Account Executive
1 week ago
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.
⸻
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.
⸻
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
⸻
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
⸻
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
⸻
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
⸻
Compensation
Competitive base + commission + benefits
Meaningful upside for strong performers
Details discussed with qualified candidates
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