Technical lead, Microsoft SSE Program (Security Service Edge)

Position Type: Contract (6 Months to start, solid possibility of extension)

Location: Toronto preferred, remote (Canada-wide)

Must be eligible to work in Canada

Roles and responsibilities:

We are seeking a highly experienced Contract Microsoft SSE Program Lead to lead the planning, design, implementation, and adoption of Microsoft's Security Service Edge (SSE) platform across the organization.

In this role, you will serve as the primary technical and project lead for our SSE initiative, partnering closely with Infrastructure, Security, Cloud Services, Network Services, Endpoint Management, Identity & Access Management, and business stakeholders to modernize secure access to corporate applications and resources.

You will establish the roadmap, technical architecture, governance model, implementation strategy, and deployment plan for Microsoft SSE capabilities, including Microsoft Entra Internet Access and Microsoft Entra Private Access. The ideal candidate can comfortably drive strategic discussions with leadership, coordinate activities across cross-functional technical teams, and collaborate directly with external implementation partners and Microsoft resources.

Key Responsibilities

Program Leadership & Governance

- Lead the Security Service Edge (SSE) initiative from initial planning through implementation and operational transition.
- Develop and maintain the SSE roadmap, implementation plan, project timeline, and strategic objectives.
- Act as the primary technical point of contact between internal stakeholders, Microsoft resources, and external implementation partners.
- Drive program governance, status reporting, risk management, issue resolution, and executive communications.
- Design adoption strategies that minimize business disruption while maximizing security posture improvements.

Solution Architecture & Design

- Design and validate target-state Microsoft SSE architecture aligned with enterprise security and cloud modernization goals.




- Develop target-state designs for Microsoft Entra Internet Access, Microsoft Entra Private Access, Zero Trust Network Access (ZTNA), Conditional Access integrations, and identity-driven application access.
- Evaluate legacy VPN modernization or replacement opportunities and define secure web traffic inspection and routing practices.
- Ensure architectural alignment with existing Azure, Microsoft 365, Intune, Defender, and Entra environments.
- Establish operational support requirements, governance standards, monitoring practices, and procedures.

Security & Zero Trust Enablement

- Advance the organization's Zero Trust strategy through identity-first access controls.
- Partner with Security teams to define access policies covering applications, web access, device trust, and user risk.
- Evaluate and recommend enhancements to secure access architectures and remote connectivity models.
- Participate in security reviews, risk assessments, and design validations to meet compliance and risk requirements.

Vendor & Stakeholder Management

- Coordinate activities among managed service providers, internal technology teams, and vendor partners.
- Facilitate architecture workshops, design reviews, and stakeholder planning sessions.
- Manage project deliverables, dependencies, and expectations, delivering regular status updates to technology leadership.

Project Delivery & Change Management

- Manage associated project plans, work breakdown structures, risk registers, decision logs, and milestones.
- Coordinate pilot deployments, user acceptance testing, rollout activities, and operational readiness reviews.




- Support knowledge transfer and operational handoff to internal support teams, delivering standardized documentation and governance artifacts.

Key Deliverables
- Execute a strategic roadmap for Microsoft SSE implementation.
- Document target-state SSE architecture and governance models.
- Deliver pilot and production deployment plans for Microsoft Entra Internet Access and Microsoft Entra Private Access.
- Establish operational support processes, standards, and knowledge transfer materials.
- Define strategy for reducing reliance on legacy remote access technologies.
- Provide executive-level reporting on program progress, risks, and strategic outcomes.

Required Qualifications

- 8+ years of enterprise experience in infrastructure, cloud security, networking, or identity and access management (IAM).
- Proven track record leading complex security transformation or network modernization initiatives.
- Hands-on experience designing and deploying Microsoft security and identity solutions.
- Deep technical understanding of:
- Microsoft Entra ID & Conditional Access
- Microsoft Intune & Microsoft Defender
- Zero Trust Architectures
- Enterprise Networking Concepts
- Direct experience working with vendor implementation partners and Microsoft technical resources.
- Strong cross-functional coordination, facilitation, stakeholder management, and communication skills.

Preferred Qualifications

- Direct experience implementing Microsoft Security Service Edge (SSE), including Microsoft Entra Internet Access, Microsoft Entra Private Access, and Global Secure Access.
- Expertise in Secure Access Service Edge (SASE) and Zero Trust Network Access (ZTNA).
- Familiarity with legacy VPN architectures and migration/modernization strategies.
- Experience operating within enterprise cloud environments (Microsoft Azure) and regulated industries (e.g., Financial Services, Insurance).
- Relevant Microsoft security or cloud certifications.

📌 Infrastructure Lead (Canada)
🏢 Randstad Digital
📍 Canada