Director, Account Management - ShareGate
Barley
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
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.
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
As a tech-forward company, we leverage AI tools to enhance our recruitment process, while ensuring all hiring decisions remain human-led.
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
