Inside Sales Representative (Chicago, IL)
The Inside Sales Representative role at Confidential Client offers a full-time position combining free sales training and a paid residency at partner companies, focusing on B2B sales activities such as outbound prospecting, lead qualification, and scheduling meetings. This position provides a clear career path into tech sales with mentorship, hands-on experience, and potential full-time placement at high-growth SaaS organizations, primarily based in a hybrid work environment in Chicago.
About Careertakes
👉 Important disclosure: Careertakes is a third-party recruiting platform supporting this hiring process. If selected, you will be employed directly by our client, a workforce-development & tech sales training organization serving SaaS, AI, fintech, cybersecurity, and other high-growth tech verticals.
Applicants for this role may also receive access to additional matched opportunities through the Careertakes platform.
What You’ll Do
Confidential Client is recruiting entry‑level Inside Sales Representatives for a paid training + residency program based in the Schiller Park / Chicago area. This is a full-time, outcomes-focused pathway into B2B sales with hands-on coaching and a clear route to long-term placement at high-growth partner companies.
- Complete an instructor‑led, no‑cost sales bootcamp (live evenings on Zoom).
- Work a paid residency (W‑2) at a partner company: outbound prospecting by phone, email and LinkedIn; qualify inbound leads; schedule discovery meetings for Account Executives.
- Track activity and outcomes in CRM and sales engagement tools (Salesforce or HubSpot, Outreach or Salesloft).
- Accept daily coaching, iterate on outreach, and meet measurable activity and conversion goals.
- Transition to the partner company’s payroll upon successful completion of the program.
How the 100 Days Work
Days 1–10 — Free sales training (live, instructor‑led).
- Monday–Thursday evenings (6–9 pm ET or PT) on Zoom.
- Core skills: outbound calling, email & LinkedIn outreach, objection handling, qualification, and CRM/sales engagement basics.
Days 11–100 — Paid Residency.
- Full‑time W‑2 placement embedded at a partner company in the Chicago area.
- Real sales work with daily coaching from Confidential Client mentors and partner sales leadership.
Day 100 onward — Transfer to partner payroll for full-time placement (when eligible).
Compensation & Benefits
- Paid Residency: $2,500/month base during Days 11–100 + 100% of commissions earned during the residency.
- Post-transfer total annual compensation (base + commission): $50,000 – $95,000 (typical range).
- Benefits begin when you transfer to the partner (health, dental, vision, retirement) per partner policy.
- Professional development, coaching, alumni network, and strong placement pipeline with SaaS/tech partners.
Who We’re Looking For
Required
- English proficiency sufficient for professional work communication.
- Permanently authorized to work in the United States without sponsorship.
- Ability to attend evening sessions during the initial training (two‑week bootcamp).
Preferred
- Completed bachelor’s degree (preferred but not required).
- Experience in customer‑facing roles (retail, hospitality, customer service, fundraising, fitness instruction, teaching, etc.).
- Experience with measurable targets (quotas, KPIs, bookings, revenue, or activity metrics).
- Comfortable on the phone, coachable, resilient, and an engaging communicator.
This role is ideal for candidates motivated by clear goals, rapid development, and a pipeline into high-growth tech sales roles.
Location & Work Model
- Primary location: Schiller Park, IL (Chicago area).
- Hybrid or on-site residency placements depending on partner needs and role requirements. Travel to partner sites in the Chicago area may be required.
Selection Process
- Apply through the Careertakes posting (brief application).
- Confidential Client will respond promptly — typical reply within 2 business days.
- If you’re a fit: a 20‑minute intro call, then cohort placement. Cohorts begin frequently and are limited in size — early application improves placement chances.
Equal Opportunity & Hiring Transparency
Careertakes and our client are Equal Opportunity Employers committed to building a diverse and inclusive workforce. We prohibit discrimination or harassment of any kind. To support a fair and efficient hiring process, AI tools may be used to assist with application review or resume screening. These tools do not replace human decision-making. Final hiring decisions are made by people.
If you have questions about how your data is used, please contact us directly.
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