this week. Hiring companies include Toast, Nexthink, and Khan Academy.

Schedules on this page

summer Fridays 2
generous PTO 1
unlimited PTO 9
best places to work 15
generous parental leave 2

Updated August 23, 2026

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Strategic Cuisines Account Executive - Spanish

NEW

Toast · Remote · Huntsville, AL, USA

58 · GoodBest Place to Work

Staff Product Manager (USA/Europe)

26d

Hospitable · Remote · Oregon, USA

73 · GreatGenerous PTO$174k – $214k

Strategic Partnerships Manager - AI/API

1mo

Mercury · Remote · USA

62 · GoodUnlimited PTO$163k – $226k

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Principal Product Manager, Lighthouse

1mo

Owner.com · Remote · USA or Canada

62 · GoodUnlimited PTO$275k – $300k

Senior Product Manager, Studio Team

13d

GameChanger · Remote · USA

59 · GoodUnlimited PTO$160k – $180k

Principal Product Manager, Enterprise Commerce Platform

1mo

Twilio · Remote · USA

61 · GoodUnlimited PTO$171k – $252k

Financial Wealth Advisor (Focus Team)

20d

Farther · Remote · USA

59 · GoodUnlimited PTO

Bilingual Strategic Cuisines Flex Account Executive

18d

Toast · Remote · Huntsville, AL, USA

58 · GoodBest Place to Work

Strategic Cuisines Account Executive - Bilingual Spanish

23d

Toast · Remote · Huntsville, AL, USA

58 · GoodBest Place to Work

Solution Consultant (Pre-sales)

24d

Nexthink · Remote · Munich, Germany

57 · GoodUnlimited PTO

Staff Product Manager - Occupational Health (New Ventures)

1mo

Wellhub · Remote · Brazil

57 · GoodBest Place to Work

Bilingual Strategic Cuisines Account Executive (Spanish)

1mo

Toast · Remote · Huntsville, AL, USA

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

Strategic Cuisines Thai & Asian Cuisine District Manager

1mo

Toast · Remote · USA

58 · GoodBest Place to Work

Bilingual Strategic Cuisines Account Executive (Spanish)

1mo

Toast · Remote · Huntsville, AL, USA

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

Senior Product Manager, Toast Now

2mo

Toast · Remote · USA

58 · GoodBest Place to Work$125k – $254k

Measurement Partner II

Pinterest · Hybrid · Paris, France

60 · GoodUnlimited PTO€49k – €91k

Sales Development Representative

Garage · Onsite · New York City, NY, USA

57 · GoodUnlimited PTO$85k – $115k

Training Lead - Physics

18d

Khan Academy · Hybrid · Vijayawada, Andhra Pradesh, India

63 · GoodSummer Fridays

Training Lead - Biology

18d

Khan Academy · Hybrid · Vijayawada, Andhra Pradesh, India

63 · GoodSummer Fridays

Solution Consultant

1mo

Nexthink · Hybrid · Madrid, Spain

57 · GoodUnlimited PTO€60k – €78k

Showing 20 of 29

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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 Toast, Nexthink, and Khan Academy. 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 29 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 29+ entrepreneurial jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 3 new this week. Hiring companies include Toast, Nexthink, and Khan Academy.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

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