Head of SMB

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 agent revenue, and it is two jobs. 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 run a sales floor, because the deals that justify a human still need one. Hiring, ramping, enablement, coaching, quota and comp. The floor exists to serve the engine, not to replace it. 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 not a traditional sales leadership job, and the difference matters. 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 number. New revenue from agents and teams, revenue per agent, and gross retention in the segment. The go-to-market. Channels, pricing, packaging, positioning and partnerships for agents and teams. 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 built and owned a sales floor. You grew a team from a handful of reps to fifty or more, or something close to it. You hired them, ramped them, coached them, and managed people out when needed. You can tell us what the team looked like when you arrived and when you left. 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.