IT Specialist

IT Specialist – Beachside Vacation Rentals Full-time | Remote (Latin America) Reports to: CTO Compensation: USD $2,000–$2,500 / month About Beachside Vacation Rentals Beachside Vacation Rentals is a performance-driven, technology-forward hospitality company managing a growing portfolio of short-term rental properties along Florida's Space Coast. Our focus is to deliver a consistent, high-quality guest experience while protecting owner assets and optimizing revenue through disciplined operations and smart use of technology. We operate with high standards, strong accountability, and a commitment to operational excellence across all departments, leveraging modern systems and automation to drive efficiency, consistency, and scalability. The Role The IT Specialist owns day-to-day technology and integrations for Beachside, working closely with our CTO. You're the team's go-to for tech issues as they come up, the owner of our software vendor relationships, and the builder behind the tools and automations that make the company run more efficiently. This is a hands-on role for someone who reaches for AI and automation by default, solves problems end to end, and would rather build a tool than file a request for one. What You'll Do Serve as the primary point of contact for day-to-day IT and tech issues across our small remote team — troubleshoot, unblock people, and keep things running. Manage software vendor relationships — open, track, follow up on, and escalate support tickets with SaaS providers until issues are fully resolved. Design and build tools, automations, and internal dashboards (no-code/low-code platforms, scripts) that improve how the company operates. Connect systems using APIs, webhooks, and automation platforms (Zapier/Make-style) to build lightweight internal tools. Support and maintain our core tech stack, including Guesty, Conduit, Airtable, Klaviyo, Google Tag Manager, and Vercel. Use AI tools daily as a core part of how you work — to move faster, automate the repetitive, and build smarter. Partner with the CTO on technology and integration projects. Keep clear documentation of systems, logins, and processes as you go. What We're Tracking Fast resolution of day-to-day tech issues and team blockers Vendor support tickets tracked, followed up, and resolved Tools and automations shipped that save the team time Reliability and uptime of core systems and integrations Clear, current documentation of systems and processes Who You Are Highly proficient with AI tools (Claude, ChatGPT, Perplexity, etc.) — you use them daily as a core part of how you work, not just casually. Able to independently design and build your own tools and automations (no-code/low-code, scripts, internal dashboards) rather than just requesting them from a developer. Comfortable being the go-to for day-to-day IT/tech across a small remote team. Experienced managing vendor relationships — opening support tickets, following up, and escalating until resolved. Comfortable with basic scripting and APIs (Python, JavaScript, webhooks, Zapier/Make-style automation) — enough to connect systems and build lightweight tools. Understand, or can quickly learn, how the short-term rental / vacation rental management business operates. Self-directed and resourceful — you own problems end to end with minimal oversight. A strong written communicator who can explain technical things clearly to non-technical teammates and vendors. Organized and detail-oriented — you document systems, logins, and processes as you go. Fluent, professional English (written and spoken). Able to overlap with US business hours to support the team. Nice to Have Familiarity with our core stack — Guesty (PMS), Conduit, Airtable, Klaviyo, Google Tag Manager, Vercel — or comparable tools. Prior experience at a property management company, PMS/proptech company, or STR-adjacent business. Experience with marketing/CRM tools (Klaviyo, GoHighLevel) and basic analytics (GTM/GA). Experience with database/spreadsheet-heavy operations tooling (Airtable in particular). What We Offer Fully remote work from your home. Direct collaboration with the CTO and real ownership of tech, integrations, and automation. A technology-forward company that wants you building, not just ticketing. Room to grow as Beachside scales. Compensation USD $2,000–$2,500 / month Reports To: CTO, Beachside Vacation Rentals