67 open positions

Challenger Sales Jobs with a Great Work-Life Balance

Browse 67+ challenger sales jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 3 new this week. Hiring companies include MongoDB, Orb, and Okta.

Schedules on this page

summer Fridays 1
flexible hours 1
unlimited PTO 9
best places to work 8
generous parental leave 48

Updated August 26, 2026

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Account Executive

NEW

16h

Guidewire · Remote · USA

58 · GoodBest Place to Work$120kPro · early access

Lead Account Executive, Commercial

25d

HackerOne · Remote · USA

62 · GoodUnlimited PTO$110k – $135k

Lead Account Executive, Commercial, Central

25d

HackerOne · Remote · Chicago, USA

62 · GoodUnlimited PTO$110k – $143k

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Account Executive - Enterprise

1mo

CaptivateIQ · Remote · USA

62 · GoodFlexible Hours$300k

Strategic Account Executive

2mo

HopSkipDrive · Remote · USA

60 · GoodSummer Fridays$95k

Senior Account Executive - Enterprise Sales (Japan)

2mo

New Relic · Remote · Japan

59 · GoodBest Place to Work

Senior Account Executive - Enterprise Sales (Japan)

2mo

New Relic · Remote · Japan

59 · GoodBest Place to Work

Senior Account Executive - Enterprise Sales (Japan)

2mo

New Relic · Remote · Japan

59 · GoodBest Place to Work

Account Executive (Enterprise) - West Region

2mo

Iterable · Remote · USA

58 · GoodBest Place to Work$267k – $311k

Director of Sales (LATAM)

23d

Mesh · Remote · Mexico

57 · GoodUnlimited PTO

Enterprise Account Executive

2mo

Okta · Remote · São Paulo, Brazil

57 · GoodBest Place to Work

Enterprise Account Executive

2mo

Okta · Remote · Alabama or Mississippi

57 · GoodBest Place to Work

Enterprise Account Executive, Growth

2mo

MongoDB · Remote · Chicago, USA

57 · GoodGenerous Parental Leave$150k

Enterprise Account Executive, Growth

2mo

MongoDB · Remote · Michigan or Ohio

57 · GoodGenerous Parental Leave$150k

Account Executive - Enterprise Sales

2mo

New Relic · Remote · Japan

59 · GoodBest Place to Work

Account Executive - X3

NEW

Sage · Hybrid · Newcastle, UK

62 · GoodGenerous PTO

Principal Partner Specialist

MongoDB · Hybrid · Beijing, China

57 · GoodGenerous Parental Leave

Strategic Sales Manager

22d

EliseAI · Onsite · Austin, TX, USA

59 · GoodUnlimited PTO$200k

Strategic Sales Manager | Housing

3mo

EliseAI · Onsite · New York City, NY, USA

59 · GoodUnlimited PTO

Enterprise Account Executive

1mo

Okta · Hybrid · London, UK

57 · GoodBest Place to Work£164k – £226k

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Frequently asked questions

Everything you need to know about 4-day week jobs

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

Challenger Sales roles span the full seniority range — we list 67 open roles requiring Challenger Sales 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 Sales 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 Sales 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 Sales 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 Sales on current listings.

Browse all 67 jobs

Challenger Sales Jobs with a Great Work-Life Balance

Browse 67+ challenger sales jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 3 new this week. Hiring companies include MongoDB, Orb, and Okta.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

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