Senior IT Manager (Remote Canada)

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. Forget MQLs—we’re here to drive pipeline, fuel SQLs, and scale brands that are serious about growth. From Paid Media and SEO to CRO, RevOps, and Go-To-Market Strategy, we build marketing engines that win in SaaS and across B2B industries.

We move fast. We think boldly. We are elite. We hire people who challenge the status quo and push campaigns past what’s expected - sparking demand for bold, innovative brands. If you live for performance, love solving hard problems, and want your work to actually mean something, you’ll fit right in.

But here’s the fun part—we don’t just deliver results; we’re shaping the future of marketing. Ready to build something that breaks the mold?

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.

Roles & Responsibilities:

Hands-On Systems Administration & Integration:

• 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.

Security, Compliance & Governance:

• 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.

Operational Execution & Support:

• 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.

What You’ll Bring:

• 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, NetSuite, 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.

What We Offer:

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 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

• 💰 Financial - Traditional and Roth 401(k) with a 3% company match

• 🌟 Bonus - Annual bonus based on tenure, which scales in total amount over time

• 🌴 Annual Company-wide Retreat

Work Environment Requirements

As a remote-first company, 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.

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. 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.

To perform this job successfully, an individual must be able to perform each essential job duty satisfactorily. 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].

Additional Information

At Directive, one of our core values is People First. We’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. #LI-DC1