Job Description

About Directive Consulting

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 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.

Roles & Responsibilities

Hands-On Systems Administration & Integration: 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 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.
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.
Own the IT budget and partner with the Finance team to identify cost-saving opportunities.

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).
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

Competitive base salary
Medical, dental, vision plans, disability, and life insurance coverage for you and your family.
Unlimited PTO (2-week minimum), Paid Company Holidays, Your Birthday Off, End of Year Recharge, 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.

Work Environment Requirements

This role has the opportunity to operate 100% virtually from your home office. For some positions, we will accommodate global opportunities where we have established businesses, including Canada, Mexico, and the UK.

If you require reasonable accommodations in completing this application, interviewing, or participating in the employee selection process, direct your inquiries to [email protected] .

Diversity & Inclusion

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.

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Senior IT Manager (Remote Canada)