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 . This is a full-time job 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.

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

Compensation

• 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. $50k - $95k in total annual compensation (base + commission). Full health, dental, vision, and retirement benefits begin the day you transfer to the partner.

No tuition. No loans. No deferred-income agreement.

We're paid out of the hiring budget the partner was already going to spend — which means our incentive is to make you successful in the role!

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. No cost to you. You'll learn the fundamentals of B2B sales: outbound calls, email and LinkedIn outreach, objection handling, qualification, CRM and sales engagement tools (Salesforce or HubSpot, Outreach or Salesloft, ZoomInfo, LinkedIn Sales Navigator).

Days 11–100 — Paid Residency at a partner company. You'll work full-time at one of our partner companies as a W-2 employee of SV Academy. 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 — you take feedback and act on it
• Resilient — sales involves rejection, and you can keep going
• Strong written and spoken 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.

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.

Required Qualifications:

• English proficiency sufficient for professional work communication
• Permanently authorized to work in the United States without sponsorship
• Ability to attend evening sessions during the 2-week bootcamp

Preferred Qualifications:

• Completed Bachelors degree
• Experience in a customer-facing role such as retail, hospitality, customer support, fundraising, or account management
• Experience in a goal-driven role with measurable targets (quotas, KPIs, bookings, revenue, or activity metrics)
• Confident and engaging communicator
• Excited by ambitious goals and motivated by a high-performance environment

Benefits:

• Professional development through SV Academy's bootcamp and ongoing training
• Paid residency placement opportunity with high-growth employer partners at a SaaS organization
• Collaborative team environment focused on growth and mentorship
• Hybrid or on-site work environment in the Chicago area with opportunities for in-person collaboration
• Professional development and mentorship from experienced sales leaders
• Potential for full-time placement with partner companies upon successful completion of the program
• Access to a supportive alumni network and ongoing career resources
• Health insurance and retirement benefits aligned with industry norms for entry-level roles