About CurrentWare:

CurrentWare builds endpoint security, workforce analytics, and productivity software through BrowseReporter, BrowseControl, AccessPatrol, and enPowerManager. Our products are used by mid-market organizations across government, healthcare, financial services, manufacturing, education, and other security-conscious industries.

We recently launched the full CurrentWare Suite in the cloud and are now helping a large installed base of on-premises customers evaluate and navigate that transition. This role sits at the center of that opportunity.

The Role:

You will own our Tier 1 portfolio: roughly 30 accounts at $20K+ ARR, including several of our largest and most strategic customers.

Your mandate is to build white-glove relationships where customers see their CSM as a trusted partner rather than simply a vendor contact. That means understanding their environment, helping them interpret their usage data, working through policy and deployment questions, and identifying where CurrentWare can deliver additional value.

Two things make this role different from a standard enterprise Customer Success position.

You will own the cloud transition for your portfolio. Most of these customers are still on-premises. You will understand each customer's environment, constraints, and readiness, then build and execute the right path forward, including recognizing when remaining on-premises is the right answer.

You will own expansion. Renewal is the foundation, not the finish line. Cloud migrations, additional modules, license growth, and trials should emerge naturally from your understanding of the customer. You will build and manage that pipeline with the same discipline as a sales opportunity.

What You Will Do:

- Establish the right engagement cadence for each account, including monthly or bi-weekly touchpoints for the highest-touch relationships and meaningful quarterly engagement across the broader Tier 1 portfolio
- Engage pre-sale on strategic opportunities to understand the customer's objectives, environment, technical requirements,



and success criteria so onboarding begins with a clear plan
- Own onboarding end to end, working hands-on with customers through deployment planning, configuration, admin enablement, and training, while partnering with Support where deeper technical intervention is required
- Build and execute account-specific cloud migration plans, using renewals, upgrade conversations, and support interactions as natural opportunities to assess readiness and move customers forward
- Identify, qualify, and close expansion opportunities across additional products, license growth, cloud migration, and managed trials, and maintain an accurate expansion forecast
- Own renewal outcomes across your portfolio, including the save motion when an account signals churn: diagnose the underlying issue first, then identify the right lever
- Partner with Operations on renewal execution and with Support on escalations, stepping in directly when a technical issue becomes a relationship issue
- Bring the voice of the customer back into the business, including what customers need next, where they are encountering friction, and where the product should evolve

What We Are Looking For:

- 5+ years of experience in Customer Success, Account Management, or a hybrid CS/AE role owning mid-market, enterprise, or strategic accounts at a B2B software company.
- Demonstrated commercial ownership. You have carried a renewal, expansion, NRR, or similar revenue target and have a track record of delivering against it.
- Confidence discussing pricing, handling objections, navigating commercial conversations, and asking for the business.




- Experience leading customers through a meaningful technology or platform transition, ideally from on-premises to cloud. You understand the discovery, planning, stakeholder alignment, migration, and objection-handling required to manage change successfully.
- Robust technical fluency. You can confidently discuss deployment architecture, networking and firewall requirements, agent-based software, endpoint management, and IT security concepts with technical stakeholders.
- The ability to translate technical concepts clearly for non-technical buyers and executive decision-makers.
- Experience selling to or supporting IT, security, compliance, or related stakeholders, ideally in regulated or security-sensitive environments.
- Strong instincts for account health. You can look at engagement signals, product usage, support activity, and customer behavior and know which accounts need attention.
- Excellent written and verbal communication skills, with confidence presenting to both technical teams and senior decision-makers.

Nice To Have:

- Background in endpoint security, employee monitoring, DLP, workforce analytics, or adjacent software categories.
- Experience working with public sector, healthcare, financial services, or other regulated customers.
- Hands-on experience with Zoho CRM and Zoho Desk, or comparable CRM and support platforms.
- A history of building process, not just following it. We are continuing to develop our Customer Success playbook, and we want someone who will help shape it.

Why This Role: You will inherit an established portfolio of customers at a company entering an important new phase of growth.

The cloud transition represents one of the largest opportunities in the business, and this role will have meaningful influence over how we approach migration, retention, expansion, and strategic account management across our customer base.

For someone who succeeds in the role, there is meaningful scope to help shape the Customer Success organization and grow into broader team leadership.

📌 Customer Success Manager, Strategic Accounts (Canada)
🏢 Currentware
📍 Canada