Go-to-Market
Founding GTM Engineer
- Sofia, Bulgaria
- Hybrid or Remote
- Full-time
Own supply-side GTM: bring property managers onto the network and convert them into paying website builder customers.
Apply for this roleAbout the role
OnSeason is building the distribution infrastructure for the vacation rental industry. Our API powers distribution for 40+ travel tech companies — from Y Combinator startups to established OTAs. Our PMS partners include Guesty, Apaleo, Mews, Oracle's Opera, and 35+ others.
Our latest product brings that same infrastructure directly to property managers: an AI-powered website builder that lets vacation rental companies launch high-converting direct booking websites without writing a single line of code.
We're a small, product-obsessed team based in Sofia, backed by Eleven Ventures, operating at the intersection of hospitality, technology, and AI. We're looking for a GTM Engineer to help us grow the supply side of our business: bring more property managers onto our distribution network and turn as many of them as possible into paying customers of our website builder.
What you will actually do
- 01
Own outbound from start to finish. Find prospects, reach decision-makers, book demos, run conversations, handle objections, and close deals.
- 02
Build repeatable acquisition systems. Use AI, automation, and data enrichment to identify, qualify, and reach thousands of relevant property managers.
- 03
Pick up the phone. Run cold calls, personalized email campaigns, LinkedIn outreach, and whatever else gets you in front of the right people.
- 04
Sell two compelling propositions. Help property managers distribute their inventory through our upcoming AI channel manager and adopt our AI website builder to grow direct bookings.
- 05
Experiment constantly. Test new channels, messaging, segments, and workflows. Double down on what converts and kill what doesn't — fast.
- 06
Work directly with the founders and product team. Bring customer feedback into the product and help shape our GTM strategy.
How we work with AI
We're an AI-native company. We use AI across engineering, product, and operations, and expect the same from GTM.
We don't want someone who simply prompts Claude to write cold emails. We want someone who can build an AI-powered prospecting engine, automate repetitive work, connect tools and APIs, and use agents to accomplish what traditionally required an entire sales team.
The specific tools you use matter less than your ability to figure things out and make them work together.
AI should make you dramatically more productive, not replace your judgment or your willingness to talk to customers.
You will fit if
You have hands-on experience in B2B outbound sales, growth, business development, or a similar role.
You're comfortable cold calling strangers, running demos, negotiating, and asking for the sale.
You understand modern outbound: lead sourcing, enrichment, segmentation, email deliverability, LinkedIn sequences, and CRM hygiene.
You're genuinely obsessed with AI and automation. You've already built workflows or agents that make you more effective.
You're technical enough to work with APIs, webhooks, no-code tools, and data. You don't need to be a software engineer, but you should think like a builder.
You have excellent written and spoken English. Spanish is a major advantage.
You care about measurable outcomes: qualified conversations, onboarded property managers, and paying customers.
You take ownership, move fast, and figure things out without someone telling you what to do next.
You will not fit if
You think sales means sending 100 generic emails and waiting for replies.
You're uncomfortable picking up the phone or dealing with rejection.
You need a manager to give you a daily task list.
You talk about AI more than you actually use it.
You prefer building elaborate workflows over getting real customers.
You're looking for a strictly 9-to-5.
You need established processes, playbooks, and layers of management to succeed.
Nice to have
You have experience in hospitality, vacation rentals, travel tech, or property management software.
You've worked in an early-stage startup where you had to create your own playbook.
Why join us
Real ownership: build and own an important part of our supply-side GTM engine from the ground up.
Two growth opportunities: help scale a global accommodation distribution network with partners like Muse, Instinct and Grok Bot, while selling a new AI-native SaaS product.
AI-first environment: work with a team that actively builds and ships with AI every day.
Direct founder access: work closely with the founders, influence product decisions, and see the immediate impact of your work.
Performance-based compensation: base salary plus unlimited performance-based upside.
ESOP: after month 6, depending on performance and team fit.
We're not looking for someone to manage a sales process. We're looking for someone to build one, automate what can be automated, and personally close the deals that matter.