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[Hiring] Director of Marketing at Workleap

February 25, 2026

Job Overview

  • Date Posted
    February 25, 2026
  • Location
  • Expiration date
    --
  • Gender
    Both
  • hiringOrganization

    Workleap

Job Description

Job Description 

The Mission: To architect the “People Management Agent”

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

We are looking for a leader who sees a $29M business as a solid foundation and wants to build the marketing engine capable of transforming a portfolio of high-performing products into a dominant platform. As Marketing Director, you will shape the category narrative and drive the overall demand generation engine that will propel 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 our revenue objectives.

  • Defining the category: Transforming the vision of the “People Management Agent” into a dominant market positioning and ensuring a strong resonance with modern leaders.
  • Optimize the growth engine: Evaluate our current demand generation strategies and evolve them into a scalable machine augmented by AI.
  • Leveraging the Context Engine: Capitalizing on our unique positioning around Employee Context to differentiate ourselves in a competitive HR-tech market.
  • Adopt a revenue-oriented approach: Run the marketing function with a P&L mentality by prioritizing CAC, LTV and pipeline velocity rather than vanity metrics.
  • Execute the global GTM strategy: Identify opportunities in new segments and geographic markets and build playbooks to replicate our success internationally.
  • Structuring and developing the team: Developing a creative, high-performing and rigorously data-driven marketing team.

The Challenge: Building a Marketing System.

Going from $29M to $100M ARR requires a shift in mindset: moving from “doing marketing” to “building a marketing system.” Your main 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 this 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; vision of technology as a performance multiplier.
  • Strategic storyteller: Ability to transform a complex technical vision into a clear, essential, and human narrative; preference for clarity and candor over corporate jargon.
  • Revenue-oriented: Mastery of sales and finance jargon; obsession with pipeline contribution and efficiency.
  • Collaborative and direct: Valuing transparency and honest debate; comfortable in an environment where strengths and areas for improvement are openly discussed.


Why Workleap?

Simple conviction: work can be better, and creating the tools to prove it. High-performance leadership environment, low ego, and the ambition to build a generational Canadian tech company. Autonomy for 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: to make work simpler—and better—for everyone. Challenges fuel our creativity, we thrive on intensity, and pushing boundaries is part of our DNA. We believe the best ideas are born from experimentation, continuous learning, and sometimes even discomfort—that’s how we grow.

Since 2006, we’ve been reinventing the way teams work, combining creativity and technology to solve real IT and HR problems. We move fast, we learn constantly, and we always keep our clients at the heart of our decisions. If you’re proactive, take charge, love collaborating, and aren’t afraid to dive into the unknown—you’ll fit right in with us.

Additional information

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

Our goal is to build a healthy and inclusive work environment. This is everyone’s responsibility. 

Our Candidate Experience Process at Workleap:
Phone interview – Virtual interview via Teams – Situational exercise – Job offer

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

We can’t wait to get to know you!

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