Information Security Training Awareness Lead; REMOTE

Position Summary

We are seeking a dynamic and experienced Information Security leader to drive our Information Security Training, Awareness, and Outreach initiatives. This role is critical to strengthening our cybersecurity posture by designing and executing engaging training programs, phishing simulations, and targeted outreach campaigns. The position is full‑time and based in Worcester, MA with options for hybrid or remote work.

• Lead responsibility for significant course development of annual training and awareness plans aligned with regulatory requirements, threat landscape, and organizational goals.
• Lead the design and execution of phishing simulations and insider threat training programs based on NIST standards, acting as a change agent to promote adoption of security and IT best practices across business units.

• Create engaging, multi‑modal training content tailored to diverse learning styles (visual, auditory, kinesthetic) inspired by the current cyber threat landscape.
• Translate complex technical and information security concepts into accessible, actionable learning materials.
• Deliver impactful presentations and facilitate training sessions for audiences at all organizational levels.

• Build an outreach network to serve as liaisons between the Office of the CISO and business units.
• Develop and distribute awareness materials via newsletters, forums, digital signage, and online platforms.
• Establish and maintain an intuitive online hub for training schedules, resources, and security references.
• Respond to active social engineering campaigns to raise awareness and protect The Hanover.

• Develop and maintain key performance indicators and monthly metrics to measure the effectiveness of training, phishing simulations, and outreach efforts.
• Analyze trends and performance data to identify areas for improvement and inform future strategy.
• Collaborate with the GRC team to align reporting with compliance and risk management objectives.
• Prepare and present executive‑level summaries and board communications to highlight program impact and progress.
• Proficiency with automation tools such as "Power BI" is preferred but not required.

• Partner with Legal, HR, SOC, and Corporate Communications teams to address insider threats and develop mitigation strategies.
• Support incident response efforts through targeted education and outreach.
• Promote understanding of IT security responsibilities and organizational policies.

• Bachelor’s degree or 5+ years of relevant experience in cybersecurity, instructional design, or adult education.
• Proficiency in MS Office Suite and familiarity with security training platforms (e.g., Proofpoint).
• Knowledge of cybersecurity frameworks (NIST, ISO, MITRE) is preferred.
• Experience designing and delivering training in virtual and matrixed environments.
• Strong organizational and time‑management skills; ability to adapt and solve problems creatively.
• Skilled in multimedia and web design tools (e.g., Articulate, Captivate, webinar platforms).
• Ability to influence stakeholders and execute strategic plans across a large enterprise.

• SANS Security Awareness Professional (SSAP)
• SANS Managing Human Risk

• Medical, dental, vision, life, and disability insurance
• 401(k) with company match
• Tuition reimbursement
• Paid time off (PTO)
• Company‑paid holidays
• Flexible work arrangements
• Cultural Awareness Day in support of IDE
• On‑site medical/wellness center (Worcester only)

The Hanover values diversity in the workplace and among our customers. The company provides equal opportunity for employment and promotion to all qualified employees and applicants on the basis of experience, training, education, and ability to do the available work without regard to race, religion, color, age, sex/gender, sexual orientation, national origin, gender identity, disability, marital status, veteran status, genetic information, ancestry or any other status protected by law.

Furthermore, The Hanover Insurance Group is committed to providing an equal‑opportunity workplace that is free of discrimination and harassment based on national origin, race, color, religion, gender, ancestry, age, sexual orientation, gender identity, disability, marital status, veteran status, genetic information or any other status protected by law.