Penetration Tester

Sky is the tech media company that makes entertainment and connectivity a personal, simple, and seamless experience.

Our mottois We Believe in Better: we believe people deserve the best, and every day we innovate to create value and make our customers’ lives easier.

We are part of Sky Group and the Comcast family , operating within an international environment focused on continuous innovation and powered by world-class technology that enables us to reach millions of people every day.

With an IP-first approach, we design cutting-edge technology platforms such as Sky Stream, Sky Q, Sky Glass, and NOW, bringing together premium content, trusted and always-on news coverage, and major sporting events within a simple and intuitive ecosystem.

We connect with audiences across the entire country through our free-to-air channels – TV8, Cielo, and Sky TG24 – and go beyond entertainment with Sky Wifi and Sky Mobile , delivering ultra-fast connectivity both at home and on the go.

This is how we bring the joy of a better experience , guided by our values :

• Creative . We are ambitious and innovative, embracing new technologies and leveraging insights to stay ahead of the curve, continuously raising the bar for our customers.
• Welcoming . We are inclusive, collaborative, and respectful, fostering a strong sense of belonging.
• Simplifying . We focus on what truly matters, set clear priorities, bring clarity, and remove complexity.
• Do the Right Thing. We build a culture founded on clarity, fairness, and trust through transparent processes and decisions that people can rely on.

As a Penetration Tester, you will be responsible for identifying, assessing, and validating security vulnerabilities in Sky Italy applications, systems, networks, and cloud environments. You will also play an active role in supporting the remediation process, working alongside relevant teams to ensure vulnerabilities are properly understood, prioritised, and fixed. This role requires solid technical expertise, strong analytical thinking, and the ability to collaborate effectively with both technical and non-technical stakeholders within region and at Group level, translating complex security findings into clear, actionable insights for audiences at different levels of the organisation.

What you’ll do:

• Plan, prepare and execute penetration testing activities on Sky Italy applications, systems, networks, and cloud environments.
• Identify, verify, and validate vulnerabilities using both manual techniques and automated tools.
• Simulate real-world attack scenarios to assess the effectiveness of existing security controls.
• Document findings clearly, including technical details, potential impact, and risk severity.
• Produce detailed reports and present results to both technical and non-technical stakeholders.
• Support the remediation process to ensure vulnerabilities are properly understood, prioritised, and fixed.
• Proactively stay up to date with emerging threats, vulnerabilities, and attack techniques.
• Contribute to the continuous improvement of internal security testing methodologies and best practices.
• Support security incident management.
• Support application security management.
• Work closely with Group in defining offensive strategy to be implemented locally in the region.

What we’re looking for:

• Master’s degree in Computer Science or Computer Engineering, or equivalent experience.
• Proven experience as a Penetration Tester and/or Red Teamer in complex environments.
• Solid understanding of common vulnerabilities and attack techniques.
• Hands‑on experience with standard penetration testing tools (e.g. Nmap, Burp Suite, Metasploit, Kali Linux).
• Experience with Active Directory configuration review.
• Solid knowledge of networking, operating systems, web/cloud architectures, and security fundamentals.
• Strong analytical and problem‑solving skills, with a methodical approach to identifying and validating vulnerabilities.
• English: B2 level or above, both written and spoken.
• Proactivity and a strong problem‑solving mindset.
• Excellent communication skills for interacting with both technical and non‑technical stakeholders.

Preferred Qualifications:

• Cyber security certifications (e.g. OSCP, OSWE, or equivalent).
• Familiarity with DevSecOps practices and integrating security into CI/CD pipelines.
• Contributions to the security community (e.g. CTF participation, blog posts, open-source tools, conference talks).

What we offer:

Under the Private Radio and Television Industry Collective Labour Agreement ( CCNL ), the salary for this position starts from €40,000 . Contract

Type: Permanent Contract

The actual compensation package will be determined based on the candidate’s experience and specific skills. The position is also eligible for the annual incentive scheme .

At Sky, we believe in providing a healthy, stimulating and inclusive work environment that supports individual needs both professionally and personally. With this in mind, we have created Sky4You , our wellbeing programme designed to support people through the different stages of their lives. Some of the benefits available to you include:

• Free access to Sky TV services through Sky Q or Sky Stream Sky Wifi and Sky Mobile at exclusive employee rates
• Private health insurance, extendable to family members and cohabiting partners Life and accident insurance coverage
• Free access to the company gym (Milan office only)
• Financial support for new parents and caregivers
• Free assistance with annual tax returns

In addition, we offer initiatives focused on physical, mental and financial wellbeing, summer camps and language courses for children’s employees, as well as a wide range of employee discounts and exclusive offers.

Hybrid Working

Depending on your role, you may benefit from up to 12 days of remote working per month , giving you the flexibility to focus without distractions. At the office, you'll have the opportunity to collaborate, co-create, and make decisions alongside your colleagues in unique spaces designed to help you perform at your best. Our Milan hub is located in Rogoredo , in the Santa Giulia district, just a few minutes' walk from Milano Rogoredo Station (M3 Rogoredo FS, regional and high-speed trains, and the Passante railway network). The area is also well served by bus connections and easily accessible by car and motorcycle , thanks to its convenient links to the city's main transport routes. At Sky Campus , you'll find:Two cafés A company restaurant The Sky Cinema A variety of collaborative spaces dedicated to innovation and idea sharingThe surrounding area also offers a wide range of amenities, including cafés, restaurants, supermarkets, and other everyday services.

Learning & Development:

At Sky , we invest in your growth. We believe that internal mobility is a powerful driver of professional development and offer opportunities to explore new roles and career paths across the organization. Through Sky Learn , our learning platform, you'll have access to continuous training, digital learning content, and upskilling and reskilling programmes designed to help you grow, evolve, and build your future career.

Social Impact & Inclusion:

At Sky , we believe in people. We are committed to creating a diverse, equitable and inclusive workplace where everyone can feel valued, be themselves, and reach their full potential. We actively promote wellbeing and ensure equal opportunities for all , including individuals belonging to protected categories under Italian Law 68/99 . To support this commitment, Sky hosts several employee networks, including Body&Mind , LGBTQ+ , Visualizzare la mail su click.jobroute.io , and Parents&Carers . These voluntary communities bring colleagues together to share experiences and promote initiatives focused on wellbeing, inclusion, and female empowerment. We work every day to create a positive and lasting impact on the communities around us through Sky Cares volunteering initiatives, Sky Up digital education programmes, and the immersive company-visit experiences offered through the Academy Studios . At Sky, everyone belongs, everyone can grow, and everyone can make a difference.

At Sky, ideas become experiences enjoyed by millions of people.

Sky is committed to attracting and supporting talent in all its forms. All applications, including those from individuals belonging to protected categories under Italian Law 68/99, will be considered in accordance with equal opportunity and inclusion principles, without discrimination of any kind. Sky Italia is committed to ensuring a fair, inclusive and non-discriminatory recruitment process.In line with this commitment and with Legislative Decree 96/2026, Sky Italia does not request or collect information regarding candidates’ previous compensation or employment classification, either during interviews or through direct contacts and/or third parties involved in the recruitment process.