Senior Cloud

18 hours ago

Toronto, Ontario, Canada Jolera Inc. Full time
Who We Are Jolera is a global technology powerhouse, one of the fastest-growing Global Systems Integrators (GSI) and Managed Security/Service Providers (MSP/MSSP) in the world. With 650+ experts across 15 countries, we deliver secure, scalable, and intelligent solutions that help organizations modernize, protect, and accelerate their business. Our clients span enterprise, mid-market, and channel partners across North America and Europe. We specialize in complex transformation work across cloud, infrastructure, networking, cybersecurity, and AI-enabled operations. If you're passionate about solving difficult technical challenges, leading migrations at scale, and working directly with enterprise customers, you'll feel at home here.
Who You Are We are seeking a Senior Cloud & Infrastructure Migration Architect who combines deep hands-on technical expertise with strong customer-facing consulting skills. This role is ideal for seasoned professionals from large MSPs, GSIs, or cloud integrators who can both design and execute enterprise-grade migrations across hybrid environments.

You will lead complex transformation initiatives, working directly with customer IT teams, business stakeholders, and Jolera delivery units to modernize infrastructure, move workloads to cloud platforms, and transition from legacy to next-generation architectures.

This is a high-impact, hands-on architecture role. You will run workshops, define migration roadmaps, create runbooks, and still dive into the CLI to solve the hardest technical problems.   What You Will Do Customer Engagement & Architecture
  • Lead discovery workshops with customer architects, infrastructure owners, and leadership teams to understand current-state environments.
  • Translate business and technical requirements into actionable migration architectures and execution plans.
  • Develop detailed migration runbooks, playbooks, and technical designs for hybrid cloud, on-premises, and multi-site environments.
Migration Execution & Hands-On Delivery
  • Perform deep, hands-on migration work including:
  • Active Directory consolidations using Quest
  • File/Print migrations into Azure
  • SQL database migrations
  • Azure Migrate, CloudEndure, and associated tooling
  • Design and execute network migrations involving routing, switching, wireless, SD-WAN, and firewall transitions (Meraki → Check Point/Fortinet).
  • Troubleshoot complex issues across networking, identity, security, compute, and cloud workloads—working at both architectural and engineering levels.
  • Provide direct onsite or remote guidance during cutovers, go-lives, and operational transitions.
Cross-Functional Leadership
  • Serve as the senior technical authority throughout migration programs.
  • Collaborate with Jolera's SOC, NOC, cloud, and transformation teams to ensure smooth execution.
  • Mentor and guide internal technical teams, helping build repeatable migration accelerators and reference architectures.
  • Communicate risks, progress, architecture decisions, and business impacts to CIOs, CTOs, and senior stakeholders.
Documentation & Knowledge Transfer
  • Produce high-quality architecture diagrams, migration plans, test scripts, and validation reports.
  • Create repeatable migration patterns, playbooks, and best-practice guides to support Jolera's global modernization practice.

Qualification: Technical Expertise (10–20+ years)
  • You have deep, real-world experience delivering hands-on enterprise migrations, ideally within MSP/GSI or integrator environments.
  • You bring expertise across:

Infrastructure & Identity

  • Active Directory, Group Policy, domain consolidations
  • Quest migration tools
  • File/Print, permissions restructuring, NTFS/NAS migrations
  • SQL Server modernization and migration practices

Cloud Platforms

  • Azure (core requirement)
  • Microsoft 365
  • AWS (nice to have)
  • Azure Migrate, CloudEndure, AD Connect, hybrid identity architectures

Networking & Security

  • Routing, switching, VLANs, ACLs, DNS, DHCP
  • SD-WAN technologies (Meraki, Fortinet, Cisco, etc.)
  • Wireless (Enterprise)
  • Firewall migrations: Meraki → Check Point/Fortinet
  • Understanding of segmentation, zero-trust, and cloud network design

Migration Tooling

  • Quest, Azure Migrate, CloudEndure, ADMT, Robocopy, DFSR
  • Scripting (PowerShell preferred)

Consulting & Leadership Skills

  • Comfortable presenting to CIO/CTO-level stakeholders
  • Capable of leading workshops, whiteboard sessions, and design reviews.
  • Operates independently in complex, multi-vendor, multi-region environments.
  • Strong communicator with exceptional documentation and customer engagement abilities.

Preferred Qualifications
  • Microsoft Azure Architect Expert
  • AWS Solutions Architect
  • Cisco CCNP/CCIE
  • Check Point CCSA/CCSE
  • MSP/GSI consulting experience
  • Experience with cross-tenant migrations, integrations, or carve-outs

Why Jolera
  • Work on high-impact global transformation projects.
  • Be part of a fast-scaling modernization practice with significant career growth.
  • Collaborate with top-tier technical experts across 15 countries.
  • Flexible working arrangements and contract or full-time options.
  • A culture built on trust, autonomy, and innovation.
At Jolera, we are committed to creating a diverse, equal and inclusive. Our goal is to attract and retain the best talent while embracing diversity in all its forms. We value and respect differences in ethnic background, gender, age, religion, identity, disability, or any other characteristic protected by applicable law.

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