Head of Agent and Team Revenue

Rechat is the operating system for real estate. Marketing, CRM, transactions, listings and AI in a single product, replacing the disconnected stack of tools most agents are forced to stitch together. 

We partner with brokerages, teams and agents across North America to modernize how real estate is marketed, managed and transacted. Some of the largest brokerages and networks on the continent run their business on us, and tens of thousands of agents use Rechat every week.

We have spent the last two years rebuilding the product to be AI-native, and we are growing quickly.

REMOTE (Work may be performed anywhere)

The Role

Rechat is well established at the top of the market. Underneath those enterprise relationships sit tens of thousands of agents, and over the last two years individual agents and small teams have started buying from us directly, largely on their own. We have never pursued that market deliberately. There is no system behind it. You are here to build one.  This role owns revenue from agents and teams — from acquisition and activation through monetization, expansion and retention. There are two major parts to the job.

1. Build a touchless engine that opens up selling to agents and teams at scale.  The product has to do most of the selling. An agent should be able to find us, sign up, get value and start paying without ever speaking to a person. This is a high-volume, short-cycle motion at a price point that cannot support many human hours per customer. The answer is not more salespeople working harder. It is a system: demand from channels rather than headcount, a repeatable process every rep works from,and onboarding and adoption carried largely by the product. Around that engine, you will build and lead the sales motion for the opportunities that justify human involvement — hiring, ramping, enablement, coaching, quota and compensation. Sales is one part of the revenue engine, not the engine itself.

2. Raise what every agent pays us.  Tens of thousands of agents already use Rechat through their brokerage's contract and pay us very little directly. Selling them premium products, our websites, AI marketing, advertising and social, is the fastest revenue available to us and it has never had an owner. We are looking for someone who has built this before. Not someone smart who could figure it out with us. Someone who has personally designed and run a mostly touchless, system-driven SMB motion, has made the mistakes, and knows what works.

This is a revenue leadership role, not a traditional sales leadership role, and the distinction matters. You will own how agents and teams discover Rechat, activate, buy, expand and stay — with product, marketing, sales and customer success each serving as levers of the same revenue engine.

Selling to teams and agents is a high-volume, short-cycle motion at a price point that cannot support a lot of human hours per customer. The answer is not more salespeople working harder. It's a system: demand that comes from channels rather than headcount, a repeatable process every rep works from, and onboarding and adoption carried largely by the product.

We're looking for someone who has built that system before. Not someone smart who could figure it out with us. Someone who has personally designed and run a mostly touchless, system-driven SMB motion, has made the mistakes, and knows what works.

What You'll Own:

• The revenue number. New revenue from agents and teams, revenue per customer, expansion revenue, attach rate, and gross retention across the segment.
• The revenue strategy. How we acquire, convert, monetize and expand agents and teams — including channels, pricing, packaging, positioning and partnerships.
• The self-serve path. Signup, activation, checkout and upgrade, defined with our product team.
• The team. Hiring, ramping, coaching and leading the sales floor as it scales.
• Sales enablement. Playbooks, training, certification, call libraries, objection handling, and the onboarding that makes a new rep productive in weeks rather than quarters.
• Websites and AI marketing products. The highest-value thing we sell an agent. Pricing, packaging, launch and attach rate.
• Expansion into our existing agent base. Upsell and cross-sell to agents who came to us through a brokerage.
• Forecasting and pipeline discipline. Capacity planning, conversion, velocity, sales efficiency.
• The customer journey after the signature. You will partner closely with our account management and customer success teams. You will not manage them, but you will set the standard for what a successfully onboarded and retained customer looks like, andyou carry a retention number alongside your growth number.
• The relationship with demand generation. You define the pipeline you need, agree the definitions, and hold both sides to the numbers.

What You Bring:

Be prepared to walk us through each of these in detail.

• You have owned a meaningful revenue business. You have carried a revenue number for a high-volume SMB, prosumer or consumer-like segment and owned the levers behind it - acquisition, conversion, sales, monetization, expansion and retention. You can tell us what the business looked like when you arrived, what you changed and what happened to the numbers.
• You have built and led a high-velocity sales organization. You have hired, ramped, coached and managed salespeople at scale, and you know when a customer should be served by a rep versus by the product.
• You built the system, not just the team. Onboarding programs, certification, playbooks, scorecards. You can tell us what your ramp time was and how you shortened it. 
• You have run a real coaching cadence. Weekly one to ones, recorded call reviews, live coaching, performance plans. Tell us your quota attainment rate, because the industry average is under half and we want someone who has beaten it.
• You have designed comp plans and quota structures yourself, along with territory or lead routing, and lived with the consequences.
• You have built a touchless or self-serve motion. A path where the product does the selling: signup, trial, activation, checkout, upgrade. If you have taken a business from fully rep-led to substantially self-serve, that is the most relevant thing on your resume.
• You have owned the full journey, not just the close. Acquisition through activation, monetization and retention. You have a real point of view on why customers leave and what changes it, and you understand that in a high-volume business most churn is
  decided at the point of sale.
• You have grown revenue inside an existing customer base, not only through new logos. Upsell, cross-sell, expansion.
• You have sold a subscription in the low thousands of dollars a year, on a two to four week cycle, to individuals or small businesses.
• You have used AI seriously inside a sales organisation. Not as a talking point. What you automated, what it replaced, and what it did to your cost per meeting.
• You have operated across teams that do not report to you. Marketing, product,account management and customer success all sit outside this role. You have done it without needing the org chart to change. 
• You have been hands-on recently. Early on the team is small and you will be in the calls and the pipeline yourself. That is the job in year one, not a phase.
• Strong command of funnel economics: conversion, velocity, sales efficiency, forecast discipline, retention and expansion.
• 7+ years in sales leadership, with meaningful time in a high-velocity SMB or prosumer
  motion. 
• PropTech or real estate experience preferred but not required. Understanding how this kind of motion is built matters more. Our strongest analogues sit in website and hosting platforms, SMB vertical software, insurtech and marketplaces, and SMB payments and payroll.

Probably Not the Right Fit If:

• Your experience is primarily enterprise, long-cycle or field sales
• You have led teams inside a machine someone else built, with enablement and operations provided to you
• You want to inherit a functioning sales organisation rather than create one
• You want to hand off everything that happens after the signature
• Your answer to a missed number is more headcount
• You need a large team and a full support function around you to be effective

How You Work:

• Clear, direct written communication. Most coordination happens in Slack and project tools, not meetings.
• Fluent with modern AI tools and using them daily to move faster.
• Comfortable in a CRM as an operator, not just a reviewer. HubSpot experience preferred.
  

Why You'll Love Working Here:

• Competitive compensation
• Fully remote with flexible work/life balance
• A diverse, inclusive, and highly collaborative culture
• Meaningful work with a product used by real professionals every day
• Flexible Paid Time Off

We are an equal opportunity employer committed to building a diverse and inclusive team. All employment decisions are made without regard to legally protected characteristics. Background and reference checks required.