Opportunity at
WorkleapGTM Engineering - ShareGate
Workleap, a tech enterprise established in 2006 with operations in Montreal, seeks a GTM Architect, Expansion & Retention for its ShareGate product line. The organization creates…
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About This Role
Workleap, a tech enterprise established in 2006 with operations in Montreal, seeks a GTM Architect, Expansion & Retention for its ShareGate product line. The organization creates software relied upon by over 15,000 businesses globally, including Microsoft 365 migration tools and management solutions, alongside the Workleap Agent platform. This embedded engineering position operates within the go-to-market organization rather than back-office operations. The professional in this role will design, construct, and deploy…
Job Description
Workleap, a tech enterprise established in 2006 with operations in Montreal, seeks a GTM Architect, Expansion & Retention for its ShareGate product line. The organization creates software relied upon by over 15,000 businesses globally, including Microsoft 365 migration tools and management solutions, alongside the Workleap Agent platform.
This embedded engineering position operates within the go-to-market organization rather than back-office operations. The professional in this role will design, construct, and deploy artificial intelligence agents and agentic workflows intended to secure renewals and generate cross-sell pipelines by utilizing product usage, customer support, and renewal metrics. Responsibilities include building monitoring mechanisms for account health, automating outreach and scoring, collaborating with Revenue Systems, validating data via SQL, and establishing reusable pipeline modules that sales and account management teams can independently manage.
Ideal candidates possess a background in revenue operations, marketing operations, customer success operations, or go-to-market engineering. The position suits individuals comfortable with ambiguity and fast-paced environments who can translate technical builds into accessible operational playbooks.
Responsibilities
- Develop AI agents that continuously monitor renewal health and alert account managers regarding at-risk accounts with recommended actions
- Design and execute an agentic cross-sell motion that scores account fit, researches accounts, personalizes outreach, and routes interest to sales
- Partner with Revenue Systems to define required signals and validate data pipelines using SQL
- Replace manual processes with reusable pipeline modules and AI agents for sales and account management
- Own reporting on pipeline generation, conversion rates, renewal outcomes, and revenue impact while conducting controlled experiments
- Transform technical implementations into standard operating procedures, demos, and playbooks to secure team adoption
Requirements
- Background in RevOps, GTM operations, marketing operations, customer success operations, or GTM engineering with automation building experience
- Hands-on experience utilizing low-code orchestration tools such as n8n, Make, or Zapier
- Working knowledge of Python or TypeScript for API integrations and data transformations
- Experience with agentic tools, MCP connectors, and LLM workflow design including orchestration, tool use, and evaluation
- Proficiency in SQL to query and validate usage, support, and renewal data
- CRM familiarity, with HubSpot experience preferred
- Understanding of subscription business metrics such as renewal rates, net retention, and customer lifetime value
Qualifications
- Experience building AI-driven qualification or scoring systems
- Background in B2B SaaS environments featuring multiple product lines, ideally product-led or demo-led
- History of publishing technical content that simplifies complex systems
Core Skills
Benefits
- Base salary ranging from $110,000 to $140,000 CAD with regional adjustments
- On-target earnings of $120,000 to $155,000
- Long-term incentive program participation
- RRSP program
- Family health insurance
- Telemedicine services
- Annual wellness budget
- Flexible vacation policy
- Access to the Montreal office with twice-yearly in-person gatherings
- Access to Claude AI tools
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the internal job title for this position?
The internal title for this role is GTM Architect, Expansion & Retention.
What is the salary range for this role?
The base salary ranges from $110,000 to $140,000, with on-target earnings between $120,000 and $155,000, reflecting a Canada-wide compensation scale.
Where is the job located?
The posting indicates remote work with access to the employer's Montreal office and mandatory in-person gatherings twice a year.
What technical stack is used in this role?
The stack includes low-code orchestration tools like n8n, Make, or Zapier, Python or TypeScript, SQL on the data warehouse, and HubSpot CRM.
Sample Interview Questions
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