Sales Development Representative (Chicago)
About the Role
SV Academy is hiring Sales Development Representatives for a full-time role that includes free sales training, a 90-day paid Residency at a partner company, and a clear path to a long-term sales role at one of our 400+ partner companies.
Compensation
- Days 1-10: Free sales training. No tuition, no fee, no debt.
- Days 11-100: Paid Residency. $2,500/month base + 100% of the commissions you earn as a W-2 employee of SV Academy.
- Day 100 onward: Transfer to the partner's payroll with $50k - $85k in total annual compensation (base + commission) and full health, dental, vision, and retirement benefits.
How the 100 Days Work
- Days 1-10: Free, live, instructor-led training on Zoom, Monday through Thursday, 6-9 pm (ET or PT). Learn B2B sales fundamentals: outbound calls, email and LinkedIn outreach, objection handling, qualification, and CRM tools (Salesforce/HubSpot, Outreach/Salesloft, ZoomInfo, LinkedIn Sales Navigator).
- Days 11-100: Paid Residency at a partner company. Full-time sales work: outbound prospecting, qualifying leads, scheduling meetings. Receive daily coaching from SV Academy mentors and partner sales leadership.
- Day 100: Transfer to the partner's payroll with full benefits.
About SV Academy
Since 2017, SV Academy has placed over 6,000 people into full-time tech sales careers, partnering with 400+ companies in SaaS, AI, fintech, cybersecurity, and other high-growth sectors. Led by CEO Michael Colonnese, we focus on debt-free pathways into tech careers. Our partners pay us, so there’s no cost to you.
Who Tends to Succeed Here
No prior sales experience required. We look for candidates who are:
- Competitive and goal-oriented
- Comfortable with phone communication, including cold calls
- Coachable and resilient
- Strong written and spoken communicators
Experience in retail, hospitality, customer service, fundraising, fitness, teaching, or similar roles is a strong foundation for success.
Application Process
- Apply through this posting (3 minutes)
- Receive a response within 2 business days
- If selected, participate in a 20-minute intro call
- Get matched with a partner company and start date (cohorts begin every Monday, limited to 25 Residents)
Requirements
Required Qualifications:
- English proficiency for professional communication
- Permanently authorized to work in the U.S. without sponsorship
Preferred Qualifications:
- Completed Bachelor's degree
- Experience in customer-facing roles (retail, hospitality, customer support, fundraising, account management)
- Experience in goal-driven roles with measurable targets
- Ability to attend evening sessions during the 2-week bootcamp
- Confident and engaging communication skills
- Motivated by ambitious goals and high-performance environments
Benefits
- Comprehensive 2-week online bootcamp training
- Paid 3-month residency with an employer partner
- Hybrid work environment
- Exposure to leading technology companies and sales teams
- Professional development and mentorship opportunities
- Supportive community and network of peers