The Director of Information Security is a senior, hands‑on leader responsible for designing, implementing, and operating a comprehensive information security program across three affiliated companies. This role combines technical security leadership, risk management, and governance, risk, and compliance (GRC) oversight.

The ideal candidate is a player‑coach who can lead a small team while remaining deeply engaged in day‑to‑day security operations and architecture. This individual will serve as a trusted advisor to business leaders, management, and external clients, translating complex security risks into clear, actionable business terms. Lead and manage a small, highly technical information security team, providing mentorship, direction, and hands‑on support.

Design, implement, and maintain security controls across identity, endpoint, network, cloud, and SaaS environments.

Provide direct technical oversight and escalation support for security incidents, investigations, and response activities.

Ensure consistent security posture and standards across three separate companies while accommodating business‑specific needs. Act as a subject matter expert and hands‑on contributor for core security platforms, including:

Identity & Access Management:

Okta, Azure AD

Network & Cloud Security:

Zscaler, Azure

Productivity & SaaS Security:

Microsoft 365

Email Security:

Proofpoint

Endpoint Protection:

CrowdStrike

Security Monitoring & SIEM:

Splunk Partner with IT and engineering teams to securely design and deploy cloud and hybrid environments.

Continuously evaluate and enhance security tooling, configurations, and detection capabilities. Lead enterprise security risk assessments to identify, analyze, prioritize, and document information security risks.

Clearly communicate risk exposure and mitigation strategies to non‑technical business users, executive management, and clients.

Drive risk remediation efforts, tracking progress and ensuring accountability.

Integrate security risk management into broader enterprise risk management processes. Own and operate the information security governance program, including policies, standards, procedures, and metrics.

Ensure the design and effectiveness of IT General Controls (ITGCs).

Support internal and external audits, including planning, evidence collection, remediation, and ongoing control improvements.

Maintain compliance with applicable regulatory and contractual requirements, with emphasis on: State Department of Insurance (DOI) data security regulations

New York Department of Financial Services (NYDFS) 23 NYCRR 500 Partner with Legal, Compliance, and Audit teams to ensure alignment between security, regulatory, and business objectives. Serve as a key security liaison for: Non‑technical business staff

Executive and senior management

External clients, partners, and auditors Translate technical security concepts into clear, business‑focused language appropriate for each audience.

Prepare and deliver security briefings, risk summaries, and compliance updates to leadership.

Demonstrate commitment to Company's Code of Business Conduct and Ethics, and apply knowledge of compliance policies and procedures, standards and laws applicable to job responsibilities in the performance of work. Bachelor's degree in Information Security, Computer Science, Information Systems, or a related field (or equivalent experience).

8+ years of progressive experience in information security, including leadership or senior technical roles.

Proven experience managing and mentoring small security teams.

Strong hands‑on technical expertise in: Okta, Zscaler, Azure, Microsoft 365

Proofpoint, CrowdStrike, Splunk Demonstrated experience leading security risk assessments and remediation initiatives.

Strong background in governance, risk, and compliance, including IT general controls and audit support.

Experience working in regulated environments, preferably financial services or insurance. Preferred Qualifications Prior experience supporting State Department of Insurance data security regulations.

Direct experience with

NYDFS 23 NYCRR 500

compliance.

Audit background (internal audit, external audit, or security assurance).

Relevant certifications such as CISSP, CISM, CRISC, CGEIT, or similar. Key Competencies & Attributes Hands‑on, pragmatic security leader with a strong bias toward execution.

Excellent verbal and written communication skills.

Ability to balance security rigor with business enablement.

Strong organizational and prioritization skills across multiple companies and stakeholders.

High integrity, sound judgment, and comfort operating with limited oversight.