# Alan Whitehead

**Enterprise Account Executive & Technology Consultant**

Santa Monica, CA | [alan@alwhitehead.com](mailto:alan@alwhitehead.com) | [linkedin.com/in/alwhitehead](https://www.linkedin.com/in/alwhitehead/) | [alwhitehead.com](https://alwhitehead.com/)

Remote, Hybrid, or Onsite

## Professional Summary

Enterprise Account Executive with 25+ years in technology, including nearly two decades in complex commercial roles. Enterprise sales and leadership span Learning Management Systems, EdTech, assessment, and cybersecurity, with a significant Higher Education focus in EdTech and State, Local, and Education (SLED) customers in cybersecurity. Experience includes six- and seven-figure SaaS agreements, legacy displacement, and system-wide procurement. Current hands-on work includes AI systems engineering and automation.

Combines sales methodology (MEDDPICC, Challenger Sale) with hands-on work in virtualization, network infrastructure, AI systems, and agent orchestration to work through technical evaluations with executives, engineering teams, and procurement.

## Professional Experience

### Independent Technology Consultant & Enterprise Advisor | Digital Transformation & Infrastructure Advisory | Mar 2024–Present

- **Legacy-to-cloud digital overhaul:** Orchestrated the complete business and operational modernization of a legacy, multi-decade field-services enterprise. Built and integrated an automated tech stack spanning custom CRM routing, programmatic invoicing, dynamic automated pricing, and instant-deposit customer payment gateways.
- **Lead-generation and funnel automation:** Engineered automated local inbound lead pipelines that accelerated customer-acquisition velocity. Deployed secure custom email domains, API-driven customer communication layers, and targeted digital marketing schemas.
- **Hands-on AI and hypervisor infrastructure R&D:** Build and experiment with AI systems in a private lab: local inference, hosted model services, agent orchestration, task decomposition, context management, tool use, model routing, validation, and fallback paths. Work spans Ollama, Mistral, OpenAI, Anthropic, Codex, OpenClaw, OpenRouter, LiteLLM, Python, MCP, REST APIs, and webhooks for integration and business-process modeling.
- **Systems architecture engineering:** Provisioned and managed private infrastructure using Proxmox virtualization, Docker containerization, ZFS storage, network segmentation (VLANs), and identity and access controls.

### Senior Account Executive, SLED | Cybersecurity SaaS Platform (Post-PE Investment) | Apr 2023–Feb 2024

- **Greenfield territory pipeline:** Generated $2.5M+ SLED pipeline in under 12 months, including $1.2M+ qualified within the first two quarters, in a completely unmapped Western US territory.
- **Channel and alliance development:** Co-sold with national public-sector channel partners to extend reach into state and local government accounts; represented the platform at leading public-sector technology conferences.
- **Complex procurement navigation:** Directed compliance-heavy evaluation cycles simultaneously involving CISOs, chief risk officers, legal teams, and procurement directors, de-risking sales cycles through intense post-investment restructuring.
- **Legacy displacement strategy:** Unseated entrenched on-premise and legacy solutions by co-authoring executive business cases quantifying structural ROI, lower total cost of ownership, and the security advantages of modern, specialized SaaS platforms.
- **RFP pipeline leadership:** Positioned multiple high-value SLED and public-sector RFPs for final contract negotiation before a company-wide reduction in force.

### Career Break — Family Caregiving & Technical Continuity | 2019–2023

Stepped back from full-time work for family caregiving priorities, including an extended period abroad, while maintaining hands-on Linux/virtualization proficiency; returned directly to a high-intensity enterprise AE role in 2023.

### Regional VP of Sales, US West | EdTech / Regulated Assessment Platform | Jul 2017–Jul 2019

- **Strategic deal restructuring ($2.0M TCV):** Formulated and negotiated a 10-year remote-invigilation agreement with a key regulated account, trading an aggressive annual price point for contractual longevity and a decade of competitive lockout.
- **Territory leadership:** Owned and expanded a $10M+ western regional territory of 50+ regulated institutional and public-sector accounts.
- **Technical trial optimization:** Designed hands-on, multi-stakeholder proof-of-concept workshops uniting engineering, product, and compliance decision-makers, converting speculative pilots into multi-year enterprise agreements.
- **Multi-threaded alignment:** Managed complex, matrixed institutional buying committees, aligning security-centric CISOs and academic leadership around centralized data protection and student identity-verification standards.

### Senior Sales Executive | Learning Management Systems / EdTech (Venture-Backed Scale-Up) | 2012–Jul 2017

Senior Higher Education Sales Executive (2013–Jul 2017) · Senior Enterprise Sales Executive, Webcasting & Mobile (2012–2013)

- **Legacy displacement at a large private religious university ($1.5M TCV):** Spearheaded a six-month RFP and sales cycle to unseat a highly customized, multi-decade homegrown platform. Defeated a regionally dominant incumbent with native geographic advantages by managing a full-day, 50-stakeholder live demonstration and establishing direct CEO-to-VP alignment.
- **High-EQ client advocacy:** Overcame intense cultural and financial scrutiny on campus and at national conferences; orchestrated tailored executive engagements that respected institutional beliefs, including private, alcohol-free executive events, to establish durable peer trust.
- **Global faith-based organization platform win:** Leveraged institutional trust and account-level relationships to win a global enterprise training contract. Structured a high-availability, zero-downtime framework supporting personnel across a vast international footprint; the architecture was subsequently adopted for additional high-stakes global training programs.
- **Master procurement placement, large public university system:** Managed a system-wide evaluation with the system's central procurement office. Won placement on the approved master buying vehicle, eliminating duplicative security, legal, compliance, and custom-pricing reviews for individual campuses.
- **Homegrown platform replacement at a private online university ($1.0M TCV):** Unseated a homegrown learning engine by methodically resolving deep data-security, compliance, and academic-migration concerns with the university's CIO and security teams over several months.
- **Faculty adoption de-risking:** Addressed critical faculty adoption concerns by demonstrating the platform's proprietary content-import engine, ensuring course consistency and retention visibility to protect university tuition margins.
- **Major private university capture (12+ year account lifecycle):** Initiated contact through persistent cold outreach and on-site alignment at a national higher-education conference. Navigated a complex nine-month evaluation and pilot; the resulting account footprint remains active, referenceable, and revenue-generating more than twelve years later.

### Strategic Account Manager | Research In Motion / BlackBerry | 2008 transition

Moved into Strategic Account Management in 2008, shifting from technical account management to strategic commercial account ownership and enterprise sales.

### Technical Account Manager | Research In Motion / BlackBerry | 2004–2008

Worked as a Technical Account Manager at Research In Motion / BlackBerry from 2004 through 2008, before moving into Strategic Account Management and enterprise sales.

### IT and Technology Roles | Earlier Technology Foundation | c. 1998–2004

Began IT work at a community college around 1998, followed by technology-company roles including Unisys.

## Technical Fluency & Credibility

Hands-on systems work supporting technology advisory and conversations with CTOs, CISOs, and enterprise architects.

- **AI agents and automation:** AI systems engineering in a private lab: agent orchestration and task decomposition with Codex, OpenClaw, and Python; model selection and routing through OpenRouter, LiteLLM, local endpoints, and hosted services; tool use through MCP, REST APIs, and webhooks; context management, validation, and fallback paths.
- **Audio / voice processing:** Local Whisper ASR turns audio into text on local infrastructure before transcripts enter downstream workflows.
- **Enterprise infrastructure:** Hypervisor management (Proxmox VE), Docker containerization, ZFS storage, Linux administration, API validation, VLANs, and IAM; fluency in GDPR/FERPA data-privacy considerations.
- **Development and tooling:** Python scripting, programmatic Bash automation, version control (Git), and REST API integration testing.

## Core Skills

- **Enterprise sales:** New-logo acquisition, strategic account hunting, MEDDPICC execution, multi-million-dollar pipeline management, cross-functional executive alignment (C-suite, VP Engineering, IT, purchasing), RFP/RFQ leadership, forecast discipline.
- **Strategic verticals:** Learning Management Systems, EdTech and Higher Education, assessment, cybersecurity for SLED customers, cloud infrastructure, and AI/automation tooling.
- **Sales systems:** Salesforce, HubSpot CRM, LinkedIn Sales Navigator, Gong, generative-AI enablement platforms.

## Community Leadership

- **PTA Executive Committee (Auditor), Franklin Elementary (SMMUSD):** Elected 2026. Fiscal oversight for the largest elementary school, and third-largest school overall, in the Santa Monica-Malibu Unified School District.
- **Youth Rugby Coach, Santa Monica Rugby Club (2024–Present):** Coaching and mentoring 15–20 youth athletes. USA Rugby Level One certified.
- **Coach & Match Official, AYSO Santa Monica (2022–Present):** SafeSport Trained (U.S. Center for SafeSport); Concussion Awareness certified.

## Education, Background & Clearances

- Coursework in Information Technology — Southbank Institute of Technology
- Clear 2026 DOJ background check | LiveScan fingerprinted