Sales Development Representative

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

Sales Development Representative

Location: Chicago, West Loop, hybrid three days a week

Contract: Full-Time

Salary: $45,000 - $55,000 base

OTE: $80,000 - $90,000 OTE

Variable target: ~$35,000 variable target

Uncapped commission with accelerators

Who we are

AwardSpring is an established, growing SaaS company that partners with hundreds of colleges, universities, and foundations across the US and Canada to award scholarships and manage their donors. We complete the virtuous cycle of giving, getting, and giving again, on a mature, multi-tenant platform, with a small, focused team.

Our vision: to empower every institution to change students' lives. Our mission: we turn donor generosity into student opportunity. That is not wall art. It is the reason this job exists and it is what you will be selling.

About This Role

You build the top of our funnel. You pick the institutions, find the reason to call, and book first meetings that turn into real opportunities. Your meetings round-robin across our whole AE bench, so you are not carrying one rep's calendar, you are carrying the number.

This is a phone-first job at a company that has removed almost everything that usually keeps a rep off the phone. No hand-built lists, no sequences written from scratch, no call notes typed by hand. What is left is the part that actually matters: knowing who to call, why now, and what to say when they pick up.

There is a clear path forward. SDRs here move to AE or CSM in 9 to 15 months, and it is decided on the numbers rather than on a vibe.

How we work here

We are an AI-native company and that includes sales. You will not hand-build a list, write a sequence from scratch, or type a call note. Our research engine tells you which institutions have a reason to talk right now and why, enrolls them into sequences, and puts a one-page brief in front of you before every call. AwardSpringOS is your command center for account prioritization, institution research, and coaching. Nooks runs the dialing. Gong records and analyzes your calls. HubSpot is the system of record and it is current the same day, every day.

You will not be left to work this out alone. You get a weekly 1:1, a weekly call review with your manager, team training every two weeks, and a written ramp plan with your numbers on it from day one.

What that buys you is time on the phone and a real reason to be calling. What we expect in return is that you use it. If you have been quietly building your own prospecting workflow with AI on the side, because your last shop made you log into six tools and rebuild every sequence by hand, here that is the actual job.

What you'll do

• 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 than the people we find.
• Run short discovery and hand qualified opportunities to an AE.
• Keep HubSpot current the same day, every day.
• Review your own Gong calls and come to coaching with what you already noticed.

Who you are

• 0–2 years in outbound sales or a comparable high-activity role. SaaS helps, it is not required.
• Comfortable on the phone and unbothered by a no. You open cold, handle an objection, and get to a real question fast.
• You write a four-sentence email that gets a reply.
• Curious about how a financial aid office spends its day, not just about our product.
• Data-driven about your own performance. You know your connect rate without being asked.
• AI-fluent in your own workflow, or ready to be inside a month. You read the brief before the call and you do not retype what a model can draft.
• Coachable, organized, and competitive without being a lone wolf. The meetings you book get worked by someone else.

How we'll measure you

• 60 calls a day.
• 4 discovery meetings held a week.
• Pipeline created each month.

On the AI part of this job

We will teach you our stack in your first month and check in on it at day 30. By the time your ramp is complete, working this way is the expectation rather than a bonus. We expect you to learn on the job, not come knowing how to work AI native from day 1.

What we give you

Top-tier AI tooling with unlimited token budgets, and day-one access to the latest models as they ship. Uncapped commission with accelerators for top performers. Health, dental, and vision insurance, 401(k) match, unlimited PTO, and paid parental leave.

Our values

Lead with humanity. Genuine empathy for our team, our customers, and the students and donors they serve. That includes candor, saying the hard thing because you respect the person enough to say it.

Take smart risks. Urgency. Bold, informed bets before the picture is fully clear. Run the experiment instead of winning the debate.

Take pride in the process. Fast is the standard and thoughtfulness is non-negotiable. Eyes on the work you control, not the scoreboard.

Own the results. We measure everything. Accountability runs on data, not vibes, and we can tell the difference between an honest miss and a broken process.

Work location

Chicago, West Loop / Fulton Market office, hybrid three days a week.

Equal opportunity

AwardSpring is an equal opportunity employer and hires without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status. We're committed to an inclusive, harassment-free workplace.