Senior IT Manager; Remote

About The Role

Directive Consulting is the performance marketing agency for SaaS and Tech companies. We use Customer Generation (a marketing methodology developed by us) which focuses on SQLs and Customers instead of traditional metrics like MQLs. We offer Paid Media, SEO, Performance Creative, and Video to our clients by creating comprehensive digital marketing strategies that allow our clients to hit their SQL targets, every time.

This role reports to the Head of Finance and is a crucial part of the team and the infrastructure of both of our agencies, Directive and Abe. The Senior IT Manager is responsible for overseeing our technology strategy, security compliance, and IT budget.

In this role, you will manage an IT Manager who handles day-to-day logistics, but you will also be a "Player-Coach" who is not afraid to roll up your sleeves. You will handle high-level technical escalations, directly administer our business systems, and step in to support the helpdesk when volume is high. We are a small, nimble environment, and we need a leader who can strategize with the Head of Finance one hour and troubleshoot a complex integration issue the next.

• Act as the primary System Administrator for core business tools (Net Suite, Salesforce, Asana, Panda Doc, Notion, etc.), personally 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 the technical setup, deployment, and training for the organization.

• Lead the execution of compliance frameworks (SOC
  2), including gathering evidence and managing audit requirements.

• Directly 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, troubleshooting complex hardware/software problems.

• Partner with the IT Manager to manage the helpdesk queue, jumping in to resolve tickets and support employees directly 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.

• Own the IT budget and partner with the Finance team to identify cost-saving opportunities.

• Conduct regular audits of the SaaS ecosystem to consolidate tools, manage renewals, and negotiate vendor contracts to streamline cost structures.

• 5+ years of experience in IT operations or systems administration.

• 2+ years of leadership experience with a willingness to remain hands-on in the trenches.

• Deep expertise in remote-first, macOS environments and modern MDM tools (Kandji/Jamf).

• Proven experience administering a complex SaaS-based environment (Google Workspace, Salesforce, Net Suite, Asana, etc.).

• Technical Versatility:
  You are comfortable pivoting from strategic planning to fixing a broken laptop or debugging a software error.

• Strong financial acumen with experience managing budgets and vendor negotiations.

• Excellent communication skills with the ability to translate technical concepts into business value for executive leadership.

• Previous experience leading or managing SOC 2 Type 2 and/or ISO 27001 audits is highly preferable.

Compensation for this role includes a competitive base salary

• 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 (US, CAD, MX)

• Benefits to Support the Whole Person:

  • Mental - Access to certified therapists through Spring Health
    , membership to Headspace

  • Physical - Physical therapy through Omada, thousands of Aaptiv virtual workouts, complimentary One Medical mem…