Directive is hiring a Senior IT Manager (Remote US)

Directive Consulting is looking for a Senior IT Manager to lead our technology strategy, security compliance, and IT budget. In this remote US role, you will act as a Player-Coach, overseeing high-level technical escalations while directly administering business systems and supporting the helpdesk.

What You'll Do

• Act as primary System Administrator for core business tools like NetSuite, Salesforce, Asana, PandaDoc, and Notion, 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 execution of compliance frameworks like 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 to prevent data silos.
• Manage device security policies hands-on using MDM software like Kandji.
• Serve as final escalation point for technical issues, troubleshooting complex hardware and software problems.
• Partner with the IT Manager to manage the helpdesk queue, jumping in to resolve tickets and support employees 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.

What We're Looking For

• 5+ years of experience in IT operations or systems administration.
• 2+ years of leadership experience with a willingness to remain hands-on.
• Deep expertise in remote-first, macOS environments and modern MDM tools like Kandji or Jamf.
• Proven experience administering a complex SaaS-based environment (Google Workspace, Salesforce, NetSuite, Asana, etc.).
• Technical versatility: 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.

Nice to Have

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

Technical Stack

• NetSuite, Salesforce, Asana, PandaDoc, Notion, Google Workspace, Kandji/Jamf

Team & Environment

You will join a small, nimble environment and manage an IT Manager who handles day-to-day logistics. This role reports to the Head of Finance.

Benefits & Compensation

• Competitive base salary and annual bonus based on tenure.
• Medical, dental, vision plans, disability, and life insurance coverage for you and your family.
• 100% employer-paid plan for you and 50% employer contribution for your dependents (US, CAD, MX).
• Mental health access to certified therapists through Spring Health, membership to Headspace.
• Physical health benefits: Physical therapy through Omada, thousands of Aaptiv virtual workouts, complimentary One Medical membership.
• 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 Company-wide Retreat.

Work Mode

This is a remote position open to candidates in the US, Canada, Mexico, and the UK.

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.