H. Michael Wayland
Director of Digital Strategy @The 20 Msp - Your Managed It Department
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WORK HISTORY
Director of Digital Strategy @The 20 Msp - Your Managed It Department
Bentonville, AR, US
Strategic Leadership in AI-Driven Digital Innovation:As Director of Digital Strategy, I lead initiatives that blend web development, automation, and other online and digital services, with cutting-edge AI automation to drive digital transformation. I focus on designing scalable, intelligent systems that streamline internal workflows, enhance client retention, and create measurable value across our org and partners.AI & Automation Initiatives:• Designed and implemented AI-powered content and design pipelines using Claude, Gemini, ChatGPT and other integrated tools, enabling automated workflows.• Architected and developed internal automation tools and workflows, using AI, databases, and other integrated tools to support team and provide integrated low-cost, high-performance solutions.• Architected internal semi-autonomous and Human in the Loop (HITL) AI agents and agentic systems used for internal and real-world use cases that created measurable and billable deliverables to clients.• Integrated AI-driven SOP generation and documentation processes to streamline MSP operations and reduce manual overhead.Web Strategy & Infrastructure:• Founded and scaled the Web Services division at The 20 MSP, growing from zero to 100+ managed websites.• Directed development of websites emphasizing brand alignment for clients ranging from small businesses to national and national consumer brands like Colace and Betadine.• Oversaw security and compliance for WordPress and other web infrastructure, including custom plugin development, site hardening, and system automation.Digital Transformation & Client Success:• Partnered closely with MSP owners and enterprise clients to align technical execution with business strategy.• Delivered measurable performance improvements and marketing ROI through design, SEO, and backend process optimization.• Translated technical complexity into client-first strategies that scale efficiently while preserving quality and vision.
EDUCATION
University of Houston, C.T. Bauer College of Business
BBA, Marketing
University of Houston, C.T. Bauer College of Business
Bachelors of Business Administration, Marketing
Lamar University
Masters Business Administration, Enterprise Resource Planning
SKILLS
ABOUT H. MICHAEL WAYLAND
We’ve got IT Covered. I’m a technical, business, and workflow automation consultor and implementor. Founder of Byte-Werx, a cutting-edge managed service provider focused on removing IT friction and issues to help technology become an asset and help your business grow faster that was acquired in October 2022 by The 20 MSP. I joined The 20 MSP as a Director of Marketing Operations to create internal new revenue initiatives and departments, starting with a Managed Website Agency, EasyIT4U (a soloprenuer and micro business IT Service product for 1-5 users), and work as The 20 MSPs point person for our Microsoft partnership.The 20 MSP provides businesses with 100% true FLAT Rate IT Support with a nationwide footprint. Unlike every other Outsourced IT Support or Managed IT Services company, we take on all the risk so you can focus on your business, not your IT problems.Working with The 20 MSP not only ensures responsive and reliable IT support and IT management, but it also removes unpredictable fluctuations to IT spending. We have a strong, long term relationship mentality and utilize our expertise and experience to increase productivity and maximize profitability. Learn more about our services or work with us here:
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