Directive is hiring a Senior IT Manager (Remote US)

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 to streamline cost structures.
• Manage and mentor the IT Manager, while also 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), 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 that the IT Manager cannot resolve.
• 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.

Requirements

• 5+ years of experience in IT operations or systems administration.
• 3+ years of leadership experience with a willingness to remain hands-on in the trenches.
• Technical Versatility: You are comfortable pivoting from strategic planning to fixing a broken laptop or debugging a software error.
• Proven 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 a heavy reliance on cloud tools.
• Demonstrated experience architecting workflows between business systems (e.g., ERP to CRM integrations).
• Excellent communication skills with the ability to translate technical concepts into business value for executive leadership.

Nice to Have

• Previous experience leading or managing SOC 2 Type 2 and/or ISO 27001 audits is 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 with a passion for enabling employee success through technology.

Benefits

• 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)
• Access to certified therapists through Spring Health, membership to Headspace
• Physical therapy through Omada, thousands of Aaptiv virtual workouts, complimentary One Medical membership for primary and virtual care
• Unlimited PTO (2-week minimum), Paid Company Holidays, Your Birthday Off, End of Year Recharge (Closed December 24 - January 1), Paid Parental Leave
• Traditional and Roth 401(k) with a 3% company match
• Annual bonus based on tenure, which scales in total amount over time
• Annual Company-wide Retreat

Additional Information

• You’ll have the ability to work from your home office.
• For some positions, as posted, we will accommodate global opportunities where we have established businesses, including Canada, Mexico, and the UK.
• For global locations, you must have established and current work authorization and permanently reside in that country.
• You will be required to operate a laptop computer (PC or Mac available), computer software platforms, and other office productivity tools as necessary.
• Due to the nature of this role, you must be able to remain stationary for extended periods, must be able to observe and interpret written and/or verbal communication, must have reliable internet access, and a professional background.
• 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 recruiting@directiveconsulting.com.