AI-Driven SDR: High-Impact Prospecting & Fast Ramp

AwardSpring; West Chicago (IL); Hybrid; USD 45,000 - 55,000; Full time

Benefits offered by this job

Uncapped commission with accelerators

Health insurance

Dental insurance

Vision insurance

401(k) match

Unlimited PTO

Paid parental leave

Job summary

AwardSpring is seeking a Sales Development Representative in Chicago, West Loop, a hybrid role three days a week. You will own outbound prospecting into higher-education institutions, book first meetings, and hand opportunities to an AE.

Frontline phone-first approach with AI-assisted workflows and a fast ramp plan. You'll join a data-driven team measured by calls, discovery meetings, and pipeline growth, with uncapped commissions and strong onboarding.

Qualifications

• 0–2 years in outbound sales or a comparable high-activity role.
• Comfortable on the phone and unbothered by a no.
• Writes a four-sentence email that gets a reply.
• Curious about how a financial aid office spends its day.
• Data-driven about performance; knows own connect rate.
• AI-fluent in your own workflow or ready to be inside a month.
• Coachable, organized, and competitive; meetings booked get worked by someone else.

Responsibilities

• Own outbound into your accounts across phone, email, and LinkedIn.
• Use our research signal to decide who to call and why now, then let the sequence engine handle enrollment.
• Answer inbound the same day; the people who find us convert better.
• Run short discovery and hand qualified opportunities to an AE.
• Keep HubSpot current the same day, every day.
• Review your Gong calls and bring insights to coaching.

Skills

Outbound sales

Phone skills

Email outreach

Data-driven

AI workflow familiarity

Tools

HubSpot

Gong

AwardSpringOS

Nooks

Job description

AwardSpring is seeking a Sales Development Representative in Chicago, West Loop, a hybrid role three days a week. You will own outbound prospecting into higher-education institutions, book first meetings, and hand opportunities to an AE.

Frontline phone-first approach with AI-assisted workflows and a fast ramp plan. You'll join a data-driven team measured by calls, discovery meetings, and pipeline growth, with uncapped commissions and strong onboarding.