17 open positions

Challenger Jobs with a Great Work-Life Balance

Browse 17+ challenger jobs at companies offering half-day Fridays and unlimited PTO—for a better work-life balance. Hiring companies include Contentsquare, Osano, and Checkr.

Schedules on this page

half-day Fridays 2
unlimited PTO 6
best places to work 9

Updated October 23, 2026

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11
Companies

Senior Sales Executive - Oceania

20d

Revinate · Remote · Australia or New Zealand

74 · GreatHalf Day Fridays

SaaS Sales Manager

28d

Osano · Remote · USA

61 · GoodUnlimited PTO

SaaS Sales Manager

28d

Osano · Remote · USA

61 · GoodUnlimited PTO

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Sales Manager

1mo

Osano · Remote · Austin, TX, USA

61 · GoodUnlimited PTO

Account Executive (Korean Speaking)

3mo

Deepgram · Remote · Singapore, Singapore

60 · GoodUnlimited PTO

Strategic Account Executive

1mo

Checkr · Remote · USA

59 · GoodUnlimited PTO$299k – $351k

Account Executive / Account Manager, MM

Apollo.io · Hybrid · Bangalore, India

59 · GoodBest Place to Work

Strategic Account Executive - India & SEA

Contentsquare · Hybrid · Singapore, Singapore

58 · GoodBest Place to Work

Sales Development Rep (SaaS)

26d

Infinity · Hybrid · Manchester, UK

70 · GreatHalf Day Fridays£35k

Director of Enterprise Sales

5mo

Collectly · Hybrid · San Francisco, CA, USA

59 · GoodUnlimited PTO$330k – $390k

Enterprise Account Executive

24d

Contentsquare · Hybrid · Sydney, New South Wales, Australia

58 · GoodBest Place to Work

Enterprise Account Executive, UKI

2mo

Contentsquare · Hybrid · London, UK

58 · GoodBest Place to Work

Senior Sales Manager Banking

21d

Experian · Hybrid · Düsseldorf, Germany

57 · GoodBest Place to Work

Sales Director, Latam

1mo

Braze · Hybrid · São Paulo, Brazil

57 · GoodBest Place to Work

Account Executive Auth0

3mo

Okta · Hybrid · Madrid, Spain

57 · GoodBest Place to Work

Strategic Enterprise Account Executive

3mo

Contentsquare · Hybrid · London, UK

58 · GoodBest Place to Work

Enterprise Account Executive - KSA

4mo

Contentsquare · Hybrid · Riyadh, Saudi Arabia

58 · GoodBest Place to Work

Showing 17 of 17

Got questions?

Frequently asked questions

Everything you need to know about 4-day week jobs

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

Challenger 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 — Challenger 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. Challenger 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 Challenger 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 Challenger on current listings.