More than 200,000 properties in over 45 countries already automate their check-in with Chekin. Now we're growing in Portugal and Italy, two of Europe's biggest tourism markets, and we're looking for someone to lead that growth from the first call to the signed contract.

About ChekinChekin automates check-in for hotels and vacation rentals. We take care of guest registration and ID verification, mandatory reporting to the authorities .online payments and deposits, remote access, upselling and tourist tax. We were founded in Seville in 2018.

Your missionIn Portugal, every accommodation is legally required to register its guests, and many still do it by hand. Your mission is to turn that pain point into new customers. You'll run the full sales cycle with property owners, vacation rental managers and hotels, and help build our commercial presence in both markets.

What you'll do

- Own the full sales cycle: inbound lead qualification, discovery, demo, proposal, negotiation and close.
- Build your own pipeline through outbound prospecting (calls, email, LinkedIn) in Portugal and Italy.
- Run tailored demos for each type of customer: individual owners, property managers with dozens of units and hotel groups.
- Explain local regulations (guest registration, tourist tax) and turn them into a value argument.
- Work with Marketing and Partnerships on campaigns, webinars and alliances with local PMS providers and industry associations.
- Keep your pipeline and forecast up to date in HubSpot, and hit your monthly and quarterly quota.
- Share what you learn about the market (competitors, objections, pricing) so we can adapt our product and messaging.





How we'll know you're crushing it

- By day 15 you know the product, Portuguese regulations and the pitch inside out, and you're running your first demos.
- By day 25 you have a healthy pipeline in both markets and have closed your first deals.
- By day 50 you're hitting your monthly quota , with your sales cycle and demo-to-close rate on target.

What we're looking for (must-haves)

- Native or bilingual Portuguese (C2).
- Professional Italian (B2+). If you don't speak Italian, we'll also consider another fluent European language.
- Professional English. Spanish is a plus.
- 2+ years as an Account Executive, a closing SDR or in B2B sales, ideally SaaS.
- Experience running a full sales cycle against a quota.
- Comfortable with outbound prospecting and video-call demos.

Bonus points if…

- You know the hospitality, hotel or vacation rental industry in Portugal or Italy.
- You've worked with a CRM such as HubSpot or Salesforce and with prospecting tools.
- You've opened or grown a new market.
- You speak Spanish.

Hiring process

1. Intro call with Talent (30 min), partly in Portuguese and Italian.
2. Interview with our Head of Sales (45 min).
3. Role-play: demo Chekin to a Portuguese or Italian property manager (45 min).
4. Final interview with leadership (30 min).

The whole process takes about 2–3 weeks, and we'll give you feedback at every stage.

? Sound like you? Apply even if you don't tick every box.

Chekin is an equal opportunity employer. We welcome applications from everyone, regardless of gender, age, ethnicity, sexual orientation, disability or any other characteristic.

📌 Account Executive – Portugal + Italy (España)
🏢 Chekin
📍 España