Commission Microsoft Help Desk Jobs in Springfield, MA

This is a performance-driven, in-home sales role built for professionals who want uncapped earning potential within a structured, supported system. Unlike roles where you build everything from scratch, you step into an established platform designed to help you win.

What You Can Expect

• W-2 employee status (not 1099)
• Uncapped commission structure 
• Estimated first-year earnings: $150,000 - $250,000
• Pre-set, pre-qualified appointments provided
• Additional incentives for self-generated leads
• Company vehicle
• Benefits + 401(k) match
• Paid onboarding and training

What Sets This Apart

• Brand credibility and company-backed marketing
• A proven, structured sales process
• Financing options already in place
• Operational and production support teams
• CRM system (ServiceTitan)

Your focus is selling and serving homeowners - you are not chasing cold leads or building infrastructure. Success here is consultative, not pressure based. Top performers clearly explain value, confidently lead pricing conversations, and execute the sales process with discipline.

Key Responsibilities:

• Conduct multiple in-home inspections and consultations daily
• Diagnose homeowner needs and recommend appropriate roofing or exterior solutions
• Present scope, pricing, and financing options with clarity and confidence
• Guide homeowners through a structured consultation process from inspection to agreement
• Complete contracts and documentation accurately in ServiceTitan
• Maintain professional presentation, organized vehicle, and sales materials
• Generate additional opportunities through referrals and self-sourced leads
• Travel locally to customer homes (field-based role)

What Success Looks Like:

Top performers in this role:

• Execute the full sales process consistently and without shortcuts
• Maintain strong activity levels and pipeline discipline over time
• Use coaching and feedback to continuously sharpen their craft
• Hold value - they don't rely on discounting to win

Who This Role Is a Great Fit For:

• Professionals who have succeeded in commission-based, performance-driven environments
• Clear communicators who can simplify complex information for homeowners
• Individuals comfortable discussing pricing and financing decisions directly
• Self-motivated sellers who take ownership of results and accountability

This Role May NOT Be a Fit If You:

• Rely on pressure tactics or discounting to close
• Resist structured sales processes or coaching
• Avoid direct conversations about money or pricing
• Prefer low-accountability or desk-based environments

Qualifications:

Required:

• Valid driver's license with a clean driving record & background check.
• Comfortable working on roofs, climbing ladders, and accessing attics.
• Strong interpersonal and communication skills to establish rapport and build trust.
• Self-motivated, goal-oriented, and able to work independently or as part of a team.
• Ability to present complex information in an easy-to-understand manner.
• Ability to use CRM software, Microsoft Office, and iOS tools.
• Must be comfortable working in various weather conditions.
• Ability to lift up to 75 lbs

Preferred, not required:

• In-home sales or home improvement sales experience (roofing experience not required).

Training & Support:

• Comprehensive paid training program; 2-week classroom training with additional field training
• Paid training class session (expenses covered)

*Must be comfortable with 2 weeks paid training in another city*

• Ongoing coaching and skill development

Schedule & Work Environment:

• Flexible weekly schedule with evening and weekend appointments as needed.
• Regularly engaged in outside sales, requiring travel to customer locations.

Compensation:

• W-2 employee status (not 1099) with benefits and 401k match
• Paid onboarding and training
• Estimate of First-year earnings: $150,000 - $250,000
• Pre-set and pre-qualified leads provided, with additional incentives for self-generated leads
• Performance-based bonus opportunities

Location: Bloomfield, CT - home office - expected 1-2 days per week for training/meetings (company provided vehicle) 

Job Type: Full-time

FLSA: Exempt