Job Description

Account Executive

Company: Roof AI

Location: Hybrid (Montreal preferred)

Type: Full-time

Start Date: January 2026

About Roof AI

Roof AI is a Montreal-based software company that helps leading real estate brands like RE/MAX, Coldwell Banker, and HomeServices of America turn passive website traffic into real conversations, real leads, and real appointments.

Our AI-powered digital assistant engages every lead in real time, qualifies them based on intent, and instantly routes them the right way. No more missed opportunities, no more slow response times.

We’re a lean, fast-growing team backed by years of product development and strong traction with some of the most recognized brands in real estate.

We sell to brokerages of different sizes. Deal sizes are meaningful. You will sell to operators, marketing leaders, and executives who have been burned by vendors before.

This is not a plug-and-play AE role. You will help define how we sell.

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The Role

We are looking for an Account Executive who can own the full sales cycle and help mature our GTM strategy. You will work closely with the founders, product, growth, and customer success teams. You will talk to prospects early, shape positioning, and close real revenue.

If you like clarity, ownership, and selling something that actually works, keep reading.

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What You’ll Do

Own Revenue

• Run the full sales cycle from first call to contract
• Navigate and lead multi-stakeholder conversations to uncover needs, create urgency and deliver Roof AI’s value proposition
• Maintain accurate forecasting, pipeline management and deal tracking in Salesforce

Shape the Sales Motion

• Give direct feedback on messaging, pricing, and ICP
• Help refine what a “qualified” account actually is
• Build and qualify pipeline, while also running your own targeted outbound prospecting to strategic accounts
• Improve demos, discovery, and deal flow over time

Work Cross-Functionally

• Partner closely with Customer Success to ensure clean handoffs
• Work with Growth team on sales and marketing strategy
• Feed real market insight back to product

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What We’re Looking For

Must-Haves

• 3–6 years of B2B SaaS sales experience
• Experience owning deals end-to-end
• Comfort selling to mid-market and enterprise buyers
• Strong discovery skills — you ask good questions and listen
• Clear communicator — you can explain complex things simply
• High level of accountability with consistent follow-through

Strong Pluses

• Experience selling to real estate, proptech, or local businesses
• Experience selling marketing, data, or workflow tools
• Early-stage startup experience
• Comfort with ambiguity and evolving processes
• Familiarity with AI tools

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What Success Looks Like

• You are consistently closing deals
• You understand our best buyers better than we do
• You help sharpen our ICP and disqualify faster
• You contribute to a repeatable sales motion
• Founders trust you with deals without micromanagement

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Why Join Roof AI

• Product works. Customers see real impact
• Small team. High trust. Low politics
• You will influence how this company sells, not just hit a number
• Direct access to leadership and product
• A technical product in a niche vertical with real pain and buying intent
• Clear path to senior AE or sales leadership as we scale

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Compensation

• Competitive base + commission + benefits
• Meaningful upside for strong performers
• Details discussed with qualified candidates

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