Inside Sales Representative (Chicago, IL)

Inside Sales Representative (Chicago, IL)

You don't pay us. We pay you.

SV Academy is hiring Inside Sales Representatives . Free sales training, a 90-day paid Residency at $2,500/month plus 100% commission, then transfer to a partner company's payroll at their salary, commission, and benefits structure.

No tuition. No loans. No deferred-income agreement. We're paid out of the hiring budget the partner was already going to spend — which is why this costs you nothing.

Cohorts begin every week and are limited to 25 Residents. Apply early to be considered for the next available start date.

Compensation at Each Stage

• Days 1–10 — Free sales training. No tuition, no fee, no debt. Live, instructor-led training on Zoom, Monday through Thursday, 6–9 pm (ET or PT).
• Days 11–100 — Paid Residency. $2,500/month base + 100% of the commissions you earn. You'll be a W-2 employee of SV Academy, embedded at a partner company.
• Day 100 onward — Transfer to the partner's payroll. $50,000 - $85,000 in total annual compensation (base + commission). Full health, dental, vision, and retirement benefits begin the day you transfer.

How the 100 Days Work

Days 1–10 — Free sales training. Ten days of live, instructor-led training. Monday through Thursday, 6–9 pm (ET or PT), on Zoom. You'll learn the fundamentals of B2B sales: outbound calls, email and LinkedIn outreach, objection handling, qualification, and the tools used by modern SDRs (Salesforce or HubSpot, Outreach or Salesloft, ZoomInfo, LinkedIn Sales Navigator).

Days 11–100 — Paid Residency at a partner company. You'll work full-time as a W-2 employee of SV Academy at one of our partner companies. Real sales work: outbound prospecting via phone, email, and LinkedIn; qualifying inbound leads; scheduling discovery meetings for Account Executives. You'll get daily coaching from an SV Academy mentor and from the partner's sales leadership.

Day 100 — Transfer to the partner. Successful Residents transfer directly onto the partner's payroll at the compensation above, with full benefits starting that day.

About SV Academy

Since 2017, we've placed more than 6,000 people into full-time tech sales careers and worked with 400+ employer partners across SaaS, AI, fintech, cybersecurity, and other high-growth verticals.

Led by CEO Michael Colonnese, a 15+ year veteran of workforce development focused on building debt-free pathways into tech careers.

Our partners pay us. You don't. That's the entire business model.

Who Tends to Succeed Here

No prior sales experience required. We hire people who are competitive and motivated by clear goals, comfortable on the phone (including cold calls), coachable, resilient, and strong communicators.

If you've worked in retail, hospitality, customer service, fundraising, fitness instruction, teaching, or any role where you spent your day talking to people and meeting goals — you already have the foundation to be excellent at this.

• Full-time availability during the 90-day residency
• Permanent legal authorization to work in the United States without sponsorship
• Strong written and verbal English communication
• Available for evening training sessions (Mon–Thu, 6–9 pm ET or PT) during the first 2 weeks
• Located in or able to reliably commute to the partner site in Chicago

What Happens After You Apply

1. Apply through this posting — takes about 3 minutes.
2. We respond within 2 business days. If you're a fit, we'll set up a 20-minute intro call.
3. Cohort placement. If you move forward, we'll match you with a partner company and a start date. Cohorts begin every Monday and are limited to 25 Residents — apply early for priority consideration.

Apply today. The next cohort starts soon and spots fill on a first-reviewed basis.