GTM engineer vacation rental platform

OnSeason builds distribution infrastructure for the vacation rental industry. Its API powers distribution for travel tech companies, and its AI-powered website builder helps vacation rental companies launch direct booking websites without code.

Own outbound sales from prospecting through closing deals Build repeatable acquisition systems using AI, automation, and data enrichment Run cold calls, personalized email campaigns, Linked In outreach, and other prospecting activities Sell the AI channel manager and AI website builder to property managers Test channels, messaging, segments, and workflows; scale what converts and stop what does not Work with the founders and product team, bring customer feedback into the product, and help shape the GTM strategy Build an AI-powered prospecting engine, automate repetitive work, connect tools and APIs, and use agents to improve productivity

Hands-on experience in B2B outbound sales, growth, business development, or a similar role Comfortable with cold calling, running demos, negotiating, and asking for the sale Understand lead sourcing, enrichment, segmentation, email deliverability, Linked In sequences, and CRM hygiene Experience building workflows or agents with AI and automation Able to work with APIs, webhooks, no-code tools, and data Excellent written and spoken English Focus on measurable outcomes, including qualified conversations, onboarded property managers, and paying customers Take ownership, move fast, and work independently Not a fit for candidates who rely on generic emails, are uncomfortable with cold calls or rejection, need daily task lists or established processes, talk about AI without using it, or prioritize elaborate workflows over acquiring customers Not a fit for candidates looking for a strictly 9-to-5 Будет плюсом: experience in hospitality, vacation rentals, travel tech, or property management software;

experience creating a playbook at an early-stage startup;
Spanish

Base salary plus unlimited performance-based upside ESOP after month 6, depending on performance and team fit