Timothy Cashman

Principal Cloud Solution Architect empowering organizations through the delivery of strategic, requirements-driven Microsoft Copilot & Artificial Intelligence solutions and tools. Active TS/SCI with FSP Clearance

Reston, Virginia, United States

About

I’m a Principal Cloud Solution Architect with a passion for leading implementation projects that empower client companies, ensure successful user adoption, and drive business growth. As a seasoned AI specialist at Microsoft, I've championed the deployment and adoption of Copilot and Artificial Intelligence platform-based solutions via Azure AI within the Federal Government space, driving innovative AI solutions and ensuring optimal user engagement. My focus? Bridging tech and people, fostering a seamless integration of AI into daily workflows. Technology is always evolving to meet new market and user demands. With over 20 years of experience developing and executing projects for both public and private sector accounts, I know what it takes to meet those demands. I employ data-driven, stakeholder-centric approaches to surpass user expectations surrounding solution implementation and change management. I further utilize data insights to deliver customized solutions and tools while also ensuring high user adoption rates and empowering client teams through customized training programs. My belief that “none of us is as smart as all of us” directly influences my interactions with clients, executive leadership, and cross-functional teams. When I work with clients, I listen carefully to form an in-depth understanding of their current and future needs and bring Microsoft teams together to produce effective, applicable solutions. Seeing the immense value MS solutions have added to organizations motivates me to continue driving project success and delivering measurable results for Microsoft and our clients. I am always open to connect with likeminded professionals and share how Microsoft's AI products could support your organization’s success. Let's transform the way we work, together!

Experience

  • Microsoft (On-site)
    • Principal Cloud Solution Architect
      Mar 2023 - Present · 3 yrs 4 mos

      As a Principal Cloud Solution Architect at Microsoft, I lead strategic engagements across the Federal Government space to accelerate the adoption of Microsoft Copilot, Azure OpenAI, and AI-powered solutions. My focus is on aligning AI innovation with enterprise readiness—ensuring organizations not only deploy AI effectively, but do so securely, responsibly, and with lasting impact. I specialize in delivering tailored Copilot Workshops and hands-on guidance to help public sector agencies understand the capabilities and boundaries of Microsoft 365 Copilot. I emphasize the critical role of data governance in successful AI integration, working closely with stakeholders to ensure their information architecture, security posture, and compliance frameworks are ready for responsible AI use. This includes helping clients leverage Microsoft Purview, SharePoint Advanced Management, and other tools to enhance visibility and control over their data landscape. Beyond enablement, I guide the development and deployment of custom AI agents—both in Copilot and Azure OpenAI—designed to extend Microsoft platforms through integration with third-party systems like ServiceNow. These purpose-built agents help unlock new efficiencies, automate workflows, and deliver user-centric experiences rooted in real business needs. Whether driving change management initiatives, bridging technical and executive audiences, or building the connective tissue between Microsoft solutions and client systems, I am committed to helping public sector organizations realize the full potential of AI while upholding the highest standards of trust, security, and governance.

    • Senior Customer Success Manager
      Nov 2017 - Mar 2023 · 5 yrs 5 mos

      I served as a key partner and advisor on the creation of Microsoft's Customer Success Unit (CSU), working closely with CSU teams and executive leaders to positively impact enterprise organization and strategy. Following the successful CSU launch, I began and continue to manage account portfolio programs, communication, and operations for key government clients, directing solution adoption projects surrounding Microsoft's Modern Workplace solutions. • Facilitate timely, in-scope project delivery and solution implementation by establishing clear timelines, milestones, roles, and expectations for both Microsoft and client POCs. • Communicate regularly with private and public sector client executives to assess current alignment of business needs, IT environment, and MS solutions, making service expansion or adjustment recommendations as needed. • Work alongside Microsoft teams to ensure strategic alignment within account life cycle and drive successful client-specific initiatives. • Analyze usage data collected via built in pulse checks to identify gaps in tool capabilities and user awareness/adoption. Select Achievements/Projects • Accepted opportunity from Department of Interior IT leadership to turn around low usage and lead adoption efforts for 60K+ end user migration to Office 365. Engaged Microsoft-certified partner to create Teams awareness campaign across entire DOI. Awarded Microsoft Teams Accelerator Award for completed work. • Championed Teams deployment at Federal Reserve System; delivered platform demos, competitor comparisons, and change management plans to key organization leadership. Met 30-day challenge from OCIO after coordinating acceleration of early adopters and Teams. • Revamped under-performing Microsoft Teams initiative at Department of Education. Demonstrated platform legitimacy and expanded end user buy in by enhancing support visibility with Secretary & Undersecretary of Education and launching metric-driven awareness/marketing campaigns.

  • Customer Success Manager / Change Management Specialist at Bluescape Software
    May 2016 - Nov 2017 · 1 yr 7 mos

    I was recruited into this role and tasked with leading the formation of Bluescape’s Customer Success practice, including strategies, structures, and processes. After building out the practice/division, I served as an SME and mentor to CSMs and change management staff delivering implementation projects for private and public-sector organizations. • Engaged key executive stakeholders within client organizations; secured high solution use rates through corporate goal connection, staff education, and C-level evangelization. • Applied prior change management experience to direct select implementation projects as needed. • Authored industry white papers and case studies on Bluescape software in client organizations to drive intellectual capital and subject-matter expertise in marketing initiatives. Select Achievements/Projects • Transformed implementation efficiency and delivery by recognizing need for foundational change management and customer success practice/process definition. Plan now marketed as key differentiator to potential clients. • Secured contract renewal and expansion of licenses and services after serving as CSM for implementation at University of Texas at El Paso (UTEP).

  • Process Excellence & Change Enablement Consultant at Accenture
    Oct 2012 - May 2016 · 3 yrs 8 mos

    At Accenture, I held high-level oversight of strategy, operations, and resources for change management projects related to IT implementations/reorganizations. Functioning as project manager and consulting partner for federal government clients, I secured additional contract revenue by working closely with clients to identify their business pain points over contract lifecycle and present relevant solutions. • Supervised two direct reports, supporting individual talent development opportunities and handling performance management processes. Provided functional leadership to cross-functional project teams. • Kept project within budget as defined by proposal by applying proactive cost monitoring and management processes. Maintained full compliance with rigorous public-sector requirements. • Collaborated with internal and external/client teams to align project operations, communications, and logistics with client goals and structures. Select Achievements/Projects • Spearheaded change management and communications activities for Federally Facilitated Marketplace for Centers for Medicare & Medicaid Services (Affordable Care Act). Built out plan based on stakeholder assessment of 500 staff and redesigned training program. • Led team assessing impacted financial processes and hierarchies to enable successful GFEBS/SAP implementation at Walter Reed Hospital. • Appointed Project Manager for Defense Logistics Agency (DLA), overseeing implementation of new SAP software application to monitor pricing anomalies. Created jobs/roles and processes impacting 300+ DLA employees. Awarded additional contract work for post-implementation monitoring at client’s recommendation.

  • Associate at Booz Allen Hamilton
    Nov 2008 - Oct 2012 · 4 yrs

    I directed all project planning, preparation, and execution projects for major public sector IT implementations and organizational realignments. I ensured each project was successful and strategically aligned with the clients’ needs by conducting in-depth organizational assessments, stakeholder analysis, and data gathering activities. • Drove project/implementation success and secured stakeholder acceptance through creation of holistic, informative communications plans and effective organizational designs. • Crafted audience-driven campaigns with tailored messaging and accessible mediums; delivered recommendations for future client communication initiatives based on research. Select Achievements/Projects • Appointed as Change Lead for creation and establishment of new IRS Office of Online Services (OLS); developed and directed multi-channel communications campaign producing 58% increase in website traffic and 22% increase in “meet-and-greet” events attendance. • Led change activities for NY State Office of Social Services’ statewide implementation of new IT infrastructure. • Directed development and execution of Army Knowledge Online (AKO) Outreach Campaign generating 10%+ increase in AKO site utilization.

  • Consultant / Project Manager at Deltek
    Nov 2005 - Nov 2008 · 3 yrs 1 mo

    Led and developed corporate strategy for Fortune 500 and small business vendors targeting the public sector IT market. Led product strategy, business intelligence, research and analysis, and cross-functional employee teams while developing strategic business plans for client’s executive team approval