Inside Sales Specialist

Inside Sales Specialist

Greater Chicago Area

About Win: Win ( is the #1 ranked home services franchise in its category and a proud member of the Entrepreneur 500. Backed by three decades of excellence, we're on a mission to build a global brand by transforming the $250+ billion U.S. residential services market through AI-driven innovation, exceptional customer experience, and operational excellence. Combining the stability of an established leader with the energy of a fast-growing organization, Win offers driven, like-minded professionals a unique opportunity for meaningful personal and professional growth.

About The Inside Sales Specialist Job: We're looking for a dynamic, personable Inside Sales Specialist to help aspiring business owners explore the opportunity to start their own Win franchise. This isn't your typical sales role. You won't be cold-calling or pitching. Instead, you'll serve as the first point of contact for qualified candidates who have expressed interest in Win. Your job is to guide these individuals through a structured discovery conversation, help them understand the Win opportunity, and build meaningful, trust-based relationships. This is a hands on role.

Qualities That'll Set You Up For Success In This Role:

• A people person with exceptional interpersonal and communication skills
• Naturally curious and a great listener
• Empathetic, thoughtful, and energized by helping others succeed
• Organized, proactive, and motivated by goals and results
• Comfortable managing multiple conversations and follow-ups using a CRM system
• Able to work independently with discipline while enjoying team collaboration

Who Is This Role Perfect For? We're not looking for traditional sales experience. If you're someone with 5+ years of full-time professional experience, who connects easily with people and enjoys high-touch communication, this role could be a great fit. You might currently be in a role such as:

• Marketing coordinator or client-facing account manager
• Operations or administrative specialist with frequent stakeholder interaction
• Recruiter, admissions advisor, or small business consultant

These are just examples. If you thrive on conversations and relationships, and have a strong desire to grow in an environment of continual learning and hands-on training, we want to hear from you, regardless of your background.

What You'll Do:

• Conduct scheduled intro calls with inbound leads from Win's marketing funnel
• Guide candidates through an introductory discovery process using Win's presentation
• Use our CRM system to manage contacts, schedule touchpoints, and track progress
• Collaborate with the team to continuously improve the candidate experience and journey

What We Offer:

• Comprehensive onboarding and training to set you up for success
• A mission-driven, inclusive culture built on respect and collaboration
• Paid medical, dental, and vision coverage
• 401(k) matching
• Remote work flexibility and technology stipend
• Opportunities to grow in a highly innovative environment with a nationally recognized brand

Our Culture: We're builders, listeners, and optimists. At Win, we value initiative, integrity, and a genuine spirit of collaboration. Our team celebrates wins big and small, supports each other's growth, and leads with empathy. Meet our team and culture ?

Win is proud to be an Equal Opportunity Employer. All applicants will receive consideration without regard to race, gender, disability, religion, sexual orientation, or any other protected characteristic.