[Hiring] Senior Account Executive @Extenteam Careers

Role Description

This is a full-cycle, quota-carrying AE role with a clear focus on Tailwind software sales. You'll own new business development across your assigned region, with a compensation structure that rewards software and platform deals above all else.

• Pipeline from zero. You build it. You own it. No one is handing you leads on a silver platter.
• Run discovery, demos, proposals, and close — full-cycle, top to bottom.
• Prioritize Tailwind platform deals and enterprise partnerships; support DTM deals as part of a complete solution.
• Work the phones, LinkedIn, email, text, and in-person events — whatever it takes to get in the room.
• Travel to STR industry conferences, trade shows, and key prospect meetings throughout the year — this is a core part of how you build pipeline, not an optional add-on.
• Complete onboarding and initial training in person at our Miami office — we invest in getting you ramped right from day one.
• Use AI tools to work smarter — automate the admin, spend time on conversations that close.
• Keep CRM tight. If it's not in HubSpot, it didn't happen.
• Feed insights back to the product and leadership team — your voice shapes the roadmap.

Qualifications

• 3+ years of full-cycle B2B sales experience with a provable track record of hitting or exceeding quota.
• You're a hunter — you've built pipeline from scratch before, and you know what that takes.
• CRM discipline (HubSpot preferred) — you manage your pipeline like a professional.
• Exceptional written and async communication — you move deals forward between calls, not just on them.
• Ability and willingness to travel 25–30% — conferences, trade shows, prospect visits, and team meetups; no travel restrictions.
• Willing and able to travel to Miami for initial onboarding, training, and periodic team offsites.
• Sales is your priority — not a side hustle, not a stepping stone; you are all in.
• U.S.-based.

Requirements

• SaaS or subscription sales experience (preferred).
• Short-term rental, hospitality, or property management industry background (preferred).
• SMB and mid-market selling experience — you know how to run fast cycles and still close enterprise when it counts (preferred).
• Experience in a fully remote role — you don't need an office to stay sharp (preferred).

Benefits

• Uncapped upside — a strong closer here can earn $200K+.
• Direct access to leadership — you'll work side-by-side with the Head of Revenue and have direct visibility to the Founder.
• Voice at the table — your feedback shapes product, go-to-market, and how we win.
• Real market whitespace — the STR industry is fragmented and largely underserved; you're not walking into a saturated market.
• Flexibility with accountability — you manage your own schedule, but results are what matter.

Company Description

We're Extenteam — a lean, high-output team that's built a $10M ARR business in the short-term rental industry and is now scaling fast. We're transitioning from a professional services model to a software-first, subscription-led business, and we need the right people to help us get there.

• Our flagship product, Tailwind, is a guest communication platform that blends SaaS automation with a shared services layer — built specifically for short-term rental and property management operators.
• We also place Dedicated Team Members (DTMs) with operators who need trained, reliable overseas talent on a recurring premium model.
• We are 50 people at the core with 350+ DTMs supporting our customers.
• No bureaucracy. No endless approval chains. If you have a good idea, you say it, and it gets heard.
• We move, we build, and we win together.