Jim Knotts | Managing Partner
Jim is a technology and business strategist who helps highly regulated organizations modernize securely while navigating compliance, operational risk, and long‑term strategic objectives. As Managing Partner at Headway Strategy, he advises executive teams on aligning technology, security, compliance, and operations to support growth and resilience.
His background includes leading large‑scale enterprise cloud transformations, secure collaboration initiatives, and regulatory readiness programs across industries such as defense, aerospace, healthcare, finance, legal, and government. Jim brings deep expertise in Microsoft 365 and GCC High, CMMC and NIST 800‑171 readiness, ITAR and DFARS environments, cybersecurity strategy, and complex M&A or divestiture technology transitions. His approach emphasizes practical, business‑focused guidance that balances security, usability, governance, and continuity to help organizations operate confidently in demanding environments.
Previous Organization Experience
Jim has had a successful career supporting organizations across many different industries and geographies. Below are some of the organizations that Jim has been a part of, making a significant difference in their day-to-day operations and continued success
Previous Projects
Microsoft 365 GCC High Environment Build & Deployment
Implemented a new Microsoft 365 GCC High environment to accommodate a subset of client business directly related to government clients and ITAR-controlled CUI. The environment was deployed to support approximately 150 users.
Microsoft 365 GCC High Environment Build & Deployment
Implemented a new Microsoft 365 GCC High environment to accommodate a subset of client business directly related to government clients and ITAR-controlled CUI. The environment was deployed to support approximately 25 users.
Acquisition - Industrial Controls and Automation
Completed an acquisition for a manufacturing company supporting approximately 25 users including Microsoft Exchange Online, SharePoint Online, Teams, and OneDrive for Business
User Principal Name and Primary SMTP Rename
Assisted a client, due to an acquisition, convert 14,000 users to a new user principal name (Microsoft Active Directory & Microsoft Entra ID) and primary smtp address to match the new public organization branding. This included the testing and validation of over 5,000 applications organization-wide, collaborating with teams in the United States and India.
Skills & Keywords
Manufacturers
APC (American Power Conversion) • Apple • Aruba • Cisco • Dell • Eaton • HP • HPE • Lenovo • Logitech • Meraki • Microsoft • Polycom • Ubiquiti • Yealink
Cloud Providers & Services
Amazon Web Services • Google Cloud Compute • Google Workspace • Microsoft 365 Commercial • Microsoft 365 GCC (Government Community Cloud) • Microsoft 365 GCC High • Microsoft Azure Commercial • Microsoft Azure Government
Software
Apple Business Essentials • Apple iOS • Apple iPadOS • Apple MacOS • Asana • BitTitan MigrationWiz • Cisco Meraki • Cisco Room Systems • Cisco Webex & Calling • Cisco Umbrella • Connectwise Automate • Connectwise Manage • Connectwise ScreenConnect • Microsoft 365 • Microsoft Azure Conditional Access • Microsoft Endpoint Manager (Intune) • Microsoft Entra ID (Azure AD) • Microsoft Exchange Online • Microsoft Exchange Server • Microsoft IIS • Microsoft Office 365 • Microsoft OneDrive for Business • Microsoft SharePoint Online • Microsoft SharePoint Server • Microsoft SQL Server • Microsoft Teams & Teams Rooms • Microsoft Windows • Microsoft Windows Server • NinjaRMM • Okta • Power BI • Salesforce • SentinelOne Complete • SentinelOne Data Lake • SentinelOne Singularity • ShareGate Migrate • Tableau • Zoom (Meetings, Workplace, Rooms, and Phone)
Areas of Experience
Analytics Dashboards • Business Analysis • Business Continuity Planning • Business Operations • Business Reporting • Client Relations • CMMC (Cybersecurity Maturity Model Certification) • Compliance • Cost Benefit Analysis • Cybersecurity • Cybersecurity Event Crisis Management • Data Analytics • Data-Driven Decision Making • Datacenter Design • Disaster Recovery • Divestitures • Edge Network Security • Endpoint Security • IT Lifecycle Design & Management • IT Operations • ITAR (International Traffic in Arms Regulations) • Marketing • Master Planning • Mergers & Acquisitions • Network Design • Network Switching, Routing, & Wireless • Operational Model Creation • Policy Drafting • Product Lifecycle Management • Project Management • Project Planning • Regulatory Compliance • Service Management • Strategic Planning • Vendor Management • Vendor Negotiation
Industry Experience
Aerospace • Banking • Construction • Consumer Packaged Goods • Defense • Government (Local/Municipal) • Grocery • Healthcare • Legal • Manufacturing • Pharmaceutical • Real Estate • Retail • Transportation & Logistics