Hire the Best Content Production Freelancers in Chicago, IL

I work with small business owners and marketing teams who know AI should be doing more for them — but can't figure out where to start, what to build, or whether what they've tried is actually working. That's where I come in. My engagements start with structured discovery: understanding how the business operates, where time and money are leaking, and what the actual goal is before anyone touches a tool. From there I scope the work, draft the SOW, and either lead the build or coach the team through it — depending on what the business actually needs. Coaching & AI Adoption A significant part of my practice is working directly with business owners and their teams on AI adoption. Not generic tool tutorials — structured, personalized sessions built around your business, your workflow, and your specific gaps. Some clients come in knowing nothing. Some have tried a handful of tools and gotten nowhere. Either way, we start where you are and build from there. Sessions run as standalone engagements or as an ongoing retainer, and I've developed curriculum for both individual owners and small teams making the shift to AI-assisted operations. Consulting, Systems & Implementation On the consulting and systems side, I diagnose operational pain points and design purpose-built AI solutions — financial dashboards, CRM pipelines, workflow automation, knowledge bases — engineered for the client's specific constraints, typically at zero infrastructure cost. On the content and strategy side, I architect generative AI production systems that replace traditional agency overhead: full multi-platform content operations running on lean AI stacks, with the metrics to show it. Recent work: a complete operational suite for a professional motorsport racing team (financial command center with live budget tracking, AI document intelligence, and a full sponsor pipeline CRM — two zero-infrastructure web apps, single sprint); a fully AI-produced weekly podcast now at Episode 30, growing 20% month-over-month; and an internal AI workflow transformation that replaced an 8-person freelancer team and documented over $200K in annual overhead reduction. Certified: AI Prompt Engineering & Advanced Data Analytics — Vanderbilt University (via Coursera) If you're past the tool-dabbling stage and ready to build something that actually runs — or just need someone to sit down and make sense of all of it with you — let's talk. Expertise/Skills section: AI Strategy & Implementation Consulting Discovery, Scoping & SOW Development AI Workflow Architecture & Automation AI Coaching & Adoption Training Generative AI Tech Stack Evaluation Multi-Platform Content Strategy Business Process Analysis & Optimization LLM Integration & Knowledge Base Design Content Performance Analytics SMB Operations & Systems Design

👋🏽 Hi, my name is Thomas, and I am a graphic designer with over 19 years of experience in design and creative strategy, based in the Chicagoland area. My journey in the creative field began with earning my Bachelor’s Degree from The Illinois Institute of Art, Chicago, where I cultivated a passion for blending artistic vision with strategic intent. To deepen my expertise, I completed the Marketing Strategy Certificate Program through Cornell University’s online division, gaining MBA-level strategic marketing training that has sharpened my ability to craft campaigns that drive results. I’ve also kept pace with evolving digital trends through the Web Design and Development Certificate Program at Florida State University, ensuring my work remains innovative and user-focused. Additionally, I hold a Google Ads Display Certification, equipping me with the tools to create impactful digital advertising strategies. Throughout my career, I’ve excelled as both an in-house creative lead and a dedicated freelancer, collaborating with clients for over a decade to achieve their unique design goals. Whether I’m leading a team, building a campaign, or diving into hands-on design work, my focus is always on delivering solutions that stand out and connect with audiences. As a seasoned creative professional, I bring a unique blend of skills to the table, including: • Creative Vision: Developing compelling concepts that align with brand objectives and captivate audiences. • Leadership: Mentoring teams and fostering a collaborative environment to achieve outstanding creative results. • Strategic Thinking: Aligning creative initiatives with business goals to deliver measurable success. • Communication: Articulating ideas effectively to stakeholders and building consensus around innovative solutions. • Brand Management: Ensuring consistent brand identity across all platforms and campaigns. • Project Management: Managing multiple projects simultaneously while meeting deadlines and quality expectations. • Adaptability: Thriving in fast-paced environments and pivoting strategies as needed. • Technical Proficiency: Leveraging tools like Adobe Creative Suite, video production software, and digital platforms to execute creative projects. • Problem-Solving: Tackling challenges with innovative and practical solutions. • Trend Awareness: Staying ahead of industry trends to produce work that resonates with contemporary audiences. I’m always open to discussing creative opportunities or sharing insights—feel free to connect!

Hi there, I'm Anna! A professional writer and copy editor for over 7 years, and video editor for 6 years, I am excited to help with your needs. My portfolio ranges from short-form creative projects like 'Letters from Santa' to SEO-driven articles, profiles, and newsletters. A frequent ghostwriter, I, unfortunately, cannot share all of my favorite pieces, but you can find much of my recent work on Sandiego.com, OHSCanada.com, A-Z Animals, and Choosing Nutrition. In addition to writing, I often edit existing blog pieces and articles to have higher-ranking SEO attributes while ensuring they flow and keep readers engaged. I've worked with short-form videos like Reels and TikToks, as well as travel vlogs, podcast cuts, and even full-length documentaries. You can find examples of my work on my website under 'Contract Work' or on my UpWork portfolio. I look forward to working with you!