Company: Evolve Security
Job Type: Full Time
Location: Remote/Hybrid – Chicago, IL (US)
Job Field: Cybersecurity / Penetration Testing
Application Link: Apply Here

Role Overview

Evolve Security is looking for entry-level Associate Penetration Testers to join their team of offensive security professionals. This role is ideal for aspiring pen testers with a solid IT/security foundation who are eager to learn methodologies, tools, and reporting standards in real-world network and cloud assessments.

Associates will gain hands-on experience performing vulnerability scans, configuration assessments, and supporting infrastructure improvements under the guidance of senior team members.

Key Responsibilities

Assist with network and cloud security assessments under senior supervision

Support vulnerability scanning and configuration assessments

Help identify misconfigurations and security weaknesses

Assist in documenting findings and drafting reports for review

Support IT teams with system administration, basic scripting, and automation tasks

Learn penetration testing methodologies, tools, and reporting standards

Required Skills & Qualifications

Technical Skills:

Understanding of IP addressing, subnetting, gateways, DNS, and DHCP

Basic firewall knowledge, traffic management, and ports/protocols (TCP/UDP)

Familiarity with vulnerability and configuration management

Configuring and troubleshooting VPN clients (IPSec, SSL VPN)

Cloud fundamentals: managing VMs, S3/Azure Blob Storage, IAM concepts, DNS zones

Using cloud-native monitoring tools (CloudWatch, Azure Monitor)

Basic scripting for automation

Practical networking knowledge: running port scans, network mapping (Nmap), identifying simple misconfigurations

Awareness of fundamental protocols (TCP/IP, DNS, HTTP) and common attack vectors

Soft Skills:

Eager to learn and receptive to feedback

Professional, ethical, and able to ask questions when needed

Capable of documenting findings and explaining vulnerabilities to both technical and non-technical audiences

Teamwork and collaboration, following direction well

Experience:

1–3 years of general IT or cybersecurity experience

Certifications (Optional):

While not required, certifications can bolster credibility; hands-on skills are prioritized

Benefits

Immersive cybersecurity training via Evolve Security Academy

Competitive compensation

Healthcare coverage

401(k) match

Flexible paid time off

Hybrid/remote work environment

Annual vacation reimbursement and parental leave

Growth opportunities in a startup-like, high-impact environment

About Evolve Security

Evolve Security provides next-generation cybersecurity services powered by the Darwin Attack® Platform. Services include Attack Surface Management (ASM), Vulnerability Management as a Service (VMaaS), Continuous Penetration Testing (CPT), and cyber advisory. The company also runs Evolve Academy, a top-ranked cybersecurity bootcamp providing hands-on training and real work experience.