[Hiring] Head of SMB @Rechat Inc

Role Description

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.

What 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 including how we qualify, run discovery, position Rechat, competitive positioning, demo standards, objection handling, and deal strategy.
• The funnel: Stage definitions, conversion at every step, forecasting, and a scorecard the company can rely on.
• Demand conversion: Converting what marketing produces and telling marketing which channels return revenue rather than volume.
• The customer journey: Partnering closely with account management and customer success teams on onboarding, activation, adoption, and retention for this segment.
• Expansion: Growing agent and team adoption inside the brokerages we already serve.

Qualifications

• 7+ years in SaaS or technology sales, including leadership of a high-volume, short-cycle SMB sales motion.
• Experience building a system-driven sales motion from scratch.
• Designed the process rather than inheriting one.
• Built the enablement behind it yourself, including playbook, discovery framework, demo standard, competitive positioning, and coaching cadence.
• Experience in making a motion less dependent on people over time.
• Worked with product and marketing to automate processes.
• Carried a retention or net revenue number, not just new business.
• Real point of view on why customers leave and what changes it.
• Hired, ramped, and coached reps for this motion.
• Operated across teams that don't report to you.
• Hands-on experience, especially in the early stages of team development.
• Strong command of funnel economics—conversion, velocity, sales efficiency, forecast discipline, retention, and expansion.
• PropTech or real estate technology experience preferred but not required.

Requirements

• Experience primarily in enterprise, long-cycle, or field sales is probably not the right fit.
• Leading teams inside a machine built by someone else, with enablement and operations provided to you, is not suitable.
• Desire to hand off everything that happens after the signature is not a match.
• Need for a large team and a full support function around you to be effective is not aligned with this role.

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.

Benefits

• 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.