Job Overview
Location
Canada - Remote
Job Type
Full-time
Category
Sales
Date Posted
May 14, 2026
Full Job Description
đź“‹ Description
- • As the Director of Account Management at ShareGate, you will serve as the lead architect of the retention and expansion engine, driving the evolution of ShareGate from a single-product tool into a comprehensive platform for IT buyers.
- • Day to day, you will lead a team of two managers overseeing Account Management and Renewal squads, coaching them to transition from order-takers to growth owners while building the first AI-augmented expansion playbook.
- • You will operate within Workleap, a Montreal-based tech company building AI-powered HR solutions and the leading Microsoft 365 migration and governance platform, trusted by over 20,000 companies worldwide.
- • In this role, you will learn to scale GTM operations in a $100M+ ARR environment, design cross-sell strategies for new products like Protect and Backup, and operationalize AI-driven automation to enhance customer health monitoring, renewal processes, and predictive cross-sell signals.
🎯 Requirements
- • 10+ years of experience in B2B SaaS, ideally supporting the IT/Technical persona
- • 3+ years of experience managing managers, with a proven ability to scale through others
- • Experience operating in or helping build a $100M+ ARR environment
- • Vision for how AI can improve GTM team efficiency and effectiveness, ideally with hands-on experimentation using AI tools in a professional setting
- • Direct, execution-oriented mindset—staying close to the business to ensure discipline and results
🏖️ Benefits
- • Join a collaborative, high-performing GTM leadership team focused on building a generational Canadian tech company
- • Work in a healthy, inclusive environment where curiosity, experimentation, and ownership are valued
- • Opportunity to express yourself, evolve creatively, and develop in an environment that adapts to your daily life and needs
- • Access to Workleap’s Candidate Experience Flow: Phone Screen → Virtual Interview (Microsoft Teams) → Work Sample → Job Offer
- • Leverage AI-enhanced recruitment tools while benefiting from human-led hiring decisions
Skills & Technologies
About Workleap Inc.
Workleap is a leading employee experience platform that empowers organizations to build a better workplace. Their integrated suite of solutions helps companies engage, develop, and recognize their employees. Key products include employee recognition and rewards, learning and development, and internal communications tools. By fostering a positive and productive work environment, Workleap aims to improve employee retention, boost performance, and drive overall business success. They serve a global clientele across various industries, helping them connect their people and achieve their strategic objectives through enhanced employee engagement.
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