Alan Whitehead

Enterprise sales / Technology advisory

Complex deals.
Real systems.
One perspective.

I’m Alan Whitehead. I bring technical depth to enterprise sales—and a commercial purpose to the systems I build.

Alan Whitehead

25+ years in technology.
Still hands-on. Still curious.

01 / Experience mapSelect a connection ↙
01Enterprise salesRevenue & relationships 02Technical trustSecurity & procurement 03Systems & AIInfrastructure & automation

The commercial perspective

Institutional buying committees. Legacy displacement. Agreements worth staying for.

Explore the deal history

The connection between them

Work through architecture, security, and procurement with the people responsible for saying yes.

Inside a system-wide procurement win

The hands-on perspective

Private infrastructure, agent orchestration, model routing, and custom tooling for business workflows.

Explore the technical work

Santa Monica, CA · Open to senior sales roles & selective advisory work

Let’s talk
$2.0MTotal contract value
Ten-year agreement $500KAnnual contract value
Legacy platform displaced $2.5M+Pipeline built
Under 12 months
Nearly 20 yearsIn complex enterprise sales
From a foundation in IT

02 / Selected work

Where the two
perspectives meet.

The work ranges from getting a difficult agreement over the line to connecting the systems behind a business.

Enterprise sales / Learning Management Systems

Replace the system.
Earn the institution’s trust.

A six-month RFP. A full-day, 50-stakeholder demonstration. A deeply embedded homegrown incumbent.

Technology advisory / 2024–Present

Connect the tools.
Make the business work.

CRM routing, automated pricing, invoicing, and customer payments for an established field-services business.

See all selected commercial work

03 / Current technical practice

The lab keeps
the thinking honest.

I work directly with infrastructure and the systems around AI: agent workflows, model routing, context, tools, and validation. That makes architecture and integration conversations concrete.

Inside the systems
03Models & agentsOrchestration · Model routing · Tool use02Software & automationPython · Bash · REST APIs01InfrastructureProxmox · Docker · ZFS · Linux

04 / The through line

Technical roots.
Commercial range.

From IT and technical account management to strategic accounts, enterprise sales leadership, and technology advisory. EdTech centered on Higher Education; cybersecurity served State, Local, and Education markets.

Read the full career
  1. c. 1998IT & technology

    Community college IT, then roles including Unisys.

  2. 2004–2008Technical Account Management

    Research In Motion / BlackBerry. A technical, customer-facing foundation.

  3. 2008 onwardStrategic Account Management & enterprise sales

    The move into strategic commercial account ownership at Research In Motion / BlackBerry.

  4. 2012–2024Enterprise sales & leadership

    Learning Management Systems, EdTech, assessment, and cybersecurity. Higher Education focus in EdTech; State, Local, and Education customers in cybersecurity. Family caregiving break: 2019–2023.

  5. 2024–PresentTechnology advisory

    Business modernization and continued systems, AI, and automation work.

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A complicated evaluation?
An opportunity worth building?

Let’s talk