Wesley Cunningham

Logistics & Transportation (20+ yrs) | Startup Operations | Payments & Financial Ops | Automation & AI Workflows (LLMs, Zapier, Make) | Global Travel Logistics

Maryville, Tennessee, United States

About

Operations professional with 20+ years of experience in logistics, transportation, and supply chain operations, combined with recent hands-on experience working inside a fast-moving startup environment. My background spans trucking, air freight, and ocean logistics, where I developed deep expertise in operational execution, carrier relationships, and global supply chain workflows. Throughout my career I’ve focused on improving operational efficiency, solving complex process issues, and building strong partnerships across teams and vendors. At TrueNorth, a logistics technology startup, my role expanded beyond traditional operations into payments operations, platform operations, and cross-functional collaboration with product and marketing teams. Working in a startup environment required adaptability and systems thinking, contributing across multiple areas to support platform growth. Alongside operational work, I’ve developed a strong interest in automation and emerging technologies. I have built and experimented with internal workflows using AI and automation tools, including LLM-based knowledge systems, webhook integrations, and no-code automation platforms such as Zapier and Make to streamline processes and improve operational efficiency. I also bring hands-on experience with web platforms, contributing to website development, landing pages, and CMS management using Webflow. Core areas of expertise - Operations Management - Startup Operations - Logistics & Transportation - Payments & Financial Operations - Process Optimization - Automation & Workflow Systems - AI / LLM Knowledge Systems (RAG, SQLite) - Zapier / Make Automation - Webflow & Digital Platforms - Cross-functional Collaboration I hold a degree in International Business with a minor in German and maintain a strong interest in global trade, operational systems, and emerging technologies that improve how companies operat

Experience

  • Managing Director at Cultural Expressions Group
    Nov 2018 - Present · 7 yrs 9 mos

    ● Increase the yearly revenue by expanding the targeted ad spending, creating email funnels, developing targeted marketing campaigns via Google and Facebook, training customer service representatives, and administering an active social media page. ● Negotiate and approve 18+ agreements with suppliers and distributors and save 10-15% with multiple suppliers with product volume discounts. ● Manage an international distribution team of seven. ● Establish the online presence for brands via Google Ads and remarketing. ● Increase website traffic by 126% through the implementation of effective sales strategies. ● Develop and manage 18 supplier accounts. ● Generate a 160% growth in revenue and ROAS of nearly ten by maintaining an agile and responsible organization, monitoring industry forecasts, increasing Google/Bing Ads budgets by 300%+ and Facebook by 200%+, and adjusting marketing strategies. ● Strategize solutions and enhance business operations by capitalizing on industry and marketplace trends. ● Maximize the outreach and sales of products by building, implementing, and improving initiatives using Google Display Ads and strategic remarketing ads on Facebook. ● Develop the company's brand, vendor relations, and marketing strategies. ● Design, implement and monitor 500+ product pages and three websites, as well as SEO tools. ● Create the site layout and user interface utilizing HTML and CSS. ● Strengthen the company's brand and identity by creating a distinctive website and logo. ● Implement successful Google campaigns and SEO for various types of company websites in alignment with markets.

  • International Travel Planning & Regional Operations Exposure at WorldWideyedWes
    Jan 2022 - Present · 4 yrs 7 mos

    Extensive independent international travel with a focus on multi-country itinerary planning, travel logistics, and regional familiarity across multiple continents. • Traveled to 10+ countries over the past two years, managing complex multi-country travel planning and logistics • Logged over 20,000 miles annually coordinating flights, accommodations, and regional transportation • Lived in Guadalajara, Mexico for four years, gaining deep familiarity with regional infrastructure and travel coordination • Completed extended stays in Kuala Lumpur, Malaysia, with additional travel across Argentina and India • Managed all booking, visa requirements, entry documentation, and itinerary coordination independently • Coordinated flights, accommodations, and regional transportation using multiple booking platforms and airline systems • Developed strong familiarity with international travel operations, regional transportation networks, and cultural business environments This experience strengthened my ability to plan complex travel logistics and adapt to new operational environments.

  • Operational Specialist at TrueNorth - Profits to Truckers
    Jun 2022 - Jan 2026 · 3 yrs 8 mos

    Operations | TrueNorth Joined TrueNorth supporting carrier payouts in a fast-growing logistics technology startup (~30 employees). As the company evolved, my role expanded across payments operations, platform operations, product collaboration, and growth initiatives. Payments & Financial Operations • Managed carrier payment workflows including ACH and wire payouts • Investigated payment discrepancies and coordinated resolutions with banking partners and internal teams • Performed reconciliation and maintained accurate payment records • Assisted with monitoring operational credit card expenditures Operations & Process Improvement • Helped develop internal workflows and operational documentation to support scaling • Worked cross-functionally with product, support, and finance teams to resolve operational issues • Identified opportunities to improve internal processes and operational efficiency Product & Platform Collaboration • Provided operational insights from carrier interactions to support product development • Contributed feedback supporting platform features including AI-powered tools and improved carrier workflows • Assisted with rollout and adoption of new platform capabilities Web & Marketing Support • Assisted with Webflow website updates, landing pages, and messaging improvements • Contributed to feature launches, social campaigns, and product announcements Automation & AI Systems • Built automation workflows using Zapier and Make • Implemented webhook integrations to streamline internal processes • Implemented LLM-based knowledge systems (RAG / SQLite) for internal documentation and knowledge access Worked across operations, product, and growth initiatives in a fast-paced startup environment requiring adaptability and rapid learning.

  • Partner/Logistics Specialist at EQUITONE USA
    Mar 2019 - Jun 2022 · 3 yrs 4 mos

    ● Supervise all aspects of the order fulfillment process from sales order to invoice in SAP, including the entry of the customer PO, coordination of the movement of goods, management of customer delivery expectations, and preparation of reports. ● Manage day-to-day shipments globally and domestically, including 30+ daily containers daily to various locations in the USA from Europe, and approve rates with the freight forwarder. ● Optimize shipment process and customer satisfaction utilizing best modes of movement. ● Coordinate with the Etex offices in Europe on the annual purchase and movement of goods. ● Forecast loads, optimize routings and reduce the delivery time to West Coast by over two weeks by building and maintaining relationships with internal offices and external partners. Increase load averages and decrease lead times by around a week on average by executing real-time decisions on routing. ● Ensure trade compliance with proper export/import documentation and custom filings. ● Manage the communication with customers on scheduling and project deadlines and provide customer support by helping seven customers with product and technical questions. ● Expand visibility to customers by preparing weekly order reports and projected arrival dates. ● Provide support to the sales team and senior leadership with the decision-making process and management of logistical expectations based on market conditions by preparing quarterly updates on the supply chain issues. ● Lead the testing and structuring of web portal in the USA and deliver actionable feedback to the development team in Europe to identify areas of improvement.

  • Transportation Associate at Averitt Express
    Jul 2009 - Nov 2018 · 9 yrs 5 mos

    ● Drove tractor-trailer and ensure goods are transported to service centers and customers in an efficient, timely manner. ● Retained high standards of customer service and professionalism, acting as the face of the company. ● Received full training as dock supervisor.