Job Description
In-House Sales Strategist
Location: Remote (with limited travel)
Reports to: CEO & Business Development Director
Organization: Wynter Immigration Law Academy (WILA), Home of the Legal Rebels
About Us
Wynter Immigration Law Academy (WILA) is the trailblazer in training non-attorneys to legally and ethically offer immigration services across the U.S. We are where immigration meets innovation — training tomorrow’s Legal Rebels to launch profitable, ethical immigration businesses.
The Role
We are seeking a results-driven, heart-centered In-House Sales Strategist to drive enrollment and expand access to WILA programs for aspiring immigration professionals. You’ll serve as the first point of contact for prospective students — listening closely, identifying needs, and offering aligned program pathways that support both their personal and professional goals.
You’ll build strong relationships, support our application pipeline, and ensure that every conversation reflects the care, integrity, and bold vision WILA is known for.
This role is a 1099 contractor role with a base hourly pay and commission of sales.
Key Responsibilities
Conduct sales consultations and discovery calls with leads from webinars, referrals, and inbound inquiries
Learn and communicate the nuances of WILA programs ( Jumpstart, Accelerate, Incubator+, and beyond) in a way that’s clear, honest, and value-driven
Qualify leads and guide them through the application and enrollment process
Maintain accurate records in CRM (HighLevel), update pipeline stages, and follow up with prospects consistently
Collaborate with the Marketing team on messaging, lead engagement, and campaign feedback
Help develop FAQs and sales enablement materials to streamline responses to common objections
Monitor sales KPIs and report weekly on conversion metrics, trends, and opportunities
Provide white-glove support to accepted students during their onboarding process
Stay informed about immigration industry trends and program updates to offer relevant insight during calls
What You Bring
2+ years experience in sales, admissions, or client enrollment (education, coaching, or legal industry preferred)
Strong communication skills — especially listening, reframing, and building trust
CRM experience (HighLevel preferred) and confidence working in a digital workspace
A people-first approach to sales — motivated by impact and alignment over pressure
Experience working with adult learners, first-gen professionals, or values-driven entrepreneurs
Bilingual (Spanish/English) strongly preferred
Bonus: knowledge of immigration topics and/or online education models
This Role Is for You If…
You’re energized by connecting with people and helping them say “yes” to their goals
You’re the kind of person who follows up with heart and holds space without pressure
You understand that great sales is about building clarity, not closing deals
You enjoy systems, scripts, and structure — but know when to pivot and lead with intuition
You believe that access to legal services can change lives — and want to be part of the movement
How to Apply (No Resume Yet!)
Send an email sharing your response to the following prompt:
“Why do you believe WILA’s work matters — and how would you help more people say yes to this opportunity?”
Also include a short story about a time you helped someone confidently commit to a service, program, or opportunity.
Include your DISC Score.
Email both to: support@wilaedu.com
Subject: In-House Sales Strategist – [Your Name]