58 open positions

Entrepreneurial Jobs with a Great Work-Life Balance

Browse 58+ entrepreneurial jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 13 new this week. Hiring companies include Process Street, Toast, and Airbnb.

Schedules on this page

summer Fridays 1
flexible hours 5
unlimited PTO 32
best places to work 16
generous parental leave 2

Updated October 10, 2026

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New this week: 25
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Product Sales Specialist (EMEA)

NEW

Cribl · Remote · UK

62 · GoodUnlimited PTO

Senior Product Manager

NEW

Geotab · Remote · USA

61 · GoodFlexible Hours

Staff Product Manager (USA/Europe)

2mo

Hospitable · Remote · Oregon, USA

73 · GreatGenerous PTO$174k – $214k

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Strategic Account Executive

10d

Twilio · Remote · USA

61 · GoodUnlimited PTO$147k – $184k

Senior Product Manager, Ad Monetization

23d

RevenueCat · Remote · Japan or UK

65 · GoodFlexible Hours$230k

Product Manager, Community Support

25d

Airbnb · Remote · USA

64 · GoodFlexible Hours$200k – $240k

Market Manager - Vacation Rental

3mo

Airbnb · Remote · Tokyo, Japan

64 · GoodFlexible Hours

Account Executive

17d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Account Executive

17d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Account Executive

17d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Professional Liability Territory & Healthcare Lead (West)

1mo

Ledgebrook · Remote · USA

62 · GoodUnlimited PTO$140k – $170k

Principal Product Manager, Lighthouse

3mo

Owner.com · Remote · USA or Canada

62 · GoodUnlimited PTO$275k – $300k

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

2mo

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

Principal Wealth Advisor

14d

Savvy Wealth · Remote · USA

57 · GoodUnlimited PTO$200k – $1M

Staff Product Manager - Occupational Health (New Ventures)

2mo

Wellhub · Remote · Brazil

57 · GoodBest Place to Work

Account Executive

17d

Process Street · Remote · USA

63 · GoodUnlimited PTO

Account Executive

17d

Process Street · Remote · USA

63 · GoodUnlimited PTO

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Got questions?

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 Airbnb. Entrepreneurial roles appear most frequently in engineering, data, and platform teams at companies that offer a 4-day week or another flexible 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 on this page span seniority levels, from entry-level and mid-level through senior, lead, and staff or principal positions. Filter by level in the sidebar to narrow the list above to the ones that fit you.

Lead with measurable outcomes over time spent — Entrepreneurial hiring managers at companies that run 4-day weeks or flexible schedules 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.

Pay depends on the role, seniority, location, and employer — not on the schedule alone. Entrepreneurial roles in tech and data typically command premium rates, and specific ranges depend on seniority 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 employers that run 4-day weeks or flexible schedules — those teams rely on written-first communication and high-context handoffs. 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.

Browse all 58 jobs

Entrepreneurial Jobs with a Great Work-Life Balance

Browse 58+ entrepreneurial jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 13 new this week. Hiring companies include Process Street, Toast, and Airbnb.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

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