Professional Summary
Seasoned Enterprise Account Executive with a definitive track record of closing six- and seven-figure SaaS contracts across AI, cybersecurity, EdTech, and highly regulated institutional markets. Proven expert in orchestrating complex legacy displacements, navigating multi-layered governance and compliance reviews, and building system-wide procurement vehicles. Combines disciplined sales methodology (MEDDPICC, Challenger Sale) with hands-on, architect-level technical fluency in virtualization, network infrastructure, and private AI pipelines — eliminating technical friction, engaging C-suite executives peer-to-peer, and accelerating enterprise deal velocity.
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 & 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 & hypervisor infrastructure R&D: Maintain an active enterprise-grade private lab for live-fire simulation of modern engineering architectures. Developed local LLM and AI-agent pipelines (Ollama, Mistral, OpenClaw framework) with Anthropic and OpenAI REST API integrations to model business-process automations.
- Systems architecture engineering: Provisioned and managed localized cloud-equivalent platforms using Proxmox virtualization, Docker containerization, ZFS high-availability storage arrays, and strict network segmentation (VLANs, IAM controls, data-privacy compliance).
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 — with over $1M forecasted for close in H1 2024, in a completely unmapped Western US territory.
- Channel & 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 to 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; fully ramped return 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 unprecedented contractual longevity, guaranteeing multi-million-dollar long-term revenue and locking out competitors for a decade.
- Territory leadership: Owned and expanded a high-gravity $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 SaaS (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 6-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 bulletproof 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 and creating an unhindered procurement channel.
- 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 9-month evaluation and pilot; the resulting account footprint remains active, referenceable, and revenue-generating 12+ years later.
Technical Fluency & Credibility
Active systems and architectures used to consult on digital transformations and establish instant credibility with CTOs, CISOs, and enterprise architects:
- AI agents & automation: Self-hosted LLM pipelines (Ollama, Mistral) and autonomous AI-agent orchestration via OpenClaw with direct Anthropic/OpenAI integrations, webhooks, and Python-based custom skill architectures.
- Audio / voice processing: Local Whisper ASR pipelines for automated, high-precision transcription models.
- Enterprise infrastructure: Advanced hypervisor management (Proxmox VE), Docker containerization, ZFS storage arrays, secure Linux administration, API validation, network segmentation (VLANs), identity and access management (IAM), and GDPR/FERPA data-privacy architectures.
- Development & tooling: Python scripting, programmatic Bash automation, version control (Git), and REST API integration testing.