Senior IT Manager

Join to apply for the Senior IT Manager (Remote Canada) role at Directive. Directive Consulting is the leading B2B performance marketing agency that delivers real revenue—not just leads. We use Customer Generation, a marketing methodology developed by us, to cut through the noise. We drive pipeline, fuel SQLs, and scale brands serious about growth across paid media, SEO, CRO, RevOps, and go‑to‑market strategy. We move fast, think boldly, and hire people who challenge the status quo. If you love solving hard problems and want your work to mean something, you’ll fit right in. About the Role This position reports to the chief financial officer and is a crucial part of the infrastructure of both Directive and Abe. The Senior IT Manager oversees technology strategy, security compliance, and the IT budget. You will manage an IT Manager while also acting as a “Player‑Coach” who handles high‑level technical escalations, administers business systems, and supports the help desk during peak volume. Roles & Responsibilities Own the IT budget and partner with the CFO to identify cost‑saving opportunities. Conduct regular audits of the SaaS ecosystem to consolidate tools, manage renewals, and negotiate vendor contracts. Manage and mentor the IT Manager, while serving as a backup for daily operations during peak times or absence. Design and maintain an IT roadmap that supports business scalability without linear cost increases. Act as the primary system administrator for core business tools (NetSuite, Salesforce, Asana, PandaDoc, Notion, etc.), handling complex configurations and integrations. Ensure seamless data flow between Sales, Finance, and Operations by building and maintaining automations and API connections. Evaluate and implement new tools, taking ownership of technical setup, deployment, and training. Lead the execution of compliance frameworks (SOC 2), including gathering evidence and managing audit requirements. Respond to customer and vendor security questionnaires to accelerate sales cycles. Configure and enforce data governance policies across distributed tools (Notion, Drive, Stratos) to prevent data silos. Manage device security policies hands‑on using MDM software (Kandji) to protect company assets. Serve as the final escalation point for technical issues that the IT Manager cannot resolve. Partner with the IT Manager to manage the helpdesk queue and resolve tickets to maintain SLAs. Develop and execute disaster planning, data backup strategies, and business continuity protocols. Maintain high‑level documentation, SOPs, and internal knowledge bases for system architecture. What You’ll Bring 5+ years of experience in IT operations or systems administration. 3+ years of leadership experience with a willingness to remain hands‑on. Technical versatility and comfort pivoting from strategic planning to troubleshooting. Experience administering a complex SaaS‑based environment (Google Workspace, Salesforce, NetSuite, Asana, etc.). Strong financial acumen with experience managing budgets and vendor negotiations. Experience working in a remote‑first workforce with heavy reliance on cloud tools. Demonstrated experience architecting workflows between business systems (e.g., ERP to CRM integrations). Excellent communication skills and the ability to translate technical concepts into business value for executive leadership. What You Offer Previous experience leading or managing SOC 2 Type 2 and/or ISO 27001 audits (highly preferable). Deep expertise in macOS environments and modern MDM tools (Kandji/Jamf). Relevant professional certifications (e.g., Cloud Architecture, Security, or IT Management). Strong analytical, diagnostic, and problem‑solving skills. A personable, professional demeanor passionate about enabling employee success through technology. What We Offer Compensation for this role includes a competitive base salary. Medical, dental, vision, disability, and life insurance coverage for you and your family. Benefits to support the whole person: mental health access via Spring Health and Headspace, physical therapy through Omada, virtual workouts, One Medical membership, unlimited PTO (2‑week minimum), paid company holidays, your birthday off, end‑of‑year recharge, paid parental leave. Financial benefits: 401(k) with 3% company match. Annual bonus based on tenure and a company‑wide retreat. Health plans: 100% employer‑paid plan for you, 50% employer contribution for dependents (US, CAD, MX). Work Environment Requirements As a remote‑first company, you will work from a home office. The role is 100% virtual, collaborating through Zoom and Slack. You must have reliable internet access, a professional background, and the ability to remain stationary for extended periods while operating a laptop (PC or Mac). Global opportunities exist in Canada, Mexico, and the UK; applicants must have current work authorization and reside in the country. Additional Information At Directive, one of our core values is People First. We’re committed to fostering a diverse and inclusive culture. All qualified applicants will receive consideration for employment under the EEO policy. Reasonable accommodations may be made for qualified individuals with disabilities. If you require accommodations during the application or interview process, please contact recruiting@directiveconsulting.com. Referrals increase your chances of interviewing at Directive by 2×. #J-18808-Ljbffr