Director Of IT Security — Directive Consulting is the leading B2B marketing agency for brands that are responsible about the metrics that matter most. Performance , Communications , and Commerce , all wired to share intelligence and answer to revenue. This role reports to the Head of Finance and is responsible for leading Directive's information security strategy across our fully remote workforce operating in the United States, Canada, Mexico and the United Kingdom.

As the Director of IT Security, you will establish and continuously mature our cybersecurity program, protecting our people, client data, business operations and technology ecosystem from evolving cyber threats. You will proactively identify and mitigate cyber risks, strengthen our security posture, oversee compliance initiatives and prepare the organization to respond effectively to evolving threats.

Cybersecurity Strategy And Governance

Develop and execute the company's information security strategy and scalable security roadmap. Establish and maintain enterprise security policies, standards and governance frameworks. Present cybersecurity risks, recommendations and security metrics to executive leadership. Stay ahead of emerging cybersecurity threats, AI risks and industry best practices.

Risk Management And Threat Assessments

Conduct ongoing enterprise‑wide cybersecurity risk assessments across infrastructure, endpoints, applications and business processes. Build and maintain the organization's cybersecurity risk register and remediation roadmap. Lead vulnerability management efforts and prioritize remediation based on business risk.

Perform third‑party vendor security assessments and ongoing vendor risk management. Configure and enforce data governance policies across distributed tools (Notion, Drive, Stratos) to prevent data silos. Manage device security policies using MDM software (Kandji) to protect company assets.

Partner with the Senior IT Manager to implement technical security controls and monitor the health of the environment.



Own customer security questionnaires and support enterprise sales opportunities by demonstrating Directive's security posture. Partner with Legal, Insurance, and Finance on privacy, data governance, and regulatory compliance.

Maintain documentation for security policies, controls, audits, and evidence collection. Build and/or manage company‑wide security awareness and phishing training programs. Educate employees on evolving cybersecurity threats, social engineering, AI usage and data protection best practices. 7+ years of experience in cybersecurity, information security or risk management. ~Demonstrated experience performing cybersecurity risk assessments and threat modeling. ~ Strong knowledge of cloud‑first and SaaS‑based environments including Google Workspace, Salesforce, NetSuite, Okta and modern identity platforms. ~ Experience implementing and maintaining security frameworks such as SOC 2, ISO 27001 or the NIST Cybersecurity Framework. ~ Experience working within fully remote organizations supporting distributed workforces. ~ Strong executive communication skills with the ability to translate technical risk into business impact. ~ CISSP, CISM, CRISC, or equivalent cybersecurity certification is strongly preferred.

Develop and execute a scalable cybersecurity roadmap that measurably improves Directive's overall security posture. Complete enterprise‑wide risk and threat assessments, resulting in prioritized remediation plans for critical vulnerabilities. Maintain successful SOC 2 compliance and establish audit readiness across all security controls and documentation.

Reduce organizational cybersecurity risk through stronger identity management, endpoint protection, and security governance.



Establish measurable security KPIs and provide regular executive reporting on risks, trends, and program maturity. The annual base salary range for this position based in Canada is $165,000–$200,000 CAD.

Medical, dental, vision plans, disability, and life insurance coverage for you and your family that fit your lifestyle, including a 100% employer‑paid plan for you and a 50% employer contribution for your dependents. Physical therapy through Omada, fertility support through Carrott, thousands of Aaptiv virtual workouts, complimentary One Medical membership for primary and virtual care.

Time Off: Unlimited PTO (2‑week minimum), Paid Company Holidays, Your Birthday Off, End of Year Recharge (Closed December 24 – January 1), Paid Parental Leave.

Bonus: Annual bonus based on tenure, which scales in total amount over time. As a remote‑first company, you’ll have the ability to work from anywhere in the US, with the option to enjoy our state‑of‑the‑art offices in Irvine, California. This role has the opportunity to operate 100% virtually from your home office.

We primarily collaborate with our colleagues through virtual meetings (Zoom), and Slack. In this role, you will be required to operate a laptop computer (PC or Mac available), computer software platforms, and other office productivity tools as necessary. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform essential job functions.

If you require reasonable accommodations in completing this application, interviewing, completing any pre‑employment testing, or otherwise participating in the employee selection process, direct your inquiries to [email protected]’re committed to fostering a more diverse and inclusive culture in the digital landscape. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. #

📌 Director of IT Security (Remote Canada) (Mississauga)
🏢 Directive
📍 Mississauga