Interviews/Security/Penetration Tester

Hire Penetration Testers
who actually find the bug before the attacker does

With EasyEnv we build a fit test for the role. Use it to cut the noise at the top of the funnel, or to go deep on the candidates who matter.

You can even evaluate how this person works with AI. So you hire the engineer who can ship, not the one who looks good in a slide.

Web · network · systemBurp · nmap · metasploitCTF-style boxesOSCP-gradeLive or take-home

Request a Demo Create a Free Account

Real Linux VM

Not a sandbox

systemd, kernel, full toolchain

Browser-based

Zero install for candidates

One link and they are in

Auto-graded

Pass / fail checks per challenge

Plus the full session replay

A pen tester proves the threat model is wrong. The good ones chain three small bugs into something that wakes the CEO. EasyEnv drops the candidate into a workspace with a real, intentionally broken stack and lets them work without the abstraction of a CTF wrapper.

Inside a live interview

What you see when they work.

Real target, real exploit chain, every keystroke recorded.

billing-api

AMS

Billing-api

src

billing.py

auth.py

models.py

tests

test_billing.pyM

test_auth.py

pyproject.toml

README.md

Pybilling.py

from decimal import Decimal

def calculate_total(items: list[dict]) -> Decimal:

# Sum line totals using Decimal for currency precision

total = Decimal("0")

for item in items:

total += Decimal(str(item["price"])) * item["qty"]

return total

candidate@kali:~

alice@dev:~/billing-api$

● mainPython 3.12

Claude · ready

Claude

You

Refactor calculate_total to use Decimal for currency math, and add a test.

Claude

Ask Claude...

Mike

Sam

How it works

Three steps. Zero infra to maintain.

Pick the fit test

Use a ready-made challenge or ask us to build one for your stack. Live, take-home, or both.

Send one link

The candidate clicks. A full Linux workspace boots in their browser. No installs, no VPN, no zoom-share.

Review at 2x

Replay the session, read the auto-graded checks, and decide. Most reviews take under five minutes.

The problem

Why hiring a Penetration Tester is hard.

Cert lists and CV bullets do not show how someone moves through a box.

A great pen tester reads error messages like a novel. The interview has to surface that habit.

Reporting is half the job. Vague write-ups waste engineering hours.

Modern stacks add cloud, supply chain and CI to the surface. Traditional certs lag behind.

The fit test

What we measure for a Penetration Tester.

Every area runs inside a real production-like workspace. The candidate works in a browser, the session records itself.

Web app exploitation

A realistic app with auth, file upload and SSRF risk. They explain before they pop a shell.

Reconnaissance discipline

A target with noise around it. They tell signal from noise without nmap-bombing.

Privilege escalation

A foothold with a tight blast radius. They escalate by reading config, not by guessing.

Cloud and IAM

A leaked AWS key with one over-permissioned role. They map the blast radius cleanly.

Supply chain attack surface

A CI pipeline with a public dependency they could ship as. They prove the path.

AI in the kill chain

Allow AI for payload generation and grade whether they verify shell commands before running.

The stack we put in front of them.

Real tools, pre-installed, accessible from the workspace terminal.

nmapBurp SuiteOWASP ZAPMetasploitsqlmaphydragobusterffufBloodHoundmimikatzPowerSploitImpacketaws-cliScoutSuitePacuCrackMapExec

Sample challenges

What a Penetration Tester interview looks like.

Pick from our library or ask us to build a challenge for your stack. Each one is a real workspace, not a snippet.

Challenge 01

From upload to metadata

Scenario

A file upload that fetches a preview. The candidate has source, network and a sandbox AWS account.

What you learn

Whether they pivot to instance metadata before they admire the first SSRF.

In the workspace

$ ls challenges/

workspace, runbook.md, README.md

candidate has:

· a real Linux box in the browser
· kubectl, docker, terraform, jq, yq
· cluster, repo and cloud creds pre-wired
· auto-checks running in the background

interviewer sees:

· every keystroke + every command
· terminal + screen recording
· auto-graded pass/fail per check

AI in the loop

Score the engineer, and how they work with AI.

AI is fluent in payloads and lousy at restraint. EasyEnv records every prompt so you see whether the candidate reviewed the suggested command for blast radius before pasting it into a real shell.

Allow or block AI per question, not per interview

Full prompt and response history replayed in the review

Score "verifies AI output" as a separate signal

Ready to hire a Penetration Tester who ships?

Set up your first interview in under an hour. We will help you build a fit test for this role on your stack.

Request a Demo Create a Free Account

Role FAQ

Hiring a Penetration Tester, answered.

Yes. Every workspace is sandboxed and you own it for the duration of the interview. No production targets.

Yes. Sandbox AWS, GCP and Azure accounts plus a private CI runner can be pre-wired into the workspace.

No. The workspace runs in their browser. Terminal, editor, ports and dashboards are all served from the EasyEnv workspace, so candidate setup is zero.

Each challenge has automated checks (did the service come back, did the test pass, did the right log message appear) plus a recording your team can replay. Most reviews take under five minutes.

Yes. AI access is a per-interview setting. Block it for fundamentals, then allow it later in the loop to assess AI collaboration separately.

Interviews/Security/Penetration Tester

Hire Penetration Testers
who actually find the bug before the attacker does

With EasyEnv we build a fit test for the role. Use it to cut the noise at the top of the funnel, or to go deep on the candidates who matter.

You can even evaluate how this person works with AI. So you hire the engineer who can ship, not the one who looks good in a slide.

Web · network · systemBurp · nmap · metasploitCTF-style boxesOSCP-gradeLive or take-home

Request a Demo Create a Free Account

Real Linux VM

Not a sandbox

systemd, kernel, full toolchain

Browser-based

Zero install for candidates

One link and they are in

Auto-graded

Pass / fail checks per challenge

Plus the full session replay

Inside a live interview

What you see when they work.

Real target, real exploit chain, every keystroke recorded.

billing-api

AMS

Billing-api

src

billing.py

auth.py

models.py

tests

test_billing.pyM

test_auth.py

pyproject.toml

README.md

Pybilling.py

from decimal import Decimal

def calculate_total(items: list[dict]) -> Decimal:

# Sum line totals using Decimal for currency precision

total = Decimal("0")

for item in items:

total += Decimal(str(item["price"])) * item["qty"]

return total

candidate@kali:~

alice@dev:~/billing-api$

● mainPython 3.12

Claude · ready

Claude

You

Refactor calculate_total to use Decimal for currency math, and add a test.

Claude

Ask Claude...

Mike

Sam

How it works

Three steps. Zero infra to maintain.

Pick the fit test

Use a ready-made challenge or ask us to build one for your stack. Live, take-home, or both.

Send one link

The candidate clicks. A full Linux workspace boots in their browser. No installs, no VPN, no zoom-share.

Review at 2x

Replay the session, read the auto-graded checks, and decide. Most reviews take under five minutes.

The problem

Why hiring a Penetration Tester is hard.

Cert lists and CV bullets do not show how someone moves through a box.

A great pen tester reads error messages like a novel. The interview has to surface that habit.

Reporting is half the job. Vague write-ups waste engineering hours.

Modern stacks add cloud, supply chain and CI to the surface. Traditional certs lag behind.

The fit test

What we measure for a Penetration Tester.

Every area runs inside a real production-like workspace. The candidate works in a browser, the session records itself.

Web app exploitation

A realistic app with auth, file upload and SSRF risk. They explain before they pop a shell.

Reconnaissance discipline

A target with noise around it. They tell signal from noise without nmap-bombing.

Privilege escalation

A foothold with a tight blast radius. They escalate by reading config, not by guessing.

Cloud and IAM

A leaked AWS key with one over-permissioned role. They map the blast radius cleanly.

Supply chain attack surface

A CI pipeline with a public dependency they could ship as. They prove the path.

AI in the kill chain

Allow AI for payload generation and grade whether they verify shell commands before running.

The stack we put in front of them.

Real tools, pre-installed, accessible from the workspace terminal.

nmapBurp SuiteOWASP ZAPMetasploitsqlmaphydragobusterffufBloodHoundmimikatzPowerSploitImpacketaws-cliScoutSuitePacuCrackMapExec

Sample challenges

What a Penetration Tester interview looks like.

Pick from our library or ask us to build a challenge for your stack. Each one is a real workspace, not a snippet.

Challenge 01

From upload to metadata

Scenario

A file upload that fetches a preview. The candidate has source, network and a sandbox AWS account.

What you learn

Whether they pivot to instance metadata before they admire the first SSRF.

In the workspace

$ ls challenges/

workspace, runbook.md, README.md

candidate has:

· a real Linux box in the browser
· kubectl, docker, terraform, jq, yq
· cluster, repo and cloud creds pre-wired
· auto-checks running in the background

interviewer sees:

· every keystroke + every command
· terminal + screen recording
· auto-graded pass/fail per check

AI in the loop

Score the engineer, and how they work with AI.

AI is fluent in payloads and lousy at restraint. EasyEnv records every prompt so you see whether the candidate reviewed the suggested command for blast radius before pasting it into a real shell.

Allow or block AI per question, not per interview

Full prompt and response history replayed in the review

Score "verifies AI output" as a separate signal

Ready to hire a Penetration Tester who ships?

Set up your first interview in under an hour. We will help you build a fit test for this role on your stack.

Request a Demo Create a Free Account

Role FAQ

Hiring a Penetration Tester, answered.

Yes. Every workspace is sandboxed and you own it for the duration of the interview. No production targets.

Yes. Sandbox AWS, GCP and Azure accounts plus a private CI runner can be pre-wired into the workspace.

No. The workspace runs in their browser. Terminal, editor, ports and dashboards are all served from the EasyEnv workspace, so candidate setup is zero.

Each challenge has automated checks (did the service come back, did the test pass, did the right log message appear) plus a recording your team can replay. Most reviews take under five minutes.

Yes. AI access is a per-interview setting. Block it for fundamentals, then allow it later in the loop to assess AI collaboration separately.

How to Hire a Penetration Tester | Real Boxes to Break | EasyEnv | EasyEnv

Hire Penetration Testerswho actually find the bug before the attacker does

What you see when they work.

Three steps. Zero infra to maintain.

Pick the fit test

Send one link

Review at 2x

Why hiring a Penetration Tester is hard.

What we measure for a Penetration Tester.

Web app exploitation

Reconnaissance discipline

Privilege escalation

Cloud and IAM

Supply chain attack surface

AI in the kill chain

The stack we put in front of them.

What a Penetration Tester interview looks like.

From upload to metadata

Score the engineer, and how they work with AI.

Ready to hire a Penetration Tester who ships?

Hiring a Penetration Tester, answered.

Hire Penetration Testerswho actually find the bug before the attacker does

What you see when they work.

Three steps. Zero infra to maintain.

Pick the fit test

Send one link

Review at 2x

Why hiring a Penetration Tester is hard.

What we measure for a Penetration Tester.

Web app exploitation

Reconnaissance discipline

Privilege escalation

Cloud and IAM

Supply chain attack surface

AI in the kill chain

The stack we put in front of them.

What a Penetration Tester interview looks like.

From upload to metadata

Score the engineer, and how they work with AI.

Ready to hire a Penetration Tester who ships?

Hiring a Penetration Tester, answered.

Hire Penetration Testers
who actually find the bug before the attacker does

Hire Penetration Testers
who actually find the bug before the attacker does