Location: Miami, FL - in-office 4 days per week

Compensation: $80,000 base + $40,000 commission ($120,000 OTE)

About Us

We are Extenteam, a company revolutionizing the short-term vacation rental industry. We are transitioning from a professional services model to a software-first subscription model. Our primary focus is Tailwind, our AI-powered guest communication and operations platform built specifically for short-term rental property managers.

We generate revenue through four primary streams:

Dedicated Team Members: Providing trained overseas talent with a recurring premium model, replacing one-time recruitment fees and giving operators a reliable, scalable workforce.

Managed Services - Shared Services: A fully managed operations layer that handles day-to-day guest communication and operational tasks on behalf of property management companies, powered by our agent team and Tailwind platform.

Tailwind - SaaS Platform: A guest communication platform blended with our shared services team, supporting short-term rental operators in streamlining operations, automating repeatable tasks, and improving response times across all communication channels.

x10 Labs: Extenteam's innovation lab that helps vacation rental operators improve efficiency through automation and AI - delivering both custom project-based solutions and recurring automation products built specifically for the short-term rental industry.

Extenteam is a small but mighty core team of 50 across Sales, Partner Success, Marketing, HR, Engineering, Product, and Admin. We have hubs in Miami, LA, and Medellin, with expansion into Europe underway. Our core team is supported by 350+ dedicated team members servicing our customers.

We are building a team with an ownership mindset that values execution and urgency above all else.

The Opportunity

You will be the first SDR, focused on driving new business across all Extenteam products, with a primary emphasis on Tailwind, our Shared Services platform. There are no inbound leads, we are building the process from scratch. Your job is to get Extenteam in front of every property management company in your market through relentless, multi-channel outbound outreach - cold calls, emails, LinkedIn, texts, and showing up in person - whatever it takes.

What You Will Do

• Build your pipeline from zero
• Execute high-volume, multi-channel outbound daily: cold calls, cold emails, LinkedIn, SMS, and in-person outreach
• Become the go-to Extenteam contact for every property manager in your market
• Schedule meetings with prospects & route them to AE
• Run the discovery process (alongside the AE) to understand the prospect’s pain points and position our solution
• Leverage AI as much as possible to make the job more efficient
• Maintain tight CRM hygiene in HubSpot
• Attend industry conferences
• Collaborate with team to refine messaging, ICP, and outbound strategy as we learn what works

Who You Are

Required

• 2-4 years of sales experience with a demonstrated ability to generate your own pipeline through outbound activity
• Cold calling every day (number will be determined once we start)
• Full-cycle B2B sales experience, from prospecting to close
• Urgency is your default setting
• Experience using CRM tools like HubSpot
• Analytical thinking and ability to make decisions based on data
• Strong interpersonal and phone skills
• Strong work ethic
• Ability to travel up to 20% of the time
• Must be within commutable distance to Miami, Florida or willing to relocate

Preferred

• SaaS selling experience
• Short-term rental or property management industry experience
• SMB seller experience
• Experience using AI tools to build outbound sequences or research prospects at scale

Key Attributes

• Thick Skinned: You hear no constantly and it does not slow you down. You treat rejection as data and keep trying
• Market Ownership: You understand your region deeply and build a presence that makes you the go-to person
• Execution Focused: You move quickly, prioritize high-impact activity, and deliver results consistently
• Data Driven: You use data and tools to work smarter, not just harder

What Success Looks Like

• 30 days: Deep understanding of all Extenteam products, ICP, and competitive landscape. Already started cold calling, sequences, LinkedIn, & personalized emails.
• 60 days: Qualified pipeline growing from your own outbound activity. First meetings with target operators complete. CRM hygiene tight and activity metrics on track.
• 90 days: First deals closed or in final stages. Outbound engine running consistently. Market presence established in your region.

Why Join Extenteam

• First mover advantage: You would be the 1st SDR at Extenteam and will shape how we sell.
• Market ownership: Own your region with full autonomy to build your pipeline and presence the way you see fit
• Executive visibility: Report directly to the GTM Lead and collaborate with the leadership team including our CRO & founder
• Ownership and autonomy: We trust you to own your market and make proactive decisions to drive new business
• Growth trajectory: As we scale, you will expand your market, be part of product expansion, and grow your career
• Competitive compensation: $80,000 base + $40,000 performance bonus ($120,000 OTE)
• Miami-based team: Work alongside a talented, in-office team 4 days per week in Downtown Miami

Our Interview Process

We move quickly for the right candidate. You can expect to complete the process within 2-3 weeks.

• GTM Lead & CRO interview (60 min)
• 5-min coldcall roleplay
• Normal interview after
• Founder interview (30 mins)
• 5-min coldcall roleplay
• Normal interview after
• Take home assignment (1 hr)
• Find 10 leads and explain outreach to them (process & message(s))
• Reference checks and offer