Red Team Penetration Tester - Technical Lead (In Office or Remote)

Sorry, this job was removed at 02:18 p.m. (UTC) on Friday, Sep 26, 2025
2 Locations
In-Office or Remote
150K-224K Annually
Financial Services
The Role

At Freddie Mac, our mission of Making Home Possible is what motivates us, and it’s at the core of everything we do. Since our charter in 1970, we have made home possible for more than 90 million families across the country. Join an organization where your work contributes to a greater purpose.

Position Overview:

The Freddie Mac Red Team is responsible to test the overall strength of our organization’s defenses (the technology, the processes, and the people) by simulating the objectives and actions of an attacker. We are seeking an Information Security Tech Lead to assist the team by providing subject matter expertise in Penetration testing of Infrastructure and Networks, Web Applications, Cloud and Social engineering, and Purple Team. In this role, the candidate will provide enhanced vulnerability analysis and contextual feedback to stakeholders to support the resolution of discovered vulnerabilities and facilitate risk awareness.

Responsibilities include:

Penetration Testing and Red Team assessments

  • Simulate real-world threat actors targeting the organization’s people, processes, and technology to expose risk within the environment.

  • Develop custom exploits, tooling, and infrastructure to evade defensive controls and further team objectives.  

  • Go beyond Nessus scanning to lead red team assessments and penetration tests playing a critical role in their success.

  • Work closely with defensive analysts to update detections and ensure adequate coverage after an operation is complete.

  • Collaborate with stakeholders to scope prospective engagements and provide thorough out briefings after assessments are complete. Provide guidance on vulnerability remediation and track progress through to completion.

  • Contribute to the development and improvement of security policies, standards, and guidelines.

  • Demonstrate a team-oriented mindset adept at learning the latest technologies; train and mentor less experienced team members on penetration tactics and techniques.

Develop Team Capabilities and Leadership

  • Generate innovative ideas and challenge the status quo

  • Develop scripts, tools, or methodologies to enhance the Red teaming processes and capabilities

  • Participate in and actively support mentoring with other members of the team

  • Assist with scoping prospective engagements, leading engagements from kickoff through remediation, and mentoring less experienced staff

Our Impact:

The Red team is responsible for testing the overall strength of our organization’s defenses (the technology, the processes, and the people) by simulating the objectives and actions of an attacker!

Your Impact:

This role provides domain expertise in Penetration testing of Infrastructure and Networks, Web Applications, Cloud and Social engineering, as well as Red Team and Purple Team internal engagements. Additionally, you will provide improved vulnerability analysis and contextual feedback to partners to support the resolution of discovered vulnerabilities and facilitate risk awareness.

Qualifications

  • 8-10 years of relevant experience performing penetration testing, offensive security assessments, Purple Team engagements.

  • One or more technical certifications: OSCP, OSWE, OSED, OSEP, OSEE, GPEN, CRTO, GXPN, or similar.

  • Experience with one or more Object Oriented language (C/C++, C#, Go, etc).

  • Working knowledge of one or more scripting language (Python, PowerShell, BASH, etc.).

  • Experience bypassing modern defensive controls such as EDRs, network defenses, email filters, etc.

  • Experience creating custom tools and modifying existing tools to automate workflows and simulate threat actor activities.

  • Experience hunting for vulnerabilities and developing exploits.

  • In depth knowledge of cloud technologies as it relates to crafting red team infrastructure, and offensive security testing.

  • Advanced usage of Cobalt Strike or similar C2 framework including creation of Aggressor Scripts, Beacon Object Files (BOF), and associated infrastructure.

  • Must be willing to work east coast hours

Key to success in this role

  • Leadership

  • Strong communication skills

  • Ability to work independently, as well as effectively work in teams with individuals with a variety of skills and backgrounds

Current Freddie Mac employees please apply through the internal career site.

We consider all applicants for all positions without regard to gender, race, color, religion, national origin, age, marital status, veteran status, sexual orientation, gender identity/expression, physical and mental disability, pregnancy, ethnicity, genetic information or any other protected categories under applicable federal, state or local laws. We will ensure that individuals are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.

A safe and secure environment is critical to Freddie Mac’s business. This includes employee commitment to our acceptable use policy, applying a vigilance-first approach to work, supporting regulatory mandates, and using best practices to protect Freddie Mac from potential threats and risk. Employees exercise this responsibility by executing against policies and procedures and adhering to privacy & security obligations as required via training programs.

CA Applicants:  Qualified applications with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act.

Notice to External Search Firms: Freddie Mac partners with BountyJobs for contingency search business through outside firms. Resumes received outside the BountyJobs system will be considered unsolicited and Freddie Mac will not be obligated to pay a placement fee. If interested in learning more, please visit www.BountyJobs.com and register with our referral code: MAC.

Time-type:Full time

FLSA Status:Exempt

Freddie Mac offers a comprehensive total rewards package to include competitive compensation and market-leading benefit programs. Information on these benefit programs is available on our Careers site.

This position has an annualized market-based salary range of $150,000 - $224,000 and is eligible to participate in the annual incentive program. The final salary offered will generally fall within this range and is dependent on various factors including but not limited to the responsibilities of the position, experience, skill set, internal pay equity and other relevant qualifications of the applicant.

Freddie Mac Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Freddie Mac and has not been reviewed or approved by Freddie Mac.

  • Healthcare Strength Health, dental, and vision insurance are consistently described as core offerings, supported by disability and life insurance coverage. Wellbeing support is reinforced through resources like a wellness center and related health programs.
  • Retirement Support Retirement benefits are positioned as a standout element, including a 401(k) with a strong match structure and additional retirement-related features. Profit sharing and pension-plan references further increase the perceived depth of long-term financial support.
  • Parental & Family Support Family-oriented benefits are described as extensive, including paid leave for new mothers and parental leave for spouses/domestic partners. Fertility coverage, adoption/surrogacy reimbursement, and back-up child/elder care add practical support across multiple family needs.

Freddie Mac Insights

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The Company
HQ: McLean, VA
9,809 Employees
Year Founded: 1970

What We Do

Freddie Mac is serving America’s homebuyers, homeowners and renters by financing the creation and preservation of more affordable homeownership and rental opportunities, providing liquidity, stability and affordability to the housing market. We are Making Home Possible for families across the nation.

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