Alan Whitehead
Enterprise technology sales · Strategic accounts
Santa Monica, California · alan@alanwhitehead.com · alanwhitehead.com · LinkedIn
Professional profile
Enterprise technology sales professional with experience in higher education, public-sector cybersecurity and strategic accounts. My work includes institutional procurement, new-business development, renewal and expansion, and coordination across academic, technical, executive and commercial stakeholders.
A foundation in technical account management and current personal infrastructure and AI practice support informed customer conversations and collaboration with technical specialists.
Selected commercial experience
- Established an approved purchasing path with pre-negotiated pricing for individual campuses in a public university system at D2L.
- Developed a private-university platform replacement from cold outreach through an RFP to a seven-figure, multi-year agreement at D2L.
- Retained and expanded a public-university account and negotiated a signed seven-figure, long-term agreement at ProctorU.
Customer identities and sensitive commercial terms are generalized for public use.
Experience and recent activity
Family caregiving and independent technical practice
–present
- Personal work with Linux, Proxmox, Cloudflare-backed applications, Git and AI-assisted workflows.
- Define project requirements and operating constraints, use AI assistance for implementation, and review changes and results.
Cyberbit — Senior Account Executive, SLED, Western US
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- Developed state, local government and education opportunities for cyber-range training and readiness.
- Engaged security leaders and coordinated workshops, budget discussions, partner-supported procurement and formal evaluations.
- Advanced state opportunities through evaluation and procurement; they remained unsigned when I left.
Family caregiving
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ProctorU — Regional Vice President
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- Combined new-business development with strategic renewal and expansion work.
- Coordinated institutional and internal stakeholders around account requirements and commercial terms.
- Advocated for standards-based authentication, security evaluations and integrations, and secured funding for an external accessibility audit.
D2L — Senior Higher Education Sales Executive
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- Developed institutional opportunities through executive engagement, academic and technical evaluation, pilots, procurement and negotiation.
- Coordinated solutions engineering, product, finance and executive resources in complex buying processes.
- Built a private-university relationship from an initial conference conversation through sustained engagement, a pilot and an RFP to a contract.
D2L — Senior Enterprise Sales Executive, Webcasting and Mobile
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BlackBerry / Research In Motion — Senior Account Executive, Chalk Pushcast
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BlackBerry / Research In Motion — Senior Government and Strategic Account Manager
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BlackBerry / Research In Motion — Senior Technical Account Manager
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Selected experience across these BlackBerry / Research In Motion roles
- Worked across technical account management, government and strategic accounts, and enterprise sales.
- Supported enterprise messaging and BlackBerry Enterprise Server environments, with carrier and customer technical engagement.
Earlier technical foundation
Community-college IT work, followed by roles at Unisys and Netstar involving enterprise technology and messaging architecture.
Education
Associate Diploma in Information Technology
Southbank Institute of Technology · –
Current technical practice
Personal infrastructure operations; Cloudflare Workers, D1, Pages and Access across distinct projects; Git and GitHub; local and hosted AI workflows using Ollama, OpenClaw and Whisper. This AI-assisted personal practice supports informed conversations with technical stakeholders.