Lead Penetration Tester (Dep. Director) New United States (Remote)

Insight Assurance LLC; Lincoln Gardens (FL); Remote; USD 120,000 - 160,000; Full time

Job summary

A leading company in cybersecurity compliance is seeking an experienced Director of Penetration Testing to lead their team. The role includes strategic leadership and overseeing all penetration testing operations, requiring extensive experience and specific certifications. This position offers a competitive salary, professional development opportunities, and a flexible work environment.

Benefits

Competitive Salary

Flexible Paid Time Off

Performance Bonuses

Flexible remote work environment

Opportunities for professional development

Supportive team culture

Qualifications

• Over 5 years of penetration testing experience required.
• Minimum of 3 years managing technical teams in cybersecurity.
• Experience with advanced attack simulations is a plus.

Responsibilities

• Lead and manage the penetration testing department.
• Oversee complex penetration tests on enterprise networks.
• Deliver impactful reports and presentations to stakeholders.

Skills

Penetration Testing

Team Leadership

Risk Analysis

Vulnerability Management

Education

Bachelor’s degree in Cybersecurity or related field

Tools

Metasploit

Burp Suite

OWASP ZAP

Cobalt Strike

Job description

Insight Assurance is considered one of the fastest-growing companies focusing on cybersecurity compliance. The company is a Florida-registered and licensed CPA firm, PCI Qualified Security Assessor (QSA), and ISO 27001 Certification Body founded by former Big-4 professionals (Former EY), looking to simplify the world of IT compliance. With over 20 years of professional experience working with hundreds of organizations from startups to Fortune 500 companies on a variety of engagements, the team at Insight Assurance partners with organizations looking to meet their organizational and compliance goals.

JOB PURPOSE
We are seeking a highly experienced and strategic Director of Penetration Testing to lead our penetration testing department. This leadership role is responsible for overseeing all aspects of the team’s operations, strategy, and technical delivery. The ideal candidate will bring over 5 years of professional experience in penetration testing, including at least 3 years in a leadership or managerial role. The Director will be responsible for building and mentoring a high-performing team, developing testing methodologies, ensuring service excellence, and aligning the team's objectives with broader organizational goals.

KEY RESPONSIBILITIES

Strategic & Team Leadership

Lead and manage the penetration testing department, including hiring, mentoring, performance management, and resource planning

Define departmental goals and key performance indicators in alignment with company objectives

Establish and continuously improve testing methodologies, quality assurance standards, and operational workflows

Serve as the primary point of contact for executive leadership on penetration testing matters

Technical Leadership & Execution

Oversee and participate in complex penetration tests on enterprise networks, systems, applications, and cloud environments

Lead red team engagements, social engineering campaigns, and simulated real-world attacks

Ensure technical accuracy and completeness of all team deliverables and reports

Stay up to date with evolving threat landscapes, attack vectors, and security technologies to continuously innovate service offerings

Stakeholder Communication

Deliver clear, impactful reports and presentations for both technical teams and executive stakeholders

Translate findings into actionable recommendations and risk mitigation strategies

Collaborate with IT, GRC, SOC, and security operations teams to guide remediation efforts

Compliance & Risk

Ensure the team's activities align with industry standards and regulatory frameworks such as PCI-DSS, HIPAA, and NIST

Develop, maintain, and enforce penetration testing policies and procedures

REQUIREMENTS

Education & Experience

Bachelor’s degree in Cybersecurity, Computer Science, Information Technology, or a related field

At least 5 years of hands-on penetration testing experience, including web, network, social engineering, and red team assessments

Minimum 3 years of experience managing or leading technical teams in a cybersecurity context

Proven track record of successfully delivering enterprise-level security testing projects

Experience with exploit development and advanced attack simulation is a plus

Certifications (Required or Strongly Preferred)

OSCP (required)

OSCE, OSWE, OSEP, or similar advanced certifications (preferred)

TECHNICAL SKILLS

Expert-level knowledge of penetration testing tools (e.g., Metasploit, Burp Suite, OWASP ZAP, Cobalt Strike)

Deep understanding of network protocols, operating systems (Windows, Linux), and cloud infrastructure (AWS, Azure, GCP)

Strong command of scripting and programming (Python, Bash, PowerShell, etc.)

Experience with risk analysis and vulnerability management

Exceptional written and verbal communication skills, including the ability to write detailed technical reports for diverse audiences

OTHER REQUIREMENTS

U.S. Citizenship or eligibility to obtain necessary security clearances (if applicable)

Ability to travel up to 25% if needed

Demonstrated leadership, strategic thinking, and ability to operate in a fast-paced environment

High level of integrity and discretion when handling sensitive information

Benefits
- Competitive Salary
- Flexible Paid Time Off and paid holidays
- Performance Bonuses
- Flexible remote work environment
- Opportunities for professional development and growth
- Supportive team culture

Privacy Notice CCPA :

• Insight Assurance shares your personal data/information with Greenhouse recruiting because this is the tool we use for the recruitment process.
• Insight Assurance does not sell personal data/information under any circumstances.
• You may exercise your rights under personal data protection legislation by reaching out to us via: [e-mail] or submit a request via mail at 400 N Tampa St. 15th Floor Suite 122, Tampa, FL 33602

Privacy Notice GDPR:

This notice informs you about the categories of Personal Data/ Information and the Purpose and Scope of Processing Activities to be undertaken by Insight Assurance (we, us, our), under its job application and recruitment process.

We resort to Greenhouse.com as the platform that supports our recruitment process, and therefore your Personal Data/ Information will be Processed on this tool (hosted, shared with, cross-referenced, accessed by our team); we have in place contractual terms and the commitment of Greenhouse.com that ensures the Security and Confidentiality plus Purpose limitation with regards to the Processing of your Personal Data.

When you reply to one of your job postings, you voluntarily and freely submit your Personal Data to us; this, allied with the fact that the Processing by us (and over Greenhouse.com) of that Personal Data has the sole Purpose of validating your application and proceeding with the inherent scrutiny and decision, allows us to argue having Legitimate Interest as the applicable Legal Basis to undertake the Processing of your Personal Data under this scope.

We are a U.S. based company, hence some or all Personal Data pertaining to you will be hosted in the U.S.

The categories of Personal Data under Processing consist of:

• Identification
• Contact
• Education and Professional
• Evaluation

You may exercise several Rights as determined under applicable Personal Data Protection legislation, in short:

• Right of Access – meaning getting information about the Personal Data under Processing by us, except for the information you already know;
• Right of Erasure – you may ask for us to erase all Personal Data pertaining to you under Processing; this may imply you being excluded from the recruitment process, for without information we cannot proceed with it;
• Right of Opposition or Restriction of Processing – you may ask us to stop some Processing or restrict the Processing of some Personal Data, this may imply you being excluded from the recruitment process, at our sole discretion also for without information we cannot proceed with it;
• Rectification – you can rectify your Personal Data at anytime

Apply for this job

*

indicates a required field

First Name *

Last Name *

Email *

Phone *

Resume/CV *

Enter manually

Accepted file types: pdf, doc, docx, txt, rtf

Education

School * Select...

Degree * Select...

Select...

LinkedIn Profile

Fiscal or Tax Residency * Select...

Which country do you currently reside in? * Select...

Years of experience relevant to the position * Select...

Do you have any certifications? *

What is your salary expectation in USD? *