Marketing Director, Workleap Platform

About Workleap

Workleap is a tech company based in Montreal, dedicated to making work simpler. Since 2006, we've been building innovative products that help HR and IT teams overcome their biggest challenges.

Workleap offers two distinct product lines:

• The Workleap platform, an AI-powered HR solution that enhances team performance and boosts employee engagement.
• ShareGate, the undisputed leader in Microsoft 365 migration and governance, recognized by IT professionals worldwide for its simplicity.

Today, over 20,000 companies globally rely on Workleap products to grow, evolve, and operate.

We are builders at heart, passionate about one clear goal: creating the simplest products that deliver exceptional value to our customers, period.

About the Role: Marketing Director, Workleap Platform

The Mission: Architect the "People Management Agent"

Workleap Platform is at a pivotal moment in its growth trajectory. With a solid foundation of $29M ARR, we have completed a phase of rapid expansion and M&A. Today, our focus is clear: unify, refine, and scale. We are evolving from a suite of powerful tools into a cohesive People Management Agent, powered by an Employee Context Engine that helps managers lead with greater clarity and less friction. This is not a management role; it's a builder's opportunity.

We are seeking a leader who sees a $29M business as a solid foundation and wants to design the marketing engine capable of transforming a portfolio of performing products into a dominant platform. As the Marketing Director, Workleap Platform, you will shape the category narrative and drive the global demand generation engine that will lead us to $100M ARR.

The Mandate: Strategy, Storytelling, and Revenue

Reporting directly to the Chief Revenue Officer (CRO), you will act as the strategic marketing leader for the Platform business unit, ensuring strong alignment between our brand promise and revenue objectives.

• Define the category: Transform the "People Management Agent" vision into a dominant market positioning and ensure strong resonance with modern leaders.
• Optimize the growth engine: Evaluate our current demand generation strategies and evolve them into a scalable, AI-augmented machine.
• Leverage the Context Engine: Capitalize on our unique positioning around Employee Context to differentiate ourselves in a competitive HR-tech market.
• Adopt a revenue-oriented approach: Drive the marketing function with a P&L mindset, prioritizing CAC, LTV, and pipeline velocity over vanity metrics.
• Execute global GTM strategy: Identify opportunities in new segments and geographic markets and build playbooks to replicate our success internationally.
• Structure and evolve the team: Develop a creative, high-performing, and rigorously data-driven marketing team.

The Challenge: Building a Marketing System

Scaling from $29M to $100M ARR requires a shift in approach: moving from "doing marketing" to "building a marketing system." Your primary challenge will be to structure more mature and unified marketing operations while preserving the agility that has driven our success. You will need to identify where our processes require more rigor, instill that discipline, and support the team in this professionalization.

Qualifications

• Scale-up Veteran: 8+ years of experience in B2B SaaS marketing; ideally a trajectory in a growth phase between $10M and $50M ARR.
• AI-Forward Thinker: Advanced use of AI tools to automate workflows, optimize investments, and personalize the customer journey; a vision of technology as a performance multiplier.
• Strategic Storyteller: Ability to transform complex technical vision into clear, essential, and human narratives; a preference for clarity and frankness over corporate jargon.
• Revenue-Oriented: Mastery of sales and finance language; obsession with pipeline contribution and efficiency.
• Collaborative and Direct: Values transparency and honest debates; comfortable in an environment where strengths and areas for improvement are openly discussed.

Why Workleap?

Our simple conviction: work can be better, and we create tools to prove it. We offer a leadership environment focused on high performance, low ego, and the ambition to build a generational Canadian tech company. Enjoy the autonomy of a founding marketing leader within a $29M business unit, supported by the stability and reach of the Workleap ecosystem ($100M+).

Who We Are

We are a team of curious and passionate creators, united by the same goal: making work simpler – and better – for everyone. Challenges fuel our creativity, intensity drives us, and pushing boundaries is part of our DNA. We believe the best ideas come from experimentation, continuous learning, and sometimes even discomfort—that's how we evolve.

Since 2006, we've been reinventing how teams work, combining creativity and technology to solve real problems in IT and HR. We move fast, learn constantly, and always keep our clients at the heart of our decisions. If you are proactive, take initiative, love to collaborate, and aren't afraid to dive into the unknown – you will fit right in with us.

Additional Information

At Workleap, we build together, trust each other, and support each other, in success or failure. You can express yourself, grow, and develop your creativity in an environment that adapts to your daily life and needs.

Our aspirations are to build a healthy and inclusive work environment. This is everyone's business.

Our Workleap Candidate Experience Process:

• Phone Interview
• Virtual Teams Interview
• Situational Exercise
• Job Offer

As a technology company, we use AI to optimize recruitment, while ensuring that all evaluation decisions remain human.

We look forward to getting to know you!

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Key skills/competency

• Marketing Strategy
• Demand Generation
• B2B SaaS
• AI-powered Marketing
• Product Positioning
• Revenue Growth
• Go-to-Market (GTM)
• Leadership
• P&L Management
• Data-driven Marketing