Updated June 1, 2026

20 open positions

Penetration Testing Jobs with a Great Work-Life Balance

Browse 20+ penetration testing jobs at companies offering unlimited PTO and generous_parental_leave—full pay and a better work-life balance. 9 new this week.

Hiring companies include MongoDB, CHAOS Industries, and Automattic. Schedules on offer include unlimited PTO, generous_parental_leave, and flexible hours.

Jobs

New This Week

10+

Companies

Updated Daily

Trusted by 350+ companies offering reduced work schedules

20 Jobs Found

AI Security Specialist

Deel

RemoteEurope +3 more

5 day weekUnlimited PTO

Senior Security Research Engineer

20d

Automattic

RemoteWorldwide

5 day weekVery Flexible$70k - $170k

Advanced Security Engineer

1mo

Feedzai

RemotePortugal

4 day week during Summer

Senior Application Security Engineer

1mo

Temporal

RemoteUSA

5 day weekUnlimited PTO$180k - $225k

Senior Web Security Engineer, Browser Platform

1mo

DuckDuckGo

RemoteWorldwide

5 day weekVery Flexible$179k

Staff Security Engineer

22d

Assured

RemoteUSA

5 day weekUnlimited PTO

Senior Engineer, Offensive Security

1mo

Twilio

RemoteIndia

5 day weekUnlimited PTO

Lead Product Security Engineer

1mo

Dremio

RemoteUSA

5 day weekUnlimited PTO

Cybersecurity Assessment Specialist

Boeing

OnsiteBoulder, USA

9 day fortnight

Cybersecurity Incident Response Specialist

Geotab

HybridAtlanta, USA

5 day weekVery Flexible

Senior Product Security Engineer, Server

MongoDB

HybridDublin, Ireland

5 day weekGenerous parental leave

Senior Product Security Engineer, Server

MongoDB

HybridDublin, Ireland

5 day weekGenerous parental leave

Senior Product Security Engineer, Server

MongoDB

HybridCork, Ireland

5 day weekGenerous parental leave

Cybersecurity Requirement Verifications & Controls Specialist

1mo

Intesa Sanpaolo

HybridNapoli, Italy

4 day week100% pay

Software Engineer, Cybersecurity Products

Anthropic

HybridSan Francisco +3 more

5 day weekGenerous parental leave$320k - $405k

Cybersecurity Engineer, Product Security

CHAOS Industries

OnsiteSan Francisco, USA

5 day weekUnlimited PTO

Cybersecurity Engineer, Product Security

CHAOS Industries

OnsiteWashington, USA

5 day weekUnlimited PTO

Application Security Engineer

Polymarket

OnsiteNew York, USA

5 day weekUnlimited PTO

Senior Offensive Security Manager

1mo

Postman

HybridSan Francisco, USA

5 day weekUnlimited PTO$250k - $300k

Staff Offensive Security Engineer

22d

Greenlight

HybridBengaluru, India

5 day weekUnlimited PTO

How we curate this list

We track companies that publicly offer reduced-hours schedules — 4-day weeks, 9-day fortnights, half-day Fridays, and more. This page refreshes daily; companies that drop the policy are removed. Read about our editorial standards →

Last reviewed: June 1, 2026

Got questions?

Frequently asked questions

Everything you need to know about 4-day week jobs

Employers hiring for Penetration Testing on this page include MongoDB, CHAOS Industries, and Automattic. Penetration Testing 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 Penetration Testing is a primary requirement or one of several preferred skills — expand any role above to see the full stack and responsibilities.

Penetration Testing roles span the full seniority range — we list 20 open roles requiring Penetration Testing 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 — Penetration Testing 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.

Yes — companies listed on 4dayweek.io commit to full salary parity regardless of schedule. Penetration Testing roles in tech and data typically command premium rates at both reduced-hours and traditional employers. Specific ranges depend on seniority, location, and the specific 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 Penetration Testing 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 Penetration Testing on current listings.