Head of Marketing - Workleap Platform

Company Description

Workleap is a Montreal-based tech company on a mission to make work simpler.

Since 2006, we’ve been building game-changing products that tackle HR and IT’s biggest challenges.

Workleap operates two distinct product lines:

• The Workleap Platform, an AI-powered HR solution designed to drive team performance and boost employee engagement.

• ShareGate, the leading Microsoft 365 migration and governance solution, trusted by IT professionals worldwide for its unmatched simplicity.

Today, more than 20,000 companies rely on Workleap products to grow, lead, and operate with confidence.

We’re builders at heart, with a clear purpose: to craft the simplest products that deliver exceptional value for our customers. Period.

Job Description

The Mission: Architecting the "People Management Agent"

Workleap Platform is at a pivotal moment in its growth journey. With a solid $29M ARR foundation, we’ve successfully navigated rapid expansion and M&A. Now, our focus shifts to unification, refinement, and scale. We are evolving from a suite of successful tools into a cohesive People Management Agent, powered by an Employee Context Engine that helps managers lead with more clarity and less friction. This is not a caretaker role. It’s a builder opportunity.

We’re looking for a leader who sees a $29M business with strong bones and wants to design the marketing engine that transforms a successful product portfolio into a dominant platform. As Director of Marketing, you will shape the category narrative and own the global demand engine that propels us toward $100M ARR.

The Mandate: Strategy, Storytelling, and Revenue

Reporting directly to the Chief Revenue Officer (CRO), you will serve as the strategic marketing leader for the Platform business unit, ensuring our brand promise and revenue targets are perfectly aligned.

• Define the Category: Take the "People Management Agent" vision and turn it into a dominant market position. You’ll ensure our messaging resonates with modern leaders who need real-time context to manage effectively.

• Optimise the Growth Engine: You will evaluate our current demand-gen motions and lead the transition to a scalable, AI-augmented machine. You'll focus on high-velocity lead-to-revenue conversion across both PLG and Sales-led paths.

• Leverage the Context Engine: Use our unique positioning around "Employee Context" to create programmes that differentiate us in a crowded HR-tech market.

• Revenue-First Partnership: Working closely with the CRO, you will bring a P&L mindset to the marketing function—prioritising CAC, LTV, and pipeline velocity over vanity metrics.

• Global GTM Execution: Identify "white space" in new segments and geographies. You’ll build the playbooks that allow us to replicate our North American success on a global scale.

• Coach and Scale: You will lead and elevate a team of marketing specialists, fostering a culture that is both highly creative and ruthlessly data-driven.

The Challenge: Building a marketing system

The journey from $29M to $100M requires a shift from "doing marketing" to "building a marketing system." Your primary challenge will be maturing our operations and unifying our narrative while maintaining the agility that got us here. You’ll need to be comfortable identifying where our current processes need more rigour and leading the team through that professionalisation.

Qualifications

• The Scale-Up Veteran: 8+ years in B2B SaaS marketing, ideally having navigated the $10M–$50M ARR growth phase.

• The AI-Forward Thinker: You are already using AI tools to automate workflows, optimise spend, and personalise the customer journey. You view technology as a force multiplier for your team.

• The Strategic Storyteller: You can take a complex technical vision and make it feel essential and human. You value directness and clarity over corporate jargon.

• Revenue-Centric: You speak the language of sales and finance. You are obsessed with pipeline contribution and efficiency.

• Collaborative & Direct: You value transparency and honest debate. You want to work in an environment where we talk openly about what’s working and what we need to improve.

Why Workleap?

We believe work should be better, and we’re building the tools to prove it. You’ll join a leadership team that values high performance, low ego, and the ambition to build a generational Canadian tech company. You will have the autonomy of a founding marketing leader within a $29M business unit, supported by the stability and reach of the broader $100M+ Workleap ecosystem.

Who we are

We’re a team of curious minds and bold builders, brought together by a shared drive to make work simpler - and better - for everyone. Challenges fuel our creativity, fast-paced environments keep us sharp, and pushing boundaries is just part of how we operate. We believe the best ideas come from experimentation, rapid learning, and even the occasional discomfort - that’s where growth happens.

Since 2006, we’ve been rethinking the way teams work, blending creativity and tech to solve real problems in IT and HR. We move quickly, we learn constantly, and we always keep our customers at the center of what we do. If you're a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to leap into the unknown - you’ll fit right in.

Additional Information

At Workleap, we build together, we trust each other, and we support each other in success or failure. You will be able to express yourself, evolve and develop your creativity in an environment that will adapt to your daily life and your needs.

We strive to create a healthy and inclusive work environment. This is everyone’s business.

Our Candidate Experience Flow at Workleap:
Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer

As a tech-forward company, we leverage AI tools to enhance our recruitment process, while ensuring all hiring decisions remain human-led.

We are looking forward to getting to know you!

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