The goal and scope of Oakwood’s Microsoft 365: Roadmap To Success consulting engagement is to assist with your organization’s overall Microsoft Strategy.

During this two to four week engagement, Oakwood’s Microsoft Gold Certified Consultants will partner with your team to review your current state and help develop your future state plan(s) and timeline.  Throughout this process, Oakwood will facilitate several Deep Dive sessions into best practices and will complete a discovery of your current environment.


Step 1: Discovery

The Oakwood Team will engage with business and IT leadership to define your M365 goals and strategy. During this portion of the engagement, we will:

  • Identify Microsoft 365 applications that are currently in use.
  • Conduct in-depth discussions with stakeholders to understand what services are being used, how they are used and why.
  • Review current Active Directory (AD) and Tenant setup in order to recommend best practices and inform you of any ‘red flags’ that may exist.

Step 2: Deep Dive

Upon completion of the Discovery Phase, we’ll then move to a series of Deep Dive Sessions to discuss best practices of Microsoft 365 technologies including:

  • Discussions of current state and desired future state to meet your business needs.
  • Microsoft Licensing to provide any licensing options and cost savings opportunities.
  • Governance, Adoption, Change Management and Training.
  • Messaging, File Sharing and Collaboration.
  • Labels, Policies, Archiving and Retention.
  • Intune, Mobile Device and Application Management.
  • Windows Virtual Desktop, Remote Workforce.

Step 3: Deliverables

As part of this Professional Services engagement, Oakwood will deliver the following to you via a final presentation roadmap.

  • Discovery Document
  • 365 Maturity Roadmap Presentation
  • Training Resources
  • Present Timeline, Plan and Costs can include
    • Governance and Adoption
    • Migration to Exchange online SharePoint online, OneDrive, Teams
    • Security and Compliance implementation
    • Intune, MDM/MAM implementation
    • Windows Virtual Desktop implementation
    • 365 Application Managed Services

All of the above is covered within a $15,000 fixed fee engagement with Oakwood Systems Group.


Leave us a message below and one of Oakwood’s Microsoft 365 Team members will reach out to you to schedule a time to have a further discussion of your unique needs and timeframe.