Product Lead, Systems & AI

Product Lead, Systems & AI — The Hotel Guy (THG) Compensation (Contract): $2,500–$3,000/week to Potential Full Time Salaried Position Location Tampa, FL (In-person, initial 1-month engagement) Overview The Hotel Guy (THG) is a high-performance travel company specializing in group and production travel for ad agencies, entertainment companies, music tours, and Fortune 500 brands. We operate in environments where speed, precision, and relationships directly impact outcomes — and consistently deliver at a level that outperforms traditional agencies. As we continue to scale, we are investing in the evolution of our internal systems and workflows to increase efficiency, visibility, and leverage across the business. We are looking for a senior operator who can help shape that next phase. Engagement Structure This role begins as a 1-month, in-person engagement in Tampa focused on: Gaining deep operational context Analyzing and refining existing workflows Producing a clear, actionable systems and product roadmap Successful execution can transition into a long-term leadership role developing and managing internal products and operations. The Role This position sits at the intersection of product, systems, business operations, and AI. You will work directly with the founder and core team to understand how the business operates across sales, negotiation, booking, billing, and client delivery — and translate that into structured systems, workflows, and product-ready specifications. Think in phases: Analyze — Understand how the business operates today Structure — Translate workflows into clear, scalable systems Execute (or Spec for Build) — Define what gets built, improved, or automated This role requires clarity of thinking, strong judgment, and the ability to operate without heavy structure. What You’ll Do Analyze and refine workflows across: Client intake and scoping Hotel sourcing and negotiation Booking and coordination Billing and financial controls Client communication and reporting Identify opportunities to: Increase efficiency and speed Reduce operational risk and error Improve visibility across jobs and financials Translate findings into: Process maps and workflow diagrams Product requirement documents (PRDs) System logic and user flows A prioritized roadmap of initiatives Define: Where existing tools can be leveraged Where custom solutions are warranted How systems should support both human expertise and automation Ensure systems and workflows are designed with appropriate consideration for data security, privacy, and operational control. Leverage AI‑assisted tools to prototype, refine, and accelerate system development. Establish the foundation for scalable internal infrastructure and future product development. Who You Are 6–8+ years experience in product, operations, business analysis, or a hybrid role Proven ability to solve complex operational problems and structure ambiguous systems Comfortable working directly with leadership and extracting insight from unstructured environments Strong systems thinker — you understand how processes connect end‑to‑end Detail‑oriented, but pragmatic in prioritization and execution Operates with independence, speed, and sound judgment Comfortable using AI‑assisted tools (e.g., Claude, Cursor, or similar) as a core part of how you think, prototype, and build Strong awareness of data sensitivity, privacy, and intellectual property, with the judgment to design systems that protect both client and company interests Ideal Background Product Manager (especially internal tools or ops‑heavy environments) BizOps / Strategy roles in fast‑moving companies Founder’s Associate or early‑stage operator Experience working closely with non‑technical founders Nice to Have Exposure to travel, hospitality, entertainment production, or music tours Familiarity with tools like Airtable, Notion, or similar platforms Experience with AI‑assisted development workflows Experience designing systems that integrate with CRM platforms (e.g., Salesforce) What Success Looks Like (First 30 Days) Clear, structured view of core business workflows Identification of the highest‑leverage opportunities for improvement A prioritized roadmap for system and product development Initial specs that can be executed by developers What This Role Becomes Lead development of internal systems and operational infrastructure Leadership over product direction for internal (and potentially client‑facing) tools A central role in scaling a high‑performance business into its next phase Final Note This role is designed for someone who can quickly understand a complex business, impose structure where needed, and make high‑quality decisions about what to build and what to leave alone. If you operate well in that environment, this is a rare opportunity to have meaningful involvement in how a business scales. #J-18808-Ljbffr The Hotel Guy