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Offensive Security Engineer Remote Jobs in Springfield, MA

Senior Operational Engineer

Hartford, CT · Remote

$105K - $144K/yr

At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security ... Experience working within Agile delivery frameworks and collaborating with distributed or remote ...

Senior Operational Engineer

Hartford, CT · Remote

$105K - $144K/yr

At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security ... Experience working within Agile delivery frameworks and collaborating with distributed or remote ...

PAM Senior Manager

Hartford, CT · On-site +1

$112K - $151K/yr

Bachelor's degree in Computer Science, Cybersecurity, Information Security, Engineering ... remote access. Overseeing multiple concurrent engagements, including scope, staffing, budgets ...

Staff Site Reliability Engineer

OR · Remote

$53.50 - $71/hr

LOCATION 100% Remote - Anywhere within the US RESPONSIBILITIES * Design, improve, and maintain ... For added security, where possible, apply through our company website at finalsite.com/jobs.

Staff Site Reliability Engineer

Glastonbury, CT · Remote

$58.25 - $77.50/hr

LOCATION 100% Remote - Anywhere within the US RESPONSIBILITIES * Design, improve, and maintain ... For added security, where possible, apply through our company website at finalsite.com/jobs.

Staff Site Reliability Engineer

Glastonbury, CT · On-site +1

$57 - $75.75/hr

LOCATION 100% Remote - Anywhere within the US RESPONSIBILITIES * Design, improve, and maintain ... For added security, where possible, apply through our company website at finalsite.com/jobs.

Salary range is subject to location, as this role can be remote. Roles and Responsibilities ... Partner with IT architecture, security, infrastructure, data, and application teams, to ensure ...

This role is fully remote, with no regular in-office requirement. The Contributions You'll Make ... Ensure AI solutions comply with enterprise standards for security, privacy, governance, and ...

AVP, Software Engineering Lead

Hartford, CT · On-site +1

$182K - $273K/yr

... Security, Risk, and Business leaders. The AVP will drive the modernization of engineering practices ... This role can have a Hybrid or Remote work schedule. Candidates who live near one of our office ...

AVP, Software Engineering Lead

Hartford, CT · On-site +1

$255K/yr

... Security, Risk, and Business leaders. The AVP will drive the modernization of engineering practices ... This role can have a Hybrid or Remote work schedule. Candidates who live near one of our office ...

Staff Site Reliability Engineer

Glastonbury, CT · On-site +1

$57 - $75.75/hr

LOCATION 100% Remote - Anywhere within the US WHAT WE LOOK FOR * Cloud Architecture & Scalability ... Security-First Engineering . You bring a security-first mindset to everything you build, treating ...

Staff Site Reliability Engineer

Glastonbury, CT · Remote

$58.25 - $77.50/hr

LOCATION 100% Remote - Anywhere within the US WHAT WE LOOK FOR * Cloud Architecture & Scalability ... Security-First Engineering . You bring a security-first mindset to everything you build, treating ...

Structures - Rail Project Engineer

East Hartford, CT · On-site +1

$78K - $105K/yr

... security, and professional growth, including: * Competitive medical, dental, and vision coverage ... Flexible work arrangements, including hybrid and remote opportunities where business needs allow

... security, and professional growth, including: * Competitive medical, dental, and vision coverage ... Flexible work arrangements, including hybrid and remote opportunities where business needs allow

Showing results 21-40

Offensive Security Engineer Remote information

See Springfield, MA salary details

$61.3K

$152.2K

$204.8K

How much do offensive security engineer remote jobs pay per year?

As of Sep 15, 2026, the average yearly pay for offensive security engineer remote in Springfield, MA is $152,239.00, according to ZipRecruiter salary data. Most workers in this role earn between $142,500.00 and $157,900.00 per year, depending on experience, location, and employer.

What does an offensive security engineer do?

An Offensive Security Engineer is responsible for proactively identifying and mitigating security vulnerabilities in an organization’s systems, networks, and applications. Working remotely, they perform penetration testing, vulnerability assessments, and simulated cyberattacks to discover weaknesses before malicious actors can exploit them. They also provide detailed reports and recommendations to help organizations improve their overall security posture. Remote Offensive Security Engineers use a variety of tools and collaborate with other security professionals to ensure effective communication and secure operations across distributed environments.

What are the key skills and qualifications needed to thrive as an offensive security engineer?

To thrive as an Offensive Security Engineer (Remote), you need strong expertise in penetration testing, vulnerability assessment, and cybersecurity principles, often supported by a degree in computer science or a related field. Familiarity with tools like Metasploit, Burp Suite, and Kali Linux, as well as certifications such as OSCP or CEH, is typically required. Attention to detail, problem-solving skills, and effective written communication are critical soft skills for success in this role. These abilities are essential for identifying vulnerabilities, reporting findings clearly, and helping organizations strengthen their security posture against evolving threats.

What are some common challenges faced by remote offensive security engineers, and how can they be addressed?

Remote Offensive Security Engineers often face challenges such as coordinating effectively with geographically dispersed teams, maintaining secure access to sensitive systems, and staying updated on rapidly evolving threat landscapes. Overcoming these hurdles typically involves strong communication skills, leveraging secure collaboration tools, and establishing regular check-ins with colleagues. Additionally, continuous learning through online resources and industry forums is vital to remain effective and proactive in identifying and addressing security vulnerabilities.

What is the difference between Offensive Security Engineer Remote vs Penetration Tester?

AspectOffensive Security Engineer RemotePenetration Tester
CertificationsOSCP, OSWE, CEHOSCP, CEH, GPEN
Work EnvironmentRemote, collaborative security teamsOften client-site or remote assessments
Industry UsageSecurity teams, cybersecurity firmsConsulting firms, security assessments
Search & Comparison IntentUnderstanding roles, skills, and remote opportunitiesJob scope, certifications, and remote work options

Offensive Security Engineer Remote and Penetration Tester roles share overlapping skills and certifications like OSCP and CEH. However, Offensive Security Engineers typically work within security teams on ongoing security infrastructure, often remotely, focusing on offensive security strategies. Penetration Testers usually perform specific security assessments, sometimes on-site, and may have a broader consulting focus. Both roles are vital in cybersecurity but differ in scope and work environment.

What are popular job titles related to Offensive Security Engineer Remote jobs in Springfield, MA?

For Offensive Security Engineer Remote jobs in Springfield, MA, the most frequently searched job titles are:

What cities near Springfield, MA are hiring for Offensive Security Engineer Remote jobs?

Cities near Springfield, MA with the most Offensive Security Engineer Remote job openings:

Infographic showing various Offensive Security Engineer Remote job openings in Springfield, MA as of June 2026, with employment types broken down into 88% Full Time, 4% Part Time, and 8% Contract. Highlights an 41% Physical, 2% Hybrid, and 57% Remote job distribution, with an average salary of $152,239 per year, or $73.2 per hour.

Senior Operational Engineer

Hartford, CT • Remote

Sun Life Financial
Insurance Carriers • 10K+ employees

$105K - $144K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 25 days ago


Sun Life Assurance Company of Canada rating

8.6

Company rating: 8.6 out of 10

Based on 18 frontline employees who took The Breakroom Quiz


Job description

Sun Life U.S. is one of the largest providers of employee and government benefits, helping approximately 50 million Americans access the care and coverage they need. Through employers, industry partners and government programs, Sun Life U.S. offers a portfolio of benefits and services, including dental, vision, disability, absence management, life, supplemental health, medical stop-loss insurance, and healthcare navigation. We have more than 6,400 employees and associates in our partner dental practices and operate nationwide.


At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring, and impactful.


When you join Sun Life, you'll work with passionate colleagues and empowering leaders who support your growth and celebrate your contributions, so you can make a meaningful difference in our Clients' lives.


Visit our website to discover how Sun Life is making life brighter for our customers, partners and communities.

Job Description:

Sun Life is seeking a highly skilled Senior Operational Engineer to join the Contact Centre Infrastructure Operations (CCIO) team. This team is responsible for the design, delivery, operational support, and continuous improvement of enterprise telephony and contact centre platforms.

As a senior technical contributor with an AI-forward mindset, you will play a key role in modernizing and supporting Sun Life's communication infrastructure, including Microsoft Teams Telephony and Amazon Connect Contact Centre Services. You will work closely with business stakeholders, architects, engineers, and operational teams to design scalable solutions, drive innovation, and enhance the employee and client experience through cloud and AI-enabled technologies.

This role combines solution design, operational excellence, and strategic technology modernization within a highly regulated financial services environment.

What will you do?

  • Partner with business teams to plan, prioritize, and execute migration initiatives supporting the modernization of Financial Centres onto Microsoft Teams Telephony.
  • Collaborate with business stakeholders, business systems analysts, architects, and technology partners to gather requirements, refine solutions, and develop innovative telephony and AI-enabled capabilities.
  • Help to support scalable, secure, and supportable cloud-based solutions that align with enterprise architecture, security, and governance standards.
  • Develop High-Level Designs (HLDs), detailed technical designs, and implementation approaches for telephony and cloud infrastructure solutions.
  • Support and enhance Amazon Connect and associated AWS services from an operational perspective, ensuring platform reliability, resilience, and performance.
  • Participate in Agile delivery teams and contribute to DevOps practices, including continuous integration, continuous deployment, infrastructure automation, and platform monitoring.
  • Identify opportunities to leverage artificial intelligence, automation, and cloud-native services to improve operational efficiency and client experience.
  • Provide subject matter expertise and mentoring to operations teams, promoting knowledge sharing through technical coaching and documentation.
  • Create and maintain operational procedures, knowledge articles, standards, and support documentation.
  • Continuously evaluate emerging technologies, industry trends, and AI capabilities to identify opportunities for innovation and process improvement.
  • Participate in incident response, change management, and operational support activities to maintain service stability and availability.

What you will need to succeed

Required Qualifications

  • Bachelor's degree in Computer Science, Engineering, Information Technology, or equivalent combination of education and relevant industry experience.
  • 3-5 years of experience designing, delivering, and supporting cloud-based technology solutions.
  • 2+ years of hands-on experience supporting AWS services and enterprise telephony platforms, preferably Amazon Connect and/or Microsoft Teams Telephony.
  • Experience developing and supporting AWS Lambda solutions using Python.
  • Demonstrated understanding of cloud architecture principles and AWS service capabilities.
  • Experience working within regulated environments where security, privacy, compliance, and risk management are critical considerations.
  • Knowledge of ITIL practices, including incident, problem, and change management processes.
  • Experience working within Agile delivery frameworks and collaborating with distributed or remote teams.
  • Experience managing and supporting AWS environments and cloud infrastructure.
  • Experience with DevOps practices and tools such as Terraform, Jenkins, Bitbucket, Ansible, and CI/CD pipelines.
  • Demonstrated AI mindset, including curiosity, experimentation, and practical application of AI and automation technologies to solve business problems.

Preferred Qualifications

  • Strong verbal and written communication skills with the ability to present technical concepts to both technical and non-technical audiences.
  • Experience designing, implementing, or supporting AI-enabled solutions within cloud environments.
  • Strong analytical and problem-solving skills with a focus on operational excellence and continuous improvement.
  • Knowledge of modern contact centre architectures, customer experience platforms, and telephony technologies.
  • Experience with AWS AI and machine learning services such as Amazon Lex, SageMaker, Comprehend, Bedrock, or related technologies.
  • Proven ability to identify opportunities for automation and leverage emerging technologies to improve business outcomes.
  • Self-driven and adaptable, with the ability to manage competing priorities in a fast-paced and evolving environment.
  • Strong collaboration and relationship-building skills with the ability to influence through technical expertise.
  • Commitment to continuous learning and staying current on cloud, AI, automation, and telephony industry trends.

Salary Range: $91,000 - $136,500
At our company, we are committed to pay transparency and equity. The salary range for this role is competitive nationwide, and we strive to ensure that compensation is fair and equitable. Your actual base salary will be determined based on your unique skills, qualifications, experience, education, and geographic location. In addition to your base salary, this position is eligible for a discretionary annual incentive award based on your individual performance as well as the overall performance of the business. We are dedicated to creating a work environment where everyone is rewarded for their contributions.

Not ready to apply yet but want to stay in touch? Join our talent community to stay connected until the time is right for you!

We are committed to fostering an inclusive environment where all employees feel they belong, are supported and empowered to thrive. We are dedicated to building teams with varied experiences, backgrounds, perspectives and ideas that benefit our colleagues, clients, and the communities where we operate. We encourage applications from qualified individuals from all backgrounds.

Life is brighter when you work at Sun Life

At Sun Life, we prioritize your well-being with comprehensive benefits, including generous vacation and sick time, market-leading paid family, parental and adoption leave, medical coverage, company paid life and AD&D insurance, disability programs and a partially paid sabbatical program. Plan for your future with our 401(k) employer match, stock purchase options and an employer-funded retirement account. Enjoy a flexible, inclusive and collaborative work environment that supports career growth. We're proud to be recognized in our communities as a top employer. Proudly Great Place to Work Certified in Canada and the U.S., we've also been recognized as a "Top 10" employer by the Boston Globe's "Top Places to Work" for two years in a row. Visit our website to learn more about our benefits and recognition within our communities.

We will make reasonable accommodations to the known physical or mental limitations of otherwise-qualified individuals with disabilities or special disabled veterans, unless the accommodation would impose an undue hardship on the operation of our business. Please email thebrightside@sunlife.comto request an accommodation.

For applicants residing in California, please read our employee California Privacy Policy and Notice.

We do not require or administer lie detector tests as a condition of employment or continued employment.

Sun Life will consider for employment all qualified applicants, including those with criminal histories, in a manner consistent with the requirements of applicable state and local laws, including applicable fair chance ordinances.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran.

Job Category:

IT - Technology Services

Posting End Date:

18/09/2026

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