28 open positions

AI Fluency Jobs with a Great Work-Life Balance

Browse 28+ ai fluency jobs at companies offering generous PTO and unlimited PTO—for a better work-life balance. 2 new this week. Hiring companies include Kit, Dropbox, and Guidewire.

Schedules on this page

rotating 4-day weeks 2
generous PTO 4
unlimited PTO 11
best places to work 10
generous parental leave 1

Updated October 14, 2026

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New this week: 21
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Program Owner, EMEA Field & Cross-Persona Enablement

Guidewire · Remote · Ireland +3 more

58 · GoodBest Place to Work

Senior Customer Success Manager

CoderPad · Remote · USA

62 · GoodUnlimited PTO$120k – $130k

Client Strategy Manager, Activation

InMarket · Remote · USA

61 · GoodUnlimited PTO$90k – $100k

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Principal, Procurement

28d

Monarch Money · Remote · USA

68 · GoodRotating 4 Day Week$175k – $205k

Principal, Strategic Operations

2mo

Monarch Money · Remote · USA

68 · GoodRotating 4 Day Week$170k – $205k

Strategic Account Executive

15d

CoderPad · Remote · USA

62 · GoodUnlimited PTO$145k – $165k

Senior Product Manager - Email & Publishing Tools

17d

Kit · Remote · USA

62 · GoodGenerous PTO$173k

Senior Product Manager - Content Creation

17d

Kit · Remote · USA

62 · GoodGenerous PTO$173k

Senior Product Manager

17d

Kit · Remote · USA

62 · GoodGenerous PTO$173k

Product Manager

20d

Dropbox · Remote · Canada

62 · GoodBest Place to Work

Product Manager

20d

Dropbox · Remote · Mexico

62 · GoodBest Place to Work

Director of People Operations

29d

Chainguard · Remote · USA

62 · GoodBest Place to Work$204k – $240k

Enterprise/Sr. Enterprise Account Executive

3mo

Runway · Remote · USA

62 · GoodUnlimited PTO$300k – $375k

Group Product Marketing Manager

14d

Affirm · Remote · USA

61 · GoodBest Place to Work$195k – $280k

Payment Operations Analyst

25d

Gusto · Remote · Seattle, WA, USA

61 · GoodUnlimited PTO$97k – $121k

Staff Product Manager (Product-Led Growth)

2mo

Deepgram · Remote · USA

60 · GoodUnlimited PTO$200k – $268k

Senior Employee Relations Partner (French Speaking)

21d

Guidewire · Remote · Ireland +2 more

58 · GoodBest Place to Work

Senior Product Manager - Publishing

17d

Kit · Remote · USA

62 · GoodGenerous PTO$173k

Brand Designer

Ascend · Onsite · San Francisco, CA, USA

57 · GoodUnlimited PTO

Manager, SMB Account Management, Food and Beverage

4mo

Block · Hybrid · Chicago, IL, USA

61 · GoodUnlimited PTO$158k – $238k

Showing 20 of 28

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Frequently asked questions

Everything you need to know about 4-day week jobs

Employers hiring for Ai Fluency on this page include Kit, Dropbox, and Guidewire. Ai Fluency 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 Ai Fluency is a primary requirement or one of several preferred skills — expand any role above to see the full stack and responsibilities.

Ai Fluency 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 — Ai Fluency 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. Ai Fluency 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 Ai Fluency 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 Ai Fluency on current listings.

AI Fluency Jobs with a Great Work-Life Balance

Browse 28+ ai fluency jobs at companies offering generous PTO and unlimited PTO—for a better work-life balance. 2 new this week. Hiring companies include Kit, Dropbox, and Guidewire.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

Narrow these jobs