Head of GTM Engineering

Workleap; Canada; Remote; CAD 125,000 - 150,000; Full time

Job summary

A forward-thinking company is seeking a Head of GTM Engineering to lead a dynamic team focused on building and optimizing an AI-powered go-to-market system. This role is perfect for those who thrive on innovation and are passionate about leveraging AI to drive growth and efficiency. You will be responsible for developing automated workflows, integrating key tools, and creating scalable growth playbooks that enhance revenue generation. Join a collaborative environment that values creativity and supports your professional development while making a significant impact on the company's success.

Qualifications

• Expertise in AI automation and data scraping with tools like BeautifulSoup and Scrapy.
• Proven leadership experience in fast-paced environments.

Responsibilities

• Design and implement AI-driven outbound automation workflows.
• Optimize and integrate the GTM tech stack to enhance efficiency.

Skills

AI Automation

Data Scraping

Python

SQL

API Integration

Team Leadership

Signal-Based Selling

Tools

HubSpot

Salesforce

Clay

Clearbit

ZoomInfo

Zapier

Make (Integromat)

Airops

dbt

Job description

Workleap builds practical employee experience software that makes work simpler.

Our products include Workleap, a simple employee experience platform to boost engagement, drive performance, and develop teams, and ShareGate by Workleap, a single, trusted out-of-the-box solution for fast and secure migration, adoption, and Copilot readiness—simplifying data management across Microsoft 365.

With over 20,000 happy customers in more than 100 countries, Workleap products are a must-have for businesses looking to create a more engaging and successful workplace.

Job Description

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. Reporting to the Director of Growth, you’ll lead a small team of GTM Engineers, working at the intersection of AI, automation, data, and growth to supercharge outbound, inbound, ABM, and paid marketing efforts.

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.

So, what will your new role look like?

• Build & Scale AI-Driven Outbound → Design a fully automated outbound & allbound system, integrating AI, intent data, and unstructured data sources.
• Develop Scalable Growth Playbooks → Create hyper-targeted market signals and playbooks that drive revenue.
• Power ABM & Paid Marketing → Implement AI workflows for account-based marketing (ABM) and optimize paid acquisition through better intent data.
• Integrate AI Agents & Automate GTM Workflows → Deploy AI-driven automation across sales, marketing, and growth teams.
• Optimize the GTM Tech Stack → Integrate key tools like Hubspot, Salesforce, Clay, Clearbit, ZoomInfo, and custom AI agents.
• Support Sales & Growth Teams → Build automated messaging and workflows that help sales teams close more deals, faster.

A typical week?

• Design, implement, and test AI-driven outbound automation workflows.
• Develop and refine multi-signal playbooks for outbound targeting and engagement.
• Optimize and integrate the GTM tech stack (HubSpot, Salesforce, Clay, Clearbit, ZoomInfo, etc.).
• Support sales and marketing teams by deploying automation to improve engagement efficiency.
• Run rapid AI-driven GTM experiments, track results, and continuously optimize.
• Work closely with growth, marketing, and sales teams to ensure AI automation delivers real business impact.

What does your future team look like?

The GTM Engineering team is a brand new team at Workleap, operating within the broader Growth function. Operating at the intersection of AI, automation, data, and growth, this team plays a critical role in optimizing and scaling our go-to-market strategy.

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—not just for GTM but across Workleap to enhance efficiency across multiple teams.

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.

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!

By applying to this job, you are confirming that you have read and agree to the terms of our privacy policy.

#LI-Remote

Apply for this job

* indicates a required field

First Name *

Last Name *

Email *

Phone *

Resume/CV *

Enter manually

Accepted file types: pdf, doc, docx, txt, rtf

Enter manually

Accepted file types: pdf, doc, docx, txt, rtf

Website

LinkedIn Profile

What is your preferred language? * Select...

How did you first hear about Workleap? * Select...

If you mentioned ‘Other’ Please put the reason here:

Are you legally authorized to work in Canada? * Select...