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. As we continue to grow, we are building a world-class sales organization to support our next phase of expansion.

REMOTE (Work may be performed anywhere)

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:

You'll own the segment: the number, the team, the process, and the go-to-market strategy for teams and agents.

• The team. Building, hiring, coaching and leading the sales team as the segment scales.
• Sales enablement. A structured, repeatable sales system: how we qualify, how we run discovery, how we position Rechat, competitive positioning, demo standards, objection handling and deal strategy. Plus the ongoing rhythm of call reviews and coaching that keeps a team improving. The way Rechat sells should belong to Rechat and be consistent across every rep we hire.
• The funnel. Stage definitions, conversion at every step, forecasting, and a scorecard the company can rely on.
• Demand conversion. You won't own marketing spend. You'll own converting what it produces, and telling marketing which channels return revenue rather than volume.
• The customer journey. You'll partner closely with our account management and customer success teams on onboarding, activation, adoption and retention for this segment. You won't manage them, but you'll set the standard for what a successfully onboarded and retained SMB customer looks like, and you'll carry a retention number alongside your growth number.
• Expansion. Growing agent and team adoption inside the brokerages we already serve.
  

What You Bring:

• 7+ years in SaaS or technology sales, including leadership of a high-volume, short-cycle SMB sales motion.
• You've built a system-driven sales motion from scratch. Short cycles, smaller deal sizes, real volume. You designed the process rather than inheriting one.
• You've built the enablement behind it yourself. Playbook, discovery framework, demo standard, competitive positioning, coaching cadence. Written it, taught it, and improved it based on what actually closed.
• You've made a motion less dependent on people over time. You've worked with product and marketing to move work out of humans and into the system, and you can speak specifically to what you automated and what you deliberately kept human.
• You've carried a retention or net revenue number, not just new business. You have a real point of view on why customers leave and what changes it.
• You've hired, ramped and coached reps for this motion, and you know how that profile differs from an enterprise seller.
• You've operated across teams that don't report to you. Marketing, product, account management and customer success all sit outside this role. You've done it without needing the org chart to change.
• You've been hands-on recently. Early on the team is small, and you'll be in the calls and the pipeline yourself. That's the job in year one, not a phase.
• Strong command of funnel economics — conversion, velocity, sales efficiency, forecast discipline, retention and expansion.
• PropTech or real estate technology experience preferred but not required, particularly selling to agents, teams or brokerages. Understanding how this kind of motion is built matters more

Probably Not the Right Fit If:

• Your experience is primarily enterprise, long-cycle, or field sales
• You've led teams inside a machine someone else built, with enablement and operations provided to you
• You want to hand off everything that happens after the signature
• 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.