37 open positions

Challenger Jobs with a Great Work-Life Balance

Browse 37+ challenger jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 2 new this week. Hiring companies include Okta, Mesh, and Contentsquare.

Schedules on this page

flexible hours 1
unlimited PTO 11
best places to work 25

Updated August 24, 2026

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2
New this week: 15
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Enablement Specialist, Sales Execution

Five9 · Remote · USA

57 · GoodBest Place to Work$65k – $181k

Regional Sales Manager, Enterprise

Okta · Remote · San Francisco, CA, USA

57 · GoodBest Place to Work

Sales Enablement Lead

2mo

Geotab · Remote · Oakville, ON, Canada

61 · GoodFlexible Hours

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GTM Enablement Leader (EMEA)

1mo

New Relic · Remote · Ireland

59 · GoodBest Place to Work

Strategic Account Executive

3mo

Collectly · Remote · USA

59 · GoodUnlimited PTO

Large Enterprise Account Executive Auth0

20d

Okta · Remote · Germany

57 · GoodBest Place to Work

Director of Sales

21d

Mesh · Remote · Europe

57 · GoodUnlimited PTO

Enterprise Account Executive

2mo

Okta · Remote · Tennessee, USA

57 · GoodBest Place to Work

Area Sales Director, Strategic

2mo

Okta · Remote · New York, NY, USA

57 · GoodBest Place to Work$376k – $517k

Strategic Account Executive, Auth0

2mo

Okta · Remote · San Francisco, CA, USA

57 · GoodBest Place to Work

Regional Sales Manager, Enterprise

2mo

Okta · Remote · Boston, MA +2 more

57 · GoodBest Place to Work$288k – $360k

Regional Sales Manager, Enterprise

2mo

Okta · Remote · Chicago, IL, USA

57 · GoodBest Place to Work$288k – $396k

Enterprise Account Executive, Auth0

2mo

Okta · Remote · Vancouver, BC, Canada

57 · GoodBest Place to Work

Enterprise Account Executive, UKI

11d

Contentsquare · Hybrid · London, UK

58 · GoodBest Place to Work

Revenue Enablement Manager

12d

Postman · Onsite · Singapore, Singapore

59 · GoodUnlimited PTO

Account Executive

25d

Lightning AI · Hybrid · New York, NY or San Francisco, CA

60 · GoodUnlimited PTO$150k

GTM Enablement Program Manager

3mo

EliseAI · Onsite · New York City, NY or Boston, MA

59 · GoodUnlimited PTO$150k – $190k

Director of Enterprise Sales

3mo

Collectly · Hybrid · San Francisco, CA, USA

59 · GoodUnlimited PTO$330k – $390k

Mid-market Account Executive

1mo

Contentsquare · Hybrid · Dubai, United Arab Emirates

58 · GoodBest Place to Work

Director of Sales, Commercial (Europe)

2mo

Klaviyo · Hybrid · Dublin, Ireland

58 · GoodUnlimited PTO€144k – €216k

Showing 20 of 37

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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, Mesh, and Contentsquare. 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 37 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.

Challenger Jobs with a Great Work-Life Balance

Browse 37+ challenger jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 2 new this week. Hiring companies include Okta, Mesh, and Contentsquare.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

Narrow these jobs