Location: Flexible within Canada (Toronto HQ, EST focus)
Type: Full-Time | Hybrid/Flexible | Leadership Role
Compensation: $90,000 - $110,000

Lead the Next Chapter of Digital Growth

Flywheel makes digital meaningful. We don’t just support digital and AI-enabled transformation, we architect it for ambitious B2B organizations. We help clients turn complex goals into measurable results by blending strategic thinking with integrated expertise in design, technology, and content. Now, we’re hiring our first Director of Marketing; a pivotal leadership role for someone ready to establish and scale a modern marketing function.

This is a rare opportunity for an experienced B2B marketer who wants to step into a builder role - someone who’s mastered the mechanics of demand generation and reputation building and is eager to shape marketing for a thriving digital agency. Flywheel has adapted through decades of technological change with a team that values curiosity, diverse expertise, and a focus on innovation to drive authentic outcomes. If you're motivated by meaningful challenges and collaborative growth, we should talk about what joining Flywheel could look like for you.

Why This Role Stands Out

• High Autonomy & Impact: You'll have the space and trust to define strategy, implement programs, and build out a team.
• B2B Focus, Purpose-Driven Clients: Our clients are mid-market to enterprise B2B companies who come to us with a purpose. They're not looking for surface-level solutions, they want meaningful advancement. You’ll help us reach more of them.
• Integrated Digital Services: From custom web development and UX design to CRM and Salesforce integration to AI integration, Flywheel offers an unusually broad suite of services. That means more storytelling angles, more value propositions, and more marketing complexity to sink your teeth into.
• Leadership Access & Collaboration: You’ll work closely with leadership across business development and delivery. Your insights and execution will shape our growth trajectory.

Your Core Responsibilities

• Develop the Marketing Strategy: Shape our go-to-market plans. Listen to existing and potential clients, understand the market, and collaborate with leadership to define the marketing strategy and develop the marketing plans.
• Drive Awareness & Demand: Build brand and benefit awareness with the people and companies we can help most, instigating new relationships. Measurements include: Qualified Leads and engagement touchpoints.
• PR & Media Relations: Cultivate relationships with media and influencers to amplify Flywheel’s reputation, strengthen industry presence, and attract potential clients. Measurements include: Impressions and mentions, SEO authority.
• Messaging & Content Production: Create and share meaningful content that engages potential and existing clients, keeps Flywheel top of mind, and reinforces our positioning across industries. Measurements include: Impressions and conversions.
• Event Strategy & Execution: Evaluate the landscape of industry and partner events—deciding when (or if) to participate, sponsor, or organize Flywheel-hosted experiences. Develop a strategic approach to event presence that aligns with our brand, builds relationships, and maximizes ROI. Measurements include: Qualified leads.
• Execute Across Channels: Collaborate with internal and external resources to drive execution, test, and learn to find approaches that work best. Measurements include: Campaign ROI and qualified leads per campaign.
• Leverage data to understand results: See results and gain understanding. The Flywheel team is committed to show accountability and build momentum over time. With the support of the Flywheel team, define KPIs, track performance, and adapt plans.
• Voice of the Market: Stay close to our clients, partners, prospects, and industry to understand perspective, keep our message sharp, and our offers aligned.

What We're Looking For

• 6+ years of experience in B2B marketing.
• A naturally energizing presence: you welcome people with openness and authentic approachability, paired with the initiative to spark momentum.
• Demonstrated success building visibility and pipeline through earned and owned media.
• Comfort with tech-forward services: you’re fluent in the language of platforms, integrations, and digital experiences.
• Strong communication and leadership skills: you can articulate vision, produce collateral, collaborate across teams, and inspire trust.
• Analytical skills to critically interpret data to drive sound business decisions.

Bonus Points For

• Familiarity with AI Integration, Salesforce, Pardot, Content Management, and other CRM/marketing automation tools.
• Bilingualism (English & French).
• Experience marketing to business and technical audiences in sectors like finance, manufacturing, industrial supply, professional associations, or health.

What We Offer

• Influence & Ownership: Be the voice and architect of our marketing function.
• Flexibility: Work from wherever you work best. Most of our team operates in EST.
• Health & Dental Benefits: Comprehensive coverage from day one.
• Leadership Exposure: Work directly with business leaders across North America.
• Driven, non-hierarchical team: We enable each other to find success on one’s own terms.
• Growth Trajectory: Build a team, a strategy, and a legacy as Flywheel scales.