Head of Sales, Roofing Partnerships

About RAKE ML

RAKE ML is building AI driven software for one of the largest and most underserved contractor markets in the country: residential roofing.

Our platform uses aerial imagery, property data, storm history, roof age, CRM data, and machine learning models to help residential roofing companies predict which homes are most likely to need work and turn those predictions into outbound sales.

We are early, moving fast, and building a new way for roofing companies to find demand, prioritize opportunities, and grow revenue.

About the Role

We are hiring a Head of Sales, Roofing Partnerships to help bring RAKE ML into the residential roofing market.

This is a sell first leadership role. The first job is to win customers directly. You will own the full sales cycle from outbound prospecting through discovery, follow up, and close. Over time, you will help turn early sales activity into a repeatable sales motion.

This role requires consistent outbound activity, strong follow up, and a high level of ownership. The person who succeeds here will be comfortable working hard, moving quickly, and staying close to customers as we build the sales motion.

In return, you will receive meaningful early employee equity, direct access to the founders, and the opportunity to help build RAKE ML’s roofing sales engine from the ground up.

What You’ll Do

● Cold call, prospect, and close residential roofing companies

● Own the full sales cycle from first touch through close

● Test sales angles around AI roof targeting, storm exposure, CRM analysis, and outbound homeowner campaigns

● Help identify the strongest roofing segments, markets, and offers

● Bring customer feedback back into product, pricing, and positioning

Who We’re Looking For

We are looking for a high ownership sales leader who understands contractors, can speak naturally with roofing owners, and is excited to help build the sales motion from the ground up.

You should have

● 5+ years of sales experience

● Experience selling to roofers, contractors, home services companies, restoration companies, solar companies, exterior remodelers, or similar customers

● Comfort with outbound prospecting and direct owner conversations

● Ability to run discovery, manage follow up, and close customers

● Strong judgment, clear communication, and high ownership

● Comfort working in an early stage startup where the playbook is still being built

Bonus experience includes residential roofing, storm restoration, roofing software, insurance restoration workflows, direct mail, canvassing, appointment setting, or tools like AccuLynx, JobNimbus, CompanyCam, Xactimate, Roofr, or EagleView.

Compensation

The full time compensation package includes

● Base salary: $100,000 to $110,000, based on experience

● Equity: meaningful early employee equity

● Benefits: included as part of the full time package

● Performance based upside: potential for additional upside as sales targets, pricing, and the repeatable sales motion are established

We expect this role to begin with a 60 day paid trial to confirm fit, pace, sales ability, market understanding, and ability to work closely with the founders. Trial compensation will be paid monthly and agreed before the start of the trial.

Why Join RAKE ML

This is a chance to join an early AI company before the sales engine is built.

You will be close to the founders, close to customers, and close to the decisions that matter. Your work will directly shape how RAKE ML sells, grows, and defines a new category of roofing software.

If you want to sell, build, learn fast, and earn real ownership in an early stage company, we would love to meet you.

Location and Work Authorization

This is a remote role based in the United States.

Candidates must be legally authorized to work in the United States.

Company DescriptionRAKE ML is building AI driven software for one of the largest and most underserved contractor markets in the country: residential roofing.

Our platform uses aerial imagery, property data, storm history, roof age, CRM data, and machine learning models to help residential roofing companies predict which homes are most likely to need work and turn those predictions into outbound sales.

We are early, moving fast, and building a new way for roofing companies to find demand, prioritize opportunities, and grow revenue.