Gary W.

Agentic AI & Enterprise Platforms Leader | Customer-Centered AI Transformation | Building AI-First Operating Models

Seattle, Washington, United States

About

AI Enablement | GenAI Transformation | Enterprise AI Operating Models | AI Governance | Adoption at Scale AI enablement and transformation leader driving enterprise GenAI adoption from strategy to execution. I help organizations turn AI ambition into operating reality. My work focuses on enabling AI at scale through clear operating models, governance, and hands on adoption so AI delivers outcomes, not pilots. I am known for building and scaling AI programs that align executives, operators, and builders. Whether standing up an enterprise AI Center of Excellence, operationalizing agentic and RAG based workflows, or embedding AI into post sales and service delivery, I bridge vision and execution to accelerate what works and retire what does not. Today, I advise and enable AI adoption across 300 plus business units, guiding leaders on GenAI strategy, governance, investment discipline, and measurable ROI. In parallel, I lead AI transformation inside an operating SaaS business, where AI driven workflows reduced backlog by 60 percent, cut MTTR from weeks to days, and raised NPS to 100. My edge is enablement. I do not just introduce tools. I build the systems around them. Adoption playbooks, governance frameworks, champion networks, operating standards, and workflow level change that sticks. My work spans AI strategy, operating model design, adoption execution, and cultural transformation. I help organizations define where AI belongs, how it should be governed, and how teams actually use it day to day. Strengths and Focus Areas - AI enablement and enterprise adoption - GenAI transformation and operating models - AI governance, risk, and responsible adoption - Agentic workflows and RAG knowledge systems - AI for post sales, customer experience, and service delivery - Champion programs, change leadership, and scale enablement - Executive advisory and cross functional influence Builder. Operator. AI Enablement Leader. Open to conversations on AI enablement leadership, enterprise AI transformation, and roles focused on scaling GenAI adoption with discipline, trust, and measurable impact.

Experience

  • AssetWorks Inc (Remote)
    • Head of Agentic AI & Automation | AI Product Champion
      Jan 2026 - Present · 6 mos

    • Manager, Customer Care & GenAI Strategy Advisor
      Jul 2023 - Jan 2026 · 2 yrs 7 mos

      - Built AssetWorks’ first remote-first support team, scaling from a single engineer to a high-performing global group and creating the playbook for future 24x7 coverage. - Launched the Customer Advocate Program, streamlining upgrades, environment planning, and hosting coordination; reduced MTTR from 6–8 weeks to <2 weeks and raised NPS from 65 to 100 in two quarters. - Rolled out GenAI adoption company-wide, onboarding 80+ engineers and QA staff to Amazon Q and Copilot in a single week; created champion programs, KPIs, and prompt engineering guides to sustain adoption. - Designed AI-powered workflows integrated with Zendesk, Jira, Confluence, and Datadog—automating bug filing, knowledge base creation, meeting notes, and escalation triage—saving 15+ hours weekly. - Implemented a RAG-based knowledge retrieval system, cutting average troubleshooting time by 40% and boosting first-contact resolution. - Introduced intelligent swarming powered by GenAI triage, reducing escalations by 67% and accelerating case resolution. - Developed an AI-powered TAM framework that automated account health summaries and cut QBR prep time by 80%, enabling proactive engagement with strategic accounts. - Partnered cross-functionally with Product, Sales, and Engineering to turn AI-driven customer insights into roadmap improvements and ensure voice-of-customer impact.

  • Founding Member, AI/ML Center of Excellence (CoE) at Volaris Group
    Jan 2025 - Present · 1 yr 6 mos

    - Selected as a founding member of Volaris’ AI/ML CoE, advising 300+ global business units on enterprise AI strategy, enablement, and responsible adoption. - Developed scalable frameworks—including AI playbooks, onboarding templates, and discovery workbooks—used to identify and deliver high-impact GenAI use cases across support, product, and engineering. - Introduced VibeCoding, a GenAI-assisted prototyping method, cutting proof-of-concept development time by 60% and accelerating innovation cycles across units. - Partnered with Microsoft and AWS to design and execute enterprise rollouts of Copilot and Amazon Q, building adoption playbooks and champion programs. - Led pilots integrating ChatGPT Enterprise, Claude, and MCP infrastructure to automate QA workflows, expand AI-assisted knowledge creation, and improve test coverage. - Delivered keynote sessions at the Volaris Quadrant Conference and Virtual AI Summit, training leaders from 40+ business units on AI champion programs, adoption roadmaps, and governance best practices. - Built internal knowledge-sharing communities through Viva Engage and advisory forums, enabling repeatable, standardized AI adoption across the Volaris portfolio.

  • Angel Investor at Foodie Thought LLC
    2022 - Present · 4 yrs 6 mos

    - Strategic Investment & Support - Serve as the investor for Foodie Thought LLC, a company dedicated to empowering local artists, children's book authors, and musicians to publish their art and music using cutting-edge technology. - AI-Driven Empowerment - Utilize AI and advanced technologies to support creators in achieving their goals, helping them reach broader audiences and realize their dreams. - Collaboration with Creatives - Work closely with artists and authors, providing resources and guidance to bring their creative visions to life through innovative publishing and distribution channels. - Technological Innovation - Lead efforts to integrate AI into the creative process, enabling more efficient production, marketing, and distribution of content across various platforms. - Community Building - Foster a supportive environment that nurtures creativity and collaboration, helping individuals grow and succeed in their respective fields.

  • Managing Partner at Gems Peridot Fund LLC
    May 2021 - Present · 5 yrs 2 mos

    - Strategic Leadership - Established and lead Gems Peridot Fund LLC, a forward-thinking real estate investment firm specializing in short-term vacation rentals in the Pacific Northwest. - AI-Driven Investments - Leveraged AI and advanced data analytics to identify and capitalize on hidden investment opportunities, leading to significant portfolio growth and strong ROI. - Operational Excellence - Oversee property acquisitions, market analysis, and the implementation of cutting-edge technology to maximize occupancy rates and customer satisfaction. - Innovation & Growth - Continuously explore and adopt new technologies to stay ahead in the competitive market, ensuring the firm’s offerings are both unique and profitable.

  • Director Customer Support at CipherHealth
    Nov 2021 - Jan 2023 · 1 yr 3 mos

    - Restructured support operations from a flat model to a tiered structure with defined SLAs and specialized roles, cutting backlog by 54% (from ~1,200 to <550 cases) within 10 months. - Designed and launched a Technical Account Manager (TAM) program delivering white-glove service for enterprise accounts, driving a 20% CSAT increase and deeper executive engagement. - Built a self-service portal in 6 months, integrating knowledge base, FAQs, and guided workflows; reduced inbound case volume by 18% and improved first-contact resolution. - Partnered with a Philippines-based BPO to expand inbound phone coverage, ensuring SLA adherence, quality monitoring, and seamless Tier 1–Tier 2 handoffs. - Led incident and escalation management for top-tier accounts, delivering real-time coordination, executive-ready RCAs, and restoring customer trust during critical events. - Authored a Support Operations Handbook and rolled out performance KPIs (FRT, TTR, FCR), creating consistent processes and accountability across the team. - Directed 50+ cross-functional initiatives with Product, Engineering, and Customer Success to reduce escalations, accelerate feature adoption, and strengthen retention in strategic accounts.