| Location | Loves Park, IL (Remote) |
Inside Sales Representative / Experienced Sales Closer
SeamlessGutters.com Coaching and Membership Programs
Location: Remote
Position: Full-Time Sales Representative
Compensation uncapped commission
If you are a disciplined closer who wants to sell something that genuinely helps business owners grow, this is your opportunity to make a real impact.
At SeamlessGutters.com, you will do more than sell a program. You will help gutter contractors across the country move from chasing jobs to building scalable, profitable businesses. Every conversation is a chance to help an owner solve deeper problems around sales, hiring, systems, leadership, and growth.
This is not traditional directory sales, and we do not sell shared leads.
We are building a national contractor-growth platform that helps gutter company owners build real businesses through better systems, sales processes, leadership, and operating procedures.
Our programs combine decades of gutter-industry experience with a disciplined, high-accountability sales and business-development approach influenced by the Andy Elliott training style.
Why This Role Matters
You will be the person who helps contractors see what is possible for their business, understand what is holding them back, and take action.
You will guide business owners through meaningful sales conversations that uncover real operational and revenue challenges. When you close the right contractor into the right program, you are not just generating revenue, you are helping create stronger companies, better teams, and more predictable growth for owners who are ready to level up.
This is an ideal role for a high-accountability sales professional who wants to sharpen their craft, be coached, and grow with an expanding national platform.
What You Will Sell
SeamlessGutters.com Membership
Our membership helps gutter contractors improve their businesses through:
Weekly live coaching
Sales-process development
Standard operating procedures
Hiring and employee-development systems
Pricing and estimating guidance
Operational-efficiency training
A verified SeamlessGutters.com Trusted Member profile
National website visibility and local SEO benefits
Exclusive homeowner estimate requests
Access to a network of serious gutter contractors
Charter Membership is currently available to a limited number of qualified contractors at $199 per month, locked in for life, before the public rate increases to $499 per month.
Coaching and Business-Growth Programs
You will also sell higher-level coaching and implementation programs that help contractors:
Build repeatable SOPs
Develop stronger sales teams
Improve closing percentages
Hire, train, and manage employees
Create company-wide accountability
Improve lead handling and follow-up
Build predictable revenue
Move from job-to-job work to a scalable business
What You Will Own
You will own sales conversations with gutter contractors who apply, inquire, or enter our pipeline and turn interest into action through a professional, structured process.
Your day-to-day opportunities will include:
Connecting with gutter contractors who apply, inquire, or enter our sales pipeline
Running discovery calls with business owners to uncover real growth barriers
Identifying operational, sales, hiring, and revenue problems that need to be solved
Matching each qualified contractor with the right membership or coaching program
Following a structured sales process that creates consistency and trust
Handling objections professionally and directly while protecting value
Driving thoughtful, persistent follow-up until a clear decision is reached
Closing qualified contractors into the right program
Owning CRM accuracy through clear notes, follow-up dates, and pipeline stages
Participating in sales training, call reviews, role-playing, and accountability meetings to continuously improve your performance
Hitting activity, appointment, closing, and revenue goals
What Success Looks Like
Success in this role is not about hard selling for the sake of it. It is about earning trust, diagnosing business needs, communicating value clearly, and helping the right contractors commit to change.
The right person will know how to ask tough questions, uncover the cost of inaction, and confidently ask for the sale.
Who We Are Looking For
We want an experienced closer who understands that professional sales requires preparation, discipline, follow-up, and accountability.
You should be comfortable selling directly to business owners and discussing real business problems, including:
Inconsistent revenue
Poor lead follow-up
Low closing percentages
Lack of documented processes
Difficulty hiring and managing employees
Weak pricing or estimating systems
Owners trapped in daily operations
Companies generating work without building a real business
You are likely a strong fit if you are energized by direct conversations, measurable outcomes, and the opportunity to improve through coaching and call review.
Required Qualifications
Proven experience closing coaching, consulting, memberships, SaaS, marketing services, or other B2B offers
Strong phone and video-call closing ability
Experience selling to entrepreneurs or small-business owners
Ability to follow a defined sales process
Strong objection-handling and follow-up skills
Comfort discussing monthly recurring memberships and higher-ticket coaching programs
Self-motivated and able to work remotely
Coachable, competitive, organized, and accountable
Comfortable having sales calls reviewed for training and improvement
Able to communicate professionally without sounding scripted or overly polished
This Position Is Not for You If
You wait for easy leads to close themselves
You avoid direct financial or business questions
You give up after one or two follow-up attempts
You blame the lead, price, market, or company when you miss goals
You are uncomfortable being coached or having your calls reviewed
You want a low-pressure customer-service position
You need constant supervision to complete daily responsibilities
Why SeamlessGutters.com
SeamlessGutters.com has served the gutter industry online since 1998 and is backed by 37 years of direct industry experience.
We understand gutter contractors because we have worked in the industry, trained contractors, developed sales systems, and built operating processes that work in the field.
We do not teach generic business theory.
We help contractors implement practical systems for sales, estimating, hiring, leadership, operations, and profitable growth.
This is an opportunity to join the company during the early expansion of a national coaching and contractor-membership platform.
For the right sales professional, this means the chance to join at a meaningful stage, sharpen your skills, contribute directly to growth, and build momentum with a company creating something valuable in a specialized industry.
Performance Expectations
Your performance will be measured by:
Qualified conversations
Appointments conducted
Follow-up activity
Memberships sold
Coaching programs sold
Closing percentage
Monthly recurring revenue
Total collected revenue
CRM accuracy and pipeline management
How to Apply
Submit your resume and a short video or written introduction explaining:
What you have sold
The average price of the offers you have closed
Your previous closing percentage
Your experience selling to business owners
Why you believe you can sell coaching and membership programs to gutter contractors
An example of how you handle the objection, "I need to think about it."
Applicants who cannot provide measurable sales results will not be considered.