Senior Account Executive

Extenteam | Full-Time | Remote – United States | Sales

Reporting to: Head of Revenue
Location: Remote-Flexible (U.S.-based) | In-Person Training in Miami + Regular Travel Required
Compensation: $90,000 base + $55,000 on-target variable | $145,000 OTE | Uncapped

 

About Us

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.

We're not looking for someone to manage a territory from a spreadsheet. We're looking for someone to hustle alongside us — someone who takes it personally when a deal slips, who obsesses over their pipeline the way operators obsess over their properties, and who wants to be part of building something real.

 

The Opportunity

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.

The STR industry is fragmented, relationship-driven, and largely underserved by great SaaS. You'll be speaking to operators and property managers who genuinely need what we've built — your job is to find them, earn their trust, and close.

This is not a role for someone who wants to coast on inbound leads or needs a lot of hand-holding. It's for someone who wakes up thinking about their pipeline.

A note on remote: This role has flexibility, but it is not a hide-behind-your-laptop job. You'll start with in-person onboarding and training at our Miami office, travel regularly for industry events and prospect meetings, and show up in person whenever showing up in person is what closes the deal. If your ideal job is 100% on a computer from your couch, this isn't it.

 

What You'll Own

• 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.

 

Quota & Commission Structure

Your quota is weighted toward software, because that's where we're going as a business.

Deal Type	ACV	Commission Rate
Tailwind (SaaS + Shared Services)	~$18,000 ARR	Higher rate
DTM (Dedicated Team Members)	~$30,000 ARR	Standard rate
Enterprise Tailwind / Custom	$500K–$700K+ ARR	Accelerated

• Annual quota target: ~$650,000 ARR (60% weighted toward Tailwind/software)
• Accelerator at 100% quota: 1.5x commission rate
• Accelerator at 125% quota: 2x commission rate
• Upside is uncapped. If you close $1.5M, your W2 reflects it.

 

Who You Are

Required

• 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

Preferred

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

What We Don't Want

• Someone who needs to be managed
• Someone who treats prospecting as someone else's job
• Someone who confuses being busy with being productive
• Someone who applied because "remote" was in the title and has no intention of getting on a plane
• Someone for whom sales is one of several priorities

 

What Success Looks Like

30 days — You know our product cold. You understand the STR competitive landscape. Your first outbound sequences are live and your pipeline is being built.

60 days — Pipeline is qualifying. First Tailwind demos are done. CRM is tight and deal velocity is real.

90 days — First deals closed or at the finish line. You've established a presence in your region. Your quota trajectory is clear.

 

Key Attributes We're Hiring For

Relentless. You don't take silence as a no. You find a way in because that's just how you're wired.

Ownership mindset. Your region is your business. You treat it that way.

Voice at the table. You're not a cog. You're a contributor. We want your market intelligence, your pattern recognition, and your ideas — not just your closed/won column.

Execution over excuses. We're a small team. Everyone ships. Everyone closes. Everyone takes pride in doing great work.

 

Why Extenteam

• 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

 

Our Interview Process

We move fast. Expect to complete the process within 2 weeks.

1. Intro call with Founder (30 min)
2. Head of Revenue interview (60 min)
3. Case study or take-home assignment
4. Reference checks and offer

To apply: Record a short one-minute video explaining why you want to be part of Extenteam and what makes you the right person for this role. We'll know in the first 30 seconds if you've got it.