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Remote Penetration Testing Jobs in Chicago, IL (NOW HIRING)

Synack

Regional Sales Director

Chicago, IL · On-site +1

Synack's Penetration Testing as a Service platform manages customers' attack surfaces by ... This is a remote position and qualified candidates must be located in the Chicago Metro Area.

All JobsPenetration Testing JobsRemote Penetration Testing JobsRemote Penetration Testing Jobs in Chicago, IL

Remote Penetration Testing information

See Chicago, IL salary details

$23.2K

$123.5K

$173.6K

How much do remote penetration testing jobs pay per year?

As of Aug 9, 2026, the average yearly pay for remote penetration testing in Chicago, IL is $123,509.00, according to ZipRecruiter salary data. Most workers in this role earn between $98,900.00 and $145,200.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a remote penetration tester?

To thrive as a Remote Penetration Tester, you need a solid understanding of computer networks, cybersecurity principles, and common vulnerabilities, often supported by a degree in computer science or related certifications like OSCP or CEH. Familiarity with penetration testing tools such as Metasploit, Burp Suite, Nmap, and various operating systems is essential. Strong analytical thinking, attention to detail, and clear written communication skills help you effectively discover, document, and explain security findings to clients. These competencies are crucial for accurately identifying risks and helping organizations strengthen their security posture.

Is there a demand for remote penetration testing?

Remote penetration testing is in high demand as organizations seek cybersecurity professionals to identify vulnerabilities remotely. Skills in network security, ethical hacking, and familiarity with tools like Kali Linux and Metasploit are essential, and many companies prefer candidates with industry certifications such as OSCP or CEH.

What is the difference between Remote Penetration Testing vs Vulnerability Assessment Specialist?

AspectRemote Penetration TestingVulnerability Assessment Specialist
CertificationsOSCP, CEH, GPENOSCP, CEH, CISSP
Work EnvironmentHands-on testing, simulated attacksScanning, identifying vulnerabilities
Industry UsageCybersecurity firms, IT departmentsSecurity teams, consulting firms

Remote Penetration Testing involves actively exploiting vulnerabilities to assess security defenses, while Vulnerability Assessment Specialists focus on identifying and prioritizing security weaknesses without exploiting them. Both roles require similar certifications and often work in overlapping environments, but penetration testers perform more in-depth, simulated attack scenarios to evaluate security robustness.

What are some common challenges faced by remote penetration testers, and how can they be addressed?

Remote penetration testers often encounter challenges such as limited access to physical infrastructure, varying levels of client preparedness, and potential communication barriers with on-site teams. To address these issues, it's important to establish clear communication channels, use secure remote access tools, and maintain detailed documentation of testing activities. Building strong relationships with client IT staff and staying up-to-date with remote testing best practices can also help ensure effective and successful engagements.

Can remote penetration testers work remotely?

Yes, remote penetration testers can work remotely, as the role primarily involves using specialized tools and techniques to assess cybersecurity defenses from any location. Many companies hire remote testers to perform assessments, provided they have the necessary skills, secure access, and appropriate certifications such as OSCP or CEH. Effective communication and familiarity with remote collaboration tools are also important for success in remote roles.

What is remote penetration testing?

Remote penetration testing is a security assessment process where cybersecurity professionals, also known as ethical hackers, attempt to find and exploit vulnerabilities in an organization’s systems, networks, or applications from an offsite location. This simulates a real-world cyberattack to help organizations identify and fix security weaknesses before malicious actors can exploit them. Remote penetration testing is often conducted over the internet, making it a flexible and efficient option for businesses to assess their security posture without requiring onsite visits.
What are the most commonly searched types of Penetration Testing jobs in Chicago, IL? The most popular types of Penetration Testing jobs in Chicago, IL are:
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What cities near Chicago, IL are hiring for Remote Penetration Testing jobs? Cities near Chicago, IL with the most Remote Penetration Testing job openings:
Remote Penetration Testing jobs near you
Infographic showing various Remote Penetration Testing job openings in Chicago, IL as of August 2026, with employment types broken down into 77% Full Time, and 23% Part Time. Highlights an 100% Remote job distribution, with an average salary of $123,509 per year, or $59.4 per hour.

Solutions Engineer, Penetration Testing

Prescient Security

Chicago, IL • Remote

$130K/yr

Full-time

Posted 5 days ago

Job description

Solutions Engineer 

Remote, US 


At Prescient Security, we are on a mission to simplify security and compliance.


Our core values are:

  • Bring Order to Chaos
  • Be Accountable & See it Through
  • 1000% With You
  • Support & Collaborate
  • Think Outside the Box



Summary 

The Solutions Engineer partners with Sales and clients to design technical solutions that align customer requirements with Prescient Security’s service offerings. This role serves as a trusted technical advisor throughout the sales process, leading discovery, developing solution recommendations, defining project scope, and ensuring a smooth transition from sales to delivery. 


Key Responsibilities 

  • Partner with Sales to support client meetings, technical discovery, and solution presentations. 
  • Understand customer business and technical requirements and recommend appropriate security services and solutions. 
  • Develop accurate project scopes, estimates, assumptions, and Statements of Work (SOWs). 
  • Serve as the technical subject matter expert during the pre-sales process, including penetration testing, compliance, and security assessment services. 
  • Collaborate with Project Management and Delivery teams to ensure successful project handoff and execution. 
  • Identify technical risks, recommend solutions, and ensure proposed engagements are aligned with customer needs and delivery capabilities. 
  • Build trusted relationships with clients by providing technical guidance and responding to questions throughout the sales cycle. 
  • Contribute to the continuous improvement of sales collateral, solution offerings, and scoping processes. 


Qualifications 

  • Experience in solutions engineering, solutions architecture, sales engineering, cybersecurity consulting, or a related technical role. 
  • Strong understanding of cybersecurity concepts, security assessments, penetration testing, and compliance frameworks. 
  • Excellent communication, presentation, and client-facing skills. 
  • Experience creating Statements of Work (SOWs), technical proposals, or solution designs. 
  • Ability to manage multiple opportunities in a fast-paced environment while partnering across Sales, Delivery, and Operations. 


The base salary is $130,000.00USD. Your base salary will be determined based on your location, experience, and the pay of employees in similar positions.


NOTE: This job description is not intended to be all-inclusive. Employee may perform other related duties as negotiated to meet the ongoing needs of the organization.

Prescient Security provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age disability or genetics.