Director, Account Management - ShareGate

Job Description 

The Mission: Architecting the Next Chapter of ShareGate

ShareGate is a household name in the Microsoft ecosystem. For 15 years, we’ve been the "gold standard" for migration. Now, we’re doing something even more ambitious: evolving from a single-product tool into a comprehensive platform (Protect, Backup, and beyond) for the IT buyer. As the Director of Account Management, you aren't just overseeing a department; you are the lead architect of our retention and expansion engine. 

The Mandate: Humans + AI

Reporting to the CRO, you will lead the strategy for a customer base that already loves us. Currently, our motion is 100% human-driven. Your mandate is to identify where we can leverage AI automation to augment our people—removing the "robotic" work from our managers so they can focus on high-value human relationships. 

• Lead the Leaders: Manage a team of two managers who oversee our Account Management and Renewal squads. Coach them to move from order-takers to growth owners. 
• Modernise the Motion: Build the first version of our AI-augmented expansion playbook. You'll identify opportunities to use AI for customer health monitoring, automated renewal touches, and predictive cross-sell signals. 
• Design the Multi-Product Playbook: Define how we cross-sell new products (Protect and Backup) into an established base of thousands of IT pros. 
• Operationalize Excellence: From enterprise account planning to automated SMB motions, you will build the scalable structures that make $100M+ ARR look easy. 
• Cross-Functional Collaboration: Partner with Product and RevOps to ensure the feedback loop is tight, reducing churn and identifying new "wallet share" opportunities.

The Challenge: Renewal + Expansion

The "Migrate" motion is well-versed and successful. The "Protect" and "Backup" motion is the new frontier. The primary challenge is shifting the team from "handling a renewal" to "expanding a partnership" while simultaneously transitioning from a purely manual workflow to one powered by AI and automation. You’ll help us figure out how to get more out of our business and our people by embracing the next wave of tech.

Qualifications

• The SaaS Veteran: 10+ years in B2B SaaS, ideally supporting the IT/Technical persona. 
• The Leader of Leaders: 3+ years experience managing managers. You know how to scale yourself through others. 
• The AI-Forward Thinker: You aren't afraid of automation. You have a vision for how AI can make a GTM team more efficient and effective, and you’ve ideally experimented with AI tools in a professional setting. 
• The Scale Specialist: You’ve operated in (or helped build) a $100M+ ARR environment. 
• Direct & Execution-Oriented: You don't just "set direction"—you stay close to the business to ensure the discipline is there to win. 

Why Workleap?

We believe in working better. That applies to our products and our people. You’ll join a GTM leadership team that is collaborative, high-performing, and focused on building a generational Canadian tech company.