42 open positions

Penetration Testing Jobs with a Great Work-Life Balance

Browse 42+ penetration testing jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 4 new this week. Hiring companies include ServiceNow, Anthropic, and MongoDB.

Schedules on this page

4-day weeks 2
flexible hours 2
unlimited PTO 8
best places to work 17
generous parental leave 9

Updated August 21, 2026

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New this week: 33
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Senior Security Researcher (Red Team)

NEW

19h

Pindrop · Remote · USA

63 · GoodUnlimited PTO$125k – $165kPro · early access

Senior Application Security Engineer

1mo

Monarch Money · Remote · USA or Canada

68 · GoodRotating 4 Day Week$180k – $215k

Senior Offensive Security Engineer

17d

Array · Remote · USA or Canada

64 · GoodSummer Fridays$170k

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Senior Application Security Engineer

14d

Clover Health · Remote · USA

63 · GoodUnlimited PTO$169k – $220k

AI Security - Principal Security Research Engineer I

22d

Elastic · Remote · USA

62 · GoodBest Place to Work

Software Engineer, Security

2mo

Render · Remote · USA or Canada

62 · GoodBest Place to Work$170k – $290k

Staff Engineer - Offensive Security

1mo

Twilio · Remote · USA

61 · GoodUnlimited PTO$156k – $229k

Senior Web Security Engineer, Browser Platform

4mo

DuckDuckGo · Remote · USA

61 · GoodFlexible Hours$179k

Staff Security Engineer

3mo

Assured · Remote · USA

60 · GoodUnlimited PTO$220k – $240k

Senior Application Security Engineer

2mo

Apollo.io · Remote · Canada or USA

59 · GoodBest Place to Work

Senior Cloud Security Engineer

15d

Iterable · Remote · USA

58 · GoodBest Place to Work$141k – $221k

Staff Product Security Engineer

1mo

Greenlight · Remote · USA

58 · GoodUnlimited PTO$165k – $200k

Manager, Offensive Security

1mo

Gainsight · Remote · Texas +4 more

57 · GoodBest Place to Work$160k – $200k

Frontier AI Security Threat Hunter

1mo

Wealthsimple · Remote · Canada

57 · GoodGenerous Parental Leave$151k – $189k

Lead Penetration Test Engineer

NEW

S&P Global · Hybrid · Princeton, NJ +8 more

56 · GoodGenerous Parental Leave$135k – $200kPro · early access

Cybersecurity Engineer

Workday UK and Ireland · Hybrid · Dublin, Ireland

68 · GoodGenerous PTO€70k – €105k

Penetration Tester

1mo

Intesa Sanpaolo · Hybrid · Napoli, Italy

83 · Great4 Day Work Week€45k

Penetration Tester

4mo

Intesa Sanpaolo · Hybrid · Napoli, Italy

83 · Great4 Day Work Week€50k

Associate Director, Principal Security

S&P Global · Hybrid · Gurugram, India

56 · GoodGenerous Parental Leave

Principal Cyber Security Analyst

17d

Scottish Government · Hybrid · Glasgow, UK

71 · GreatCompressed Work Week

Showing 20 of 42

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Frequently asked questions

Everything you need to know about 4-day week jobs

Employers hiring for Penetration Testing on this page include ServiceNow, Anthropic, and MongoDB. 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 42 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.

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. 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 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.

Penetration Testing Jobs with a Great Work-Life Balance

Browse 42+ penetration testing jobs at companies offering unlimited PTO and best places to work—for a better work-life balance. 4 new this week. Hiring companies include ServiceNow, Anthropic, and MongoDB.

Job listings

Frequently asked questions

Job listings

Frequently asked questions

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