40 open positions

Challenger Jobs with a Great Work-Life Balance

Browse 40+ challenger jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 6 new this week. Hiring companies include Okta, Contentsquare, and Osano.

Schedules on this page

half-day Fridays 2
generous PTO 1
flexible hours 2
unlimited PTO 14
best places to work 21

Updated October 3, 2026

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Area Sales Director, Enterprise (Auth0)

Okta · Remote · Florida +3 more

57 · GoodBest Place to Work

SaaS Sales Manager

Osano · Remote · USA

61 · GoodUnlimited PTO

SaaS Sales Manager

Osano · Remote · USA

61 · GoodUnlimited PTO

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Sales Manager

23d

Osano · Remote · Austin, TX, USA

61 · GoodUnlimited PTO

Sales Enablement Lead

4mo

Geotab · Remote · Oakville, ON, Canada

61 · GoodFlexible Hours

Account Executive (Korean Speaking)

2mo

Deepgram · Remote · Singapore, Singapore

60 · GoodUnlimited PTO

Account Executive (Singapore)

2mo

Deepgram · Remote · Singapore, Singapore

60 · GoodUnlimited PTO

Strategic Account Executive

15d

Checkr · Remote · USA

59 · GoodUnlimited PTO$230k – $351k

Strategic Account Executive

4mo

Collectly · Remote · USA

59 · GoodUnlimited PTO

Strategic Account Executive, Mining

15d

Armada · Remote · Australia

58 · GoodUnlimited PTO

Regional Sales Manager, Enterprise

17d

Okta · Remote · San Francisco, CA, USA

57 · GoodBest Place to Work

Regional Sales Manager, Enterprise

1mo

Okta · Remote · Los Angeles, CA or San Francisco, CA

57 · GoodBest Place to Work

Director of Sales (LATAM)

2mo

Mesh · Remote · North America or South America

57 · GoodUnlimited PTO

Large Enterprise Account Executive Auth0

2mo

Okta · Remote · Germany

57 · GoodBest Place to Work

Strategic Account Executive

2mo

Okta · Remote · Germany

57 · GoodBest Place to Work

Enterprise Account Executive

3mo

Okta · Remote · Tennessee, USA

57 · GoodBest Place to Work

Sales Development Rep (SaaS)

Infinity · Hybrid · Manchester, UK

70 · GreatHalf Day Fridays£35k

Enterprise Account Executive

Contentsquare · Hybrid · Sydney, Australia

58 · GoodBest Place to Work

Account Executive / Account Manager, MM (India)

Apollo.io · Hybrid · Bangalore, India

59 · GoodBest Place to Work

Manager, GTM Enablement

11d

Basis · Onsite · New York, NY, USA

56 · GoodUnlimited PTO$150k – $250k

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Frequently asked questions

Everything you need to know about 4-day week jobs

Employers hiring for Challenger on this page include Okta, Contentsquare, and Osano. Challenger 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 Challenger is a primary requirement or one of several preferred skills — expand any role above to see the full stack and responsibilities.

Challenger roles span the full seniority range — we list 40 open roles requiring Challenger 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 — Challenger 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. Challenger 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 Challenger 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 Challenger on current listings.

Browse all 40 jobs

Challenger Jobs with a Great Work-Life Balance

Browse 40+ challenger jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 6 new this week. Hiring companies include Okta, Contentsquare, and Osano.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

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