Head of Revenue (Founding Role) - Miami

Head of Revenue (Founding Role) Extenteam | Full-Time | Hybrid | Executive Leadership

Location: Hybrid - Regular in-person time at our Miami office expected.
Base Salary: $160,000 – $180,000 OTE: $224,000 – $252,000 (base 40% variable) Equity: 0.25% – 0.75%

About Extenteam

Extenteam started as a staffing service for short-term rental operators. What we built instead was something bigger.

Today, we are the orchestration layer for the best property management companies in North America,  powering their operations through AI-driven software, shared services, and dedicated team members. We serve 50,000 properties, count some of the largest PE-backed operators and publicly traded REITs among our clients, and have been profitable since inception.

2026 is not business as usual. It is a rebirth.

We are fundamentally reshaping how Extenteam goes to market - new platform, new positioning, new commercial infrastructure. Unit count is growing exponentially, our SaaS platform is scaling fast, and we are building the revenue function to match. We're targeting growth from $1MM MRR to $2M MRR by December 2026. We're hiring the person who will own that number, build the team that hits it, and grow into the revenue leader this company deserves.

The Opportunity

This is a founding revenue role, and a genuinely rare one.

We're not hiring a manager to inherit a machine. We're hiring a builder who will own the entire revenue motion from first touch to closed deal, from first BDR hire to a scaled AE team. You will define how Extenteam wins in the market, personally carry and close enterprise accounts, and build the commercial infrastructure around you as you go.

You report directly to the founder. You own revenue end-to-end. And you are joining at exactly the right moment, when the foundation is proven, the momentum is real, and the ceiling is wide open.

Our Three Revenue Streams

SaaS / AI-Powered Orchestration Layer Our core platform: AI-assisted guest communications, workflow automation, and operational intelligence built specifically for STR operators. The primary GTM focus for this role.

Shared Services Human-in-the-loop operational support - guest communications, reservations, and daily workflow management delivered by our specialist teams.

Dedicated Team Members Trained, embedded overseas talent on a recurring model,  giving operators the people they need to scale without the overhead.

What You'll Build & Own

The Revenue Function - End to End

• Own the entire revenue motion from demand generation through close, this is not a partial ownership role or a “consultant” or strategist role. This is a HANDS ON - IN THE WEEDS role.
• Design and build the AE and BDR team structure, hiring plan, and onboarding playbook
• Create the sales motion, ICP definition, sequencing, and objection frameworks the team executes
• Establish the revenue operating model: pipeline metrics, forecasting, dashboards, and CRM discipline

Your Own Book of Business

• Personally prospect, qualify, and close mid-market and enterprise PMCs (50 units)
• Own high-value accounts from first conversation through negotiation and close - you are not delegating this
• Lead commercial conversations with senior operators, PE-backed platforms, and institutional real estate companies

GTM Strategy

• Define go-to-market motion across all three revenue streams, with SaaS as the primary growth lever
• Partner with Product on messaging, positioning, and roadmap alignment
• Collaborate with or oversee demand generation - content, events, digital - to build inbound pipeline

Team Leadership

• Recruit, coach, and develop AEs and BDRs as headcount scales
• Run weekly pipeline reviews, 1:1s, and performance cadences
• Build a culture of accountability, ambition, and collaboration

Who You Are

Required

• Deep knowledge of the short-term rental or property management industry,  you know the players, the pain, and how they buy
• 7 years in B2B sales with at least 3 years carrying your own quota in a senior role
• Experience building or significantly scaling a revenue function, playbooks, hiring, process, from scratch
• Proven track record closing mid-market or enterprise deals through complex, multi-stakeholder cycles

Hands-on and hungry - you close deals yourself while building the team around you

• Ambitious team player - you want to grow with the company, not just in it
• Ideally Based in Florida or committed to regular Miami office presence
• Ambitious on automation, next gen tech stack. We are not looking for someone to simply implement a playbook from five years ago. 

Preferred

• Background in proptech, hospitality tech, or vertical SaaS for property managers or STR operators
• Experience at a company going through a transformation or services-to-SaaS transition
• Familiarity with AI-assisted GTM tools and modern sales stacks
• Comfortable operating in a high-involvement founder-led environment

Key Attributes

• End-to-end owner  you think and operate across the full revenue cycle, not just your slice of it
• Founding energy - you thrive with a blank canvas and move fast without waiting for permission
• Hands-on closer - you are in deals every week, not coaching from the sideline
• STR fluent - you earn credibility with an operator in the first five minutes
• Builder and leader - you can architect process and develop people simultaneously
• 2x mindset - you think in terms of doubling what exists, not maintaining it

What Success Looks Like

• 30 days: Deep context on ICP, competitive landscape, and existing pipeline. Personal pipeline seeded. Revenue function gaps mapped. First AE up and running
• 60 days: First enterprise deals progressing. BDR/AE hiring plan in motion. Sales playbook v1 drafted. Forecasting running. Personal quota on track. First closed wins. 
• 90 days: Team structure taking shape. Clear path to MRR targets defined.

Why Extenteam

• Own it from day one - founding revenue leader at a company mid-transformation, not inheriting someone else's structure
• Sell something that works - 300 PMC clients, 50,000 properties, PE and REIT-level credibility, profitable since inception
• Build the team - rare chance to hire and shape the AE/BDR org yourself from the ground up
• Executive access -  report directly to the founder; your voice shapes company direction
• Real upside - $160K–$180K base, $224K–$252K OTE, 0.25%–0.75% equity at a company mid-inflection

Our Interview Process

We move quickly - expect 2 weeks from first conversation to offer.

1. Intro call with Founder (30 min)
2. Take-home case study
3. Team interviews
4. Reference checks offer

To apply: Record a short one-minute video telling us why you want to join Extenteam and what makes you the right person for this role.