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

So, what will your new role look like?

We're looking for a Head of GTM Engineering to build, scale, and optimize an AI-powered GTM system that drives pipeline, revenue, and efficiency. You'll lead a small team of GTM Engineers, working at the intersection of AI, automation, data, and growth to supercharge outbound, inbound/SEO, paid, and community motions.

If you're a hacker at heart, obsessed with AI automation, and thrive on creative technical solutions that unlock revenue, this role is for you.

Responsibilities:

• Build & Scale AI-Driven GTM Systems Design an automated outbound & allbound engine that fuses AI agents, multi-signal intent, and unstructured data; ship scrappy, high-impact playbooks fast.

• Create Repeatable Growth Playbooks Turn market/buyer signals into precision workflows for outbound, inbound/SEO, paid, and community that reliably move pipeline and ARR.

• Stand Up the AI Foundation & Legacy Build internal know-how: patterns, docs, enablement, and guardrails for using AI across GTM; drive thought leadership inside Workleap on where AI creates leverage.

• Integrate AI Agents & Automate Workflows Deploy agentic automations across sales, marketing, and growth; connect MCPs/APIs to orchestrate research, enrichment, routing, scoring, and messaging.

• Optimize the GTM Data & Tooling Stack Own (with RevOps) integrations and data flows across HubSpot, Salesforce, Snowflake, Clay, Clearbit, ZoomInfo, Common Room, Bright Data, Cursor, Make/Zapier, AirOps, and custom services.

• Build SEO & Paid Content Ops Prototypes Ship programmatic SEO tools (e.g., Bright Data pipelines, entity libraries, internal content generators) that accelerate acquisition and learning loops.

• Support Sales & Growth Teams Deliver automated messaging, enablement tools, and workflows that increase speed-to-engage and win rates.

• Measure What Matters Instrument experiments, scoring models, and playbooks end-to-end; set clear success metrics and iterate quickly.

A typical week?

• Design, implement, and test AI-driven automation workflows for outbound and allbound.

• Develop and refine multi-signal playbooks for targeting, scoring, routing, and engagement.

• Build/extend data pipelines in Snowflake and dbt; wire Cursor/MCPs into GTM tools via APIs.

• Prototype SEO tools and programmatic content workflows using Bright Data and internal services.

• Optimize and integrate the GTM stack (HubSpot, Salesforce, Clay, Clearbit, ZoomInfo, Common Room, Cursor, Make/Zapier, AirOps).

• Partner with sales, marketing, and growth to deploy automations that improve engagement efficiency.

• Run rapid AI-driven GTM experiments, track results, and continuously optimize.

What does your future team look like?

The GTM Engineering team is a brand-new team at Workleap within the broader Growth function. Operating at the intersection of AI, automation, data, and growth, the team is responsible for the systems, agents, and playbooks that scale our go-to-market. You'll lead two GTM Engineers to start, with room to grow.

What are the next challenges awaiting your team?

• Build and scale a fully automated outbound and allbound GTM system—a foundational growth engine for Workleap.

• Expand the GTM Engineering team to tackle more automation and AI use cases.

• Operationalize AI-driven workflows at scale across Workleap to enhance efficiency across multiple teams.

• Establish Workleap's internal AI playbook and enablement library so every GTM function benefits from AI leverage.

Qualifications

• AI Automation & Data Scraping Expertise You're a master at scraping, extracting, and operationalizing data at scale.
  • Expertise in data scraping (BeautifulSoup, Scrapy, Puppeteer) and enrichment pipelines using tools like Clay, Clearbit, Apollo, ZoomInfo.
  • Building AI-driven lead scoring models to prioritize high-propensity accounts.
• Team Leadership & People Management You have experience leading and scaling a team and driving execution in a fast-paced environment.
• Technical GTM Skillset Strong Python, SQL, and API experience to build and scale GTM workflows.
  • Ability to design, build, and optimize automated GTM workflows using tools like Zapier, Make (Integromat), Airops, dbt, and custom scripts.
• GTM SaaS Experience You've built data-driven playbooks, outbound systems, and ABM strategies that drove revenue.
• Intent Data Utilization & Signal-Based Selling
  • Experience in aggregating and acting on buyer intent signals (e.g.,ZoomInfo, Clay, website visitor tracking, LinkedIn engagement).
  • Building custom enrichment workflows to combine firmographics, technographics, and behavioral signals into actionable intelligence.
• Deep Curiosity & Creativity You love finding hidden growth levers and automating what others think is manual.
• Ownership & Execution You don't wait. You build, test, and launch—fast.

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

We are looking forward to getting to know you!

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