Account Executive, Community Colleges

AwardSpring; Chicago (IL); Hybrid; USD 120,000 - 130,000; Full time

Benefits offered by this job

AI tooling of the highest level

Uncapped commission with accelerators

Competitive benefits: health, dental,

401(k) match

Job summary

AwardSpring is seeking an Account Executive for Community Colleges in Chicago on a hybrid basis or in-territory with written approval. You will own the region, manage a short sales cycle, and drive adoption across our platform for financial aid and advancement offices.

You will build pipeline, run discovery and demos, and close deals across four products, with uncapped commissions and a defined ramp. Expect travel 3–5 days monthly and active NASFAA conference involvement.

Qualifications

• 1–3 years closing SaaS or transactional B2B.
• Top performer in your current role.
• Outbound rhythm across a wide territory.
• Demo to the workflow, not the feature list.
• Close on a real timeline; sales cycles run ~quarterly.
• Curious about two-year community college operations and able to build your territory plan.
• AI-fluent in your workflow, or ready to learn quickly.

Responsibilities

• Build pipeline into your region through outbound and SDR-sourced meetings.
• Run the full cycle: discovery, demo, proposal, negotiation, close.
• Sell across four products at the first sale; cross-sell post-sale.
• Own handoff to implementation; align promises with delivery.
• Collaborate with customer success to surface cross-sell opportunities.
• Prioritize named accounts by size; mid-sized colleges convert best.
• Represent AwardSpring at NASFAA-affiliate conferences.
• Forecast using evidence; travel 3–5 days per month to events.

Skills

SaaS sales

Outbound sales

Deal closing

Territory planning

Tools

HubSpot

Gong

Job description

• Chicago hybrid, or in-territory with written approval

Careers

Account Executive, Community Colleges

• Full-Time
• Chicago hybrid, or in-territory with written approval
• Sales

• $65,000 - $75,000 base
• $120,000 - $130,000 OTE
• ~$55,000 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 own the community colleges in your region. Aid offices at these institutions are still running scholarship awards on spreadsheets, paper, and homegrown forms. Our platform helps them get more aid into more students' hands with far less administrative lift, and helps their foundation office raise and steward the dollars behind those awards.

Deals here move on a roughly 90 day cycle with a small buying group, and we have extremely satisfied customers in this segment with high renewal rates. By working through both Financial Aid and Advancement/Foundation, you’ll sell across our whole platform when we land, and also have the opportunity to cross-sell post sale.

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

• Build pipeline into your region through your own outbound plus SDR-sourced meetings.
• Run the full cycle: discovery, demo, proposal, negotiation, close.
• Sell across our four products at the first sale rather than coming back years later.
• Own the handoff into implementation. What you promise on the call becomes what the customer gets.
• Work with customer success to close cross-sell opportunities surfaced from existing customer relationships.
• Prioritize your named accounts by size. Mid-sized colleges convert best and behave differently from the small ones.
• Own your region's presence at NASFAA-affiliate (state and regional financial aid association) conferences.
• Forecast on evidence, not optimism.
• Travel 3 to 5 days a month to regional and NASFAA-affiliate events.

Who you are

• 1–3 years closing SaaS or transactional B2B.
• A top performer where you are now, and able to show it.
• You hold an outbound rhythm across a wide territory without being chased.
• You demo to the workflow, not to the feature list.
• You close on a real timeline. Our sales cycle runs about a quarter
• Curious about the operational reality of a two-year community college, and able to build your own territory plan without being handed one.
• AI-fluent in your own workflow, or ready to be inside a month. We coach you to our standard, and holding it is a requirement once your ramp is complete. We expect you to learn on the job, not come knowing how to work AI native from day 1.

How we'll measure you

You get the actual figures and your ramp in week one, and we expect new team members to be performing at full speed after 90 days.

• Customer and prospect meetings held each week.
• Pipeline created each month.
• Closed-won pipeline each quarter.

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 hybrid, three days a week in the West Loop, or living inside your assigned region with written approval from the President. The in-territory arrangement carries a floor of 10 in-person customer or prospect meetings a month, roughly 8 field days.

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.