Resume / The full professional record

Alan Whitehead

Senior Enterprise Sales Executive
Strategic accounts · Hands-on AI & infrastructure

25+ years in technology and enterprise sales since 2008. Technical account management roots, President’s Club, seven-figure institutional SaaS agreements, and current hands-on work with AI agents and infrastructure.

Santa Monica, CA
Remote, hybrid, or onsite

Full details below. Client and customer identities are intentionally anonymized.

Professional summary

Senior enterprise sales executive with 25+ years in technology and enterprise sales since 2008. Spent 2004–2012 at Research In Motion / BlackBerry, moving from technical account management into enterprise sales. Exceeded a $1M+ annual quota and earned President’s Club selling Learning Management Systems to Higher Education; served as Regional VP of Sales, US West, owning a $10M+ territory for a regulated assessment platform; and built a $2.5M+ State, Local, and Education (SLED) cybersecurity pipeline. Won six- and seven-figure SaaS agreements through legacy displacement, security and compliance review, and system-wide procurement.

Currently hands-on with AI agents and infrastructure: runs a Proxmox environment of 30+ virtual machines and containers, with an operational control plane and a backup and recovery program. Directs AI agents through structured harnesses, defining goals, architecture, and boundaries, selecting models and reasoning depth by task, requiring tests and evidence, and using independent models for adversarial review; agents implement substantial parts of the code and configuration. Applies MEDDPICC and Challenger methods with first-hand technical context in evaluations involving executives, security teams, engineering, and procurement.

Professional experience

Business Systems, AI & Infrastructure · Mar 2024–Present

Independent Technology Consultant

Modernized a field-services client’s commercial operations; designs, directs, and operates AI-agent and infrastructure systems hands-on.

Key accomplishments
  • Field-services modernization: Rebuilt the commercial operations of an established, multi-decade field-services business around connected systems: inbound lead capture and CRM routing, automated pricing, programmatic invoicing, customer payments, custom email domains, and API-driven customer communications.
  • Operational control plane: Designed and operates a private, read-only monitoring and evidence service in typed Python (FastAPI, SQLite, Alembic) on Docker Compose, with AI agents implementing substantial parts under defined architecture and tests; least-privilege Proxmox API access, releases from reviewed commits with recorded rollback targets, and a crash-safe deploy journal that fails closed on recovery.
  • Backup and recovery program: Audited a Proxmox environment of 30+ virtual machines and containers (ZFS, Proxmox Backup Server, off-site configuration archive); produced a findings register, staged remediation, recovery runbooks, restore validation through the real backup data path, and a recovery-readiness report.
  • Agent harnesses and multi-model workflows: Directs coding and operational agents (Codex, Claude Code, OpenCode, OpenClaw) through persistent instructions, tool and production-authority boundaries, exit gates, evidence requirements, and a custom work-coordination service. Assigns high-reasoning models to planning, diagnosis, and adjudication; cost-efficient models to investigation and execution; and a separate model to adversarial review.

Cyberbit · Cybersecurity SaaS (post-PE investment) · Apr 2023–Feb 2024

Senior Account Executive, SLED

Built $2.5M+ SLED pipeline and reached finalist stage in competitive public-sector RFPs.

Key accomplishments
  • 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: Ran compliance-heavy evaluations involving CISOs, chief risk officers, legal teams, and procurement directors while the company restructured after private-equity investment.
  • Legacy displacement strategy: Built displacement cases against entrenched on-premise and legacy solutions, co-authoring executive business cases on ROI, total cost of ownership, and security.
  • Competitive RFP progression: Reached finalist stage in multiple high-value SLED and public-sector RFPs; one significant opportunity was awaiting customer signature when a company-wide reduction in force ended the role.

ProctorU (now Meazure Learning) · Regulated assessment · Jul 2017–Jul 2019

Regional VP of Sales, US West

Led a $10M+ western territory and negotiated a seven-figure, long-term agreement.

Key accomplishments
  • Strategic deal restructuring (seven-figure agreement): Formulated and negotiated a long-term remote-invigilation agreement with a key regulated account, restructuring the commercial model around a sustainable annual budget and commitment.
  • Territory ownership: Owned and expanded a $10M+ western regional territory of 50+ regulated institutional and public-sector accounts.
  • Proof-of-concept design: Designed hands-on, multi-stakeholder proof-of-concept workshops with engineering, product, and compliance decision-makers, converting pilots into multi-year enterprise agreements.
  • Multi-threaded alignment: Managed matrixed institutional buying committees, aligning CISOs and academic leadership around centralized data protection and student identity-verification standards.

D2L (Desire2Learn) · Learning Management Systems · Jul 2012–Jul 2017

Senior Sales Executive

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

President’s Club. Exceeded a $1M+ annual quota through higher-education displacements, global programs, and master procurement placement.

Key accomplishments
  • Quota performance and President’s Club: Exceeded a $1M+ annual quota and earned President’s Club recognition; closed $300K+ annual SaaS agreements with private universities and global non-profit organizations.
  • Legacy displacement at a large private religious university (seven-figure agreement): 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.
  • Culturally aligned executive engagement: Earned trust under close cultural and financial scrutiny on campus and at national conferences, tailoring executive engagements to institutional values, including private, alcohol-free executive events.
  • Global faith-based organization platform win: Used institutional trust and account-level relationships to win a global enterprise training contract. Coordinated technical validation of availability, scale, and localization requirements for personnel across a large international footprint; the delivery architecture was later 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 (seven-figure agreement): 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 extended evaluation and pilot; the resulting account footprint remains active, referenceable, and revenue-generating more than twelve years later.

Research In Motion / BlackBerry · United States · From Sep 2009

Senior Account Executive

Relocated to the United States to join a business BlackBerry had acquired. Sold Chalk Pushcast mobile-learning software to enterprise, government, and education customers across the Central and Western United States and Canada, from new-business prospecting through purchase order and ongoing account management.

Research In Motion / BlackBerry · Asia Pacific · 2008–2009

Senior Government and Strategic Account Manager

Responsible for direct sales and management of the government and strategic account business in Asia Pacific; coordinated the Australian sales and marketing team and carrier and channel partners on government sales.

Research In Motion / BlackBerry · 2004–2008

Senior Technical Account Manager

National technical pre-sales for a major mobile carrier, with additional sales responsibility; the technical foundation for the commercial career that followed.

Earlier technology foundation · c. 1998–2004

IT and Technology Roles

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

Technical skills

Current and hands-on, in personal infrastructure and client work. AI agents implement substantial parts of the code and configuration; goals, architecture, boundaries, model selection, verification, and consequential decisions are owned directly.

  • AI agents and models: Agent harnesses (persistent instructions, access boundaries, exit gates, evidence requirements); planner, worker, and independent-reviewer workflows; model and reasoning-depth selection by task, latency, context, and cost; Codex, Claude Code, OpenCode, and OpenClaw; OpenAI, Anthropic, and DeepSeek models; open-weight models through Ollama; LiteLLM routing; MCP, REST APIs, and webhooks; local Whisper transcription.
  • Infrastructure and operations: Proxmox VE, Proxmox Backup Server, ZFS, Linux, Docker Compose, Caddy (TLS), Tailscale, and Prometheus; least-privilege API access, backup verification, restore rehearsal, and recovery runbooks.
  • Software and integration: Python (FastAPI, SQLAlchemy, Alembic, pytest), Bash, Node.js, Git and GitHub, and Cloudflare Pages and Workers.

Core skills

  • Enterprise sales: New-logo acquisition, strategic account development, MEDDPICC and Challenger methods, multi-million-dollar pipeline management, buying-committee and executive alignment (C-suite, IT, security, procurement), RFP/RFQ strategy, channel co-selling, and forecast discipline.
  • Markets sold into: Higher Education (Learning Management Systems and EdTech), regulated assessment, and State, Local, and Education cybersecurity.
  • Sales systems: Salesforce, HubSpot CRM, LinkedIn Sales Navigator, and Gong.

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 and clearances

  • Coursework in Information Technology, Southbank Institute of Technology
  • Clear 2026 DOJ background check | LiveScan fingerprinted