Product Lead, Systems & AI (Tampa)

Product Lead, Systems & AI — The Hotel Guy (THG)Location: Tampa, FL (In-person, initial 1-month engagement)Compensation (Contract): $2,500–$3,000/week to Potential Full Time Salaried PositionOverviewThe 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 StructureThis role begins as a 1-month, in-person engagement in Tampa focused on:Gaining deep operational contextAnalyzing and refining existing workflowsProducing a clear, actionable systems and product roadmapSuccessful execution can transition into a long-term leadership role developing and managing internal products and operations.The RoleThis 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:1. Analyze — Understand how the business operates today2. Structure — Translate workflows into clear, scalable systems3. Execute (or Spec for Build) — Define what gets built, improved, or automatedThis role requires clarity of thinking, strong judgment, and the ability to operate without heavy structure.What You'll DoAnalyze and refine workflows across:Client intake and scopingHotel sourcing and negotiationBooking and coordinationBilling and financial controlsClient communication and reportingIdentify opportunities to:Increase efficiency and speedReduce operational risk and errorImprove visibility across jobs and financialsTranslate findings into:Process maps and workflow diagramsProduct requirement documents (PRDs)System logic and user flowsA prioritized roadmap of initiativesDefine:Where existing tools can be leveragedWhere custom solutions are warrantedHow systems should support both human expertise and automationEnsure systems and workflows are designed with appropriate consideration for data security, privacy, and operational controlLeverage AI-assisted tools to prototype, refine, and accelerate system developmentEstablish the foundation for scalable internal infrastructure and future product developmentWho You Are6–8+ years experience in product, operations, business analysis, or a hybrid roleProven ability to solve complex operational problems and structure ambiguous systemsComfortable working directly with leadership and extracting insight from unstructured environmentsStrong systems thinker — you understand how processes connect end-to-endDetail-oriented, but pragmatic in prioritization and executionOperates with independence, speed, and sound judgmentComfortable using AI-assisted tools (e.g., Claude, Cursor, or similar) as a core part of how you think, prototype, and buildStrong awareness of data sensitivity, privacy, and intellectual property, with the judgment to design systems that protect both client and company interestsIdeal BackgroundProduct Manager (especially internal tools or ops-heavy environments)BizOps / Strategy roles in fast-moving companiesFounder's Associate or early-stage operatorExperience working closely with non-technical foundersNice to HaveExposure to travel, hospitality, entertainment production, or music toursFamiliarity with tools like Airtable, Notion, or similar platformsExperience with AI-assisted development workflowsExperience designing systems that integrate with CRM platforms (e.g., Salesforce)What Success Looks Like (First 30 Days)Clear, structured view of core business workflowsIdentification of the highest-leverage opportunities for improvementA prioritized roadmap for system and product developmentInitial specs that can be executed by developersWhat This Role BecomesLead development of internal systems and operational infrastructureLeadership over product direction for internal (and potentially client-facing) toolsA central role in scaling a high-performance business into its next phaseFinal NoteThis 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.