Associate Creative Director, Copy – Remote in Winnipeg

Directive is a revenue-first marketing consultancy built to serve B2B SaaS, enterprise technology, industrial, and commerce brands. We are looking for an Associate Creative Director who will translate Moments that Matter into creative territories, messaging hypotheses, campaign concepts, headlines, CTAs, and copy direction that designers can execute against. The Associate Creative Director will bring senior-level creative judgment to work that is fast-moving, digital-first, and tied directly to business outcomes.

This person will help shape the ask, identify stronger creative angles, and translate strategic inputs into assets that feel clear, compelling, and differentiated. They will represent creative in strategic new-business and portfolio-sales opportunities, help build speculative and portfolio creative, and support Directive’s move toward campaign-style case studies that can drive account growth and new revenue.

This is an individual contributor role — no direct reports — but the work will be high-visibility and the standard will be high. The ideal candidate is copywriting-led and campaign-minded. They should have enough executive presence to participate in client and leadership conversations, but remain hands-on enough to write copy, review briefs, develop messaging territories, and shape creative direction without needing a fully staffed creative team around them.

Success means helping Directive replace deliverable-based requests with campaign briefs grounded in business objectives, buyer insight, test variables, and success metrics. The ACD should raise the quality of creative thinking before work reaches production, improve how Directive communicates to technical and enterprise buyers, and create the foundation for a scalable performance creative practice.

WILL OWN

• Campaign Strategy: The ACD owns the idea, message, and creative direction before production begins.
• Support new-business and portfolio-sales opportunities with speculative creative, campaign narratives, and stronger creative presence in strategic pitches.
• Create the foundation for Directive’s strategic creative approach.
• Primary responsibility is creative direction, campaign concepting, messaging strategy, and performance copy direction.
• Turns campaign and creative briefs into territories, concepts, hooks, headlines, CTAs, landing-page narrative direction, and message sequencing.
• Partners with designers by giving them a strong concept and copy direction to execute against.
• Builds the early proof points, examples, and campaign-style case studies needed to support future creative revenue growth.

WHAT SUCCESS LOOKS LIKE

• 30-day success signal: Internal teams understand why this role exists, what it owns, and how creative requests should start shifting from asset asks to campaign briefs.
• Audited current creative requests, briefs, production workflows, pitch materials, and performance creative examples.
• Met with Creative Production, Paid Media, Growth, Sales, Account leadership, and executive stakeholders to understand opportunities.
• Defined what a “good” campaign brief needs to include before work enters production.
• Created a first draft of the campaign creative brief template tied to Moments that Matter / Stratos.
• Identified 2–3 priority use cases where the new model can prove value quickly.
• Produced at least one example of a stronger campaign territory or messaging direction from existing work.

• 90-day success signal: Directive can point to live examples where creative strategy made the work sharper before production began.
• Run several real briefs through a campaign-level creative process.
• Developed creative territories, messaging angles, campaign copy, and testing recommendations for priority initiatives.
• Supported at least one new-business, strategic account, or portfolio-sales opportunity with speculative or campaign-style creative.
• Built a working partnership model with production designers.
• Created early examples of campaign-style case studies or internal proof points.
• Established a lightweight creative review rhythm focused on concept quality, message clarity, testability, and business relevance.
• Begun defining the message/proof library and taxonomy needed for learning to compound across campaigns.

QUALIFICATIONS

• 4–6 years of professional creative experience, with a meaningful portion in an agency, professional services, or B2B marketing environment.
• A portfolio that shows range across brand work and performance creative.
• Experience developing campaigns from concept through execution.
• Ability to maintain and evolve brand standards across multiple channels.
• Understanding of creative strategy and storytelling.
• Ability to translate insights into creative hypotheses and campaign concepts.
• Executive presence and confidence presenting creative strategy.
• Strong understanding of performance creative, testing methodology, message iteration, and revenue-oriented creative measurement.
• Ability to partner effectively with production designers, paid media strategists, and other stakeholders.
• Comfort operating in ambiguity and helping shape the brief when the request is not fully formed.

Technical and Industry Knowledge

• Digital marketing and social media.
• UX/UI design.
• Video and motion graphics.
• Content strategy.
• Creative software such as Adobe Creative Cloud.
• Tools — Required: Adobe Creative Suite, Adobe After Effects and Premiere Pro, Figma.
• Familiarity with A/B testing and CRO tools.

WHAT WE OFFER

• The annual base salary range for this position based in Canada is $115,000-$125,000 CAD.
• Medical, dental, vision plans, disability, and life insurance coverage.
• Mental health support, physical therapy, and wellness programs.
• Unlimited PTO, 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.

WORK ENVIRONMENT

Directive is a remote-first company. This role operates 100% virtually from your home office. You will need a reliable setup, high-speed internet, and a professional working environment capable of running Adobe Creative Suite and video production software without interruption.

ADDITIONAL INFORMATION

At Directive, one of our core values is People First. We are committed to fostering a 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.