Lee Dickson
Director of Sales and Operations at raia AI
Bradenton, Florida, United States
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Lee Dickson is the Director of Sales & Operations at raia AI, where he helps software and technology companies deploy practical AI solutions that drive measurable operational and revenue growth. As part of the founding team behind raia, Lee has played a key role in building an enterprise AI agent platform designed specifically for organizations looking to integrate AI across sales, support, marketing, engineering, and operational workflows. His work focuses on helping companies move beyond isolated AI experiments and toward scalable, secure, and productized AI ecosystems that create long-term competitive advantages.
Lee is also the co-host of The AI Guys, a technology podcast and learning community with more than 500,000 subscribers focused on making artificial intelligence approachable and actionable for business leaders. Through his work with executives and operating groups across organizations ranging from $5M to $500M+ in annual recurring revenue, he has become a recognized voice on practical AI adoption, operational AI strategy, and how companies can safely deploy agentic systems that empower teams while maintaining ownership, governance, and scalability.
With 9+ years experience in AI enablement and growth strategy, Lee has worked closely with SMBs and enterprise organizations to modernize customer engagement, streamline operations, and accelerate digital transformation initiatives. Through raia, he has helped organizations deploy customizable AI agents capable of handling everything from customer support automation and AI SDR workflows to code modernization, reporting automation, and embedded AI experiences inside SaaS products across industries including software, healthcare, financial services, real estate, automotive, travel, and hospitality.
Area of Expertise
Topics
The Agentic Advantage - Building AI Agents That Solve Real Problems
AI isn't the future - it's already reshaping how businesses operate, sell, and support. But while everyone’s talking about LLMs and automation, most companies still struggle to go from “cool idea” to real results. In this session, Lee Dickson - founding team member of raia AI and host of The AI Guys Podcast (500k+ YouTube subscribers) - breaks down how SMBs and enterprises are successfully deploying customizable AI agents that drive revenue, reduce operational drag, and improve customer experience.
You’ll learn the blueprint for low-to-no code AI deployment, how to match agents to business needs (like sales, support, and marketing), and what it really takes to scale AI in your organization - without hiring a team of data scientists. Whether you’re a tech leader, operator, or simply tired of AI hype with no substance, this talk will equip you to build smarter, faster, and with purpose.
Session Outline:
1. The Real State of AI in Business (2026) – hype vs. reality
2. What Makes an AI Agent Actually Useful?
3. The 3 Pillars of Smart Deployment – speed, simplicity, scalability
4. Case Studies – real companies using AI agents in sales, support, ops
5. Avoiding Common Mistakes in AI Rollouts
6. Your AI Blueprint – how to deploy an agent in 30 days or less
7. Closing Thoughts – building your agentic workforce
Ask Us Anything: Building Real-World AI Agents for Business
Format:
Fireside Chat / AMA Panel (30-60 mins)
Hosted by Lee Dickson & Rich Swier (co-host of The AI Guys)
Abstract:
You’ve seen the hype. Now let’s get practical. In this live AMA-style session, Lee Dickson and Rich Swier - co-hosts of The AI Guys podcast (500k+ YouTube subscribers) and builders of raia AI - open the floor to the questions business leaders, operators, and tech pros are really asking about AI.
From deployment timelines to hallucination prevention, ethics to employee augmentation - nothing’s off limits. Whether you’re planning your first AI rollout or scaling from one use case to a dozen, this is your chance to get direct insights from AI practitioners who’ve helped companies from $5M startups to $500M enterprises make AI work.
Topics we’ll cover (based on audience Q&A):
- How to scope AI roles in your org
- Getting buy-in from teams
- Tools, models & platforms that scale
- Budgeting and measuring ROI
- Common pitfalls to avoid
- Future-proofing your AI stack
Bonus:
Bring your current challenge - we may workshop it live.
AI at the Heart of Healthcare: Transforming Engagement, Operations, and Care
Healthcare providers face increasing pressure to deliver exceptional patient experiences while managing rising operational complexity. AI-powered digital assistants are emerging as a game-changing solution, enabling practices to streamline workflows, reduce administrative burdens, and focus more on patient care.
In this session, Lee Dickson - founding team member of raia AI and host of The AI Guys podcast (500k+ subscribers on YouTube) shares real-world examples of how their current healthcare and patient service providers are adopting AI solutions to improve care delivery. Attendees will learn how customizable AI agents can:
- Automate scheduling, intake, and billing processes
- Enhance patient engagement with personalized, conversational support
- Support medical staff with faster access to information and documentation
- Drive measurable cost savings while increasing patient satisfaction
Through case studies and best practices, this session will demonstrate how providers can confidently adopt AI to transform both front-office operations and clinical workflows. Attendees will leave with practical insights to begin building their own AI adoption roadmap - positioning their organizations to thrive in a rapidly evolving healthcare landscape.
DataWeek 2025 Sessionize Event
Lee Dickson
Director of Sales and Operations at raia AI
Bradenton, Florida, United States
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