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Awardspring is seeking a Technical Solutions Engineer in Chicago to bridge sales and engineering for higher-education clients. You will walk financial aid and IT leaders through how AwardSpring enables award processing, reviews, and reporting on a modern AI-native platform.
You’ll drive technical discovery, demos, and security reviews while coordinating with onboarding teams for a clear scope. The role emphasizes live conversations with prospects and customers, deep product knowledge, and the
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.
You are the technical voice on AwardSpring's calls. You know each product in the platform at the deepest level, and you use that to show a prospect or customer how AwardSpring can be the solution for the work they need to manage. When a Vice President of Financial Aid wants to see how her scholarship process would actually run, you show her. When there's a better way to get there than the one she asked about, you suggest it and offer alternatives.
You are ready to speak with all of the functional and technical teams in an institution. You can walk a financial aid administrator through how awarding, reviews and reporting would work for her office. Then you can turn to the IT team and talk integrations, SSO and data in their language. You know when a deal needs those stakeholders, and you know how to bring them in.
Most of your week (at least 60%) is live conversation, about 80% with prospective customers and 20% with current customers. Account Executives bring you in for technical discovery, demos built around what this institution needs, IT and security calls, and the technical and security sections of RFPs. Customer Success Managers invite you in for a setup that needs deep technical work, or an upsell that needs a technical answer.
You help with the transition of technical items between Sales and Onboarding. What you scope with the customer is what our Onboarding Specialists build. So you don't overpromise. When something needs a clearer answer before we commit to it, you bring in the right people inside AwardSpring first, and you write down what we agreed to.
You don't carry an individual sales target, but your bonus is earned on the outcome of your work. You're on the calls that decide whether we win, retain, and expand our business. You win when the team does.
The mechanical work around the call is handled for you: account briefs before a call, call recaps, first drafts of security questionnaires, and demo sites with sample data. What's left is the part that decides the deal: reading the room, knowing what fits, and earning the trust of the person who has to sign off on us.
AwardSpring is an AI-native company. Nearly 100% of the code in our product is AI-generated, and every team here operates on the same principle: routine work gets delegated to AI so people spend their hours on the problems that actually need judgment.
We hire for three things:
We are a small, focused team on a mature, multi-tenant platform. Nobody here has a narrow lane.
We'll teach you our stack in your first month and check in on it at day 30. By the end of your ramp, working this way is the expectation. You don't brief yourself by hand, write recaps from scratch, or start a security questionnaire from a blank page. You do need to judge what the tools draft, because your name is on what we commit to. The people who do best here reach for the model first and save their own hours for the customer.
A year in, doing this well means technical questions have a clear owner, and it isn't leadership. Onboarding starts every project with a clear technical plan, security reviews have someone who can speak to them, Account Executives carry more of the common questions on their own, and product hears from the field through you. From there:
Health, dental, and vision insurance, 401(k) match, unlimited PTO, and paid parental leave.
Hybrid, based in our West Loop / Fulton Market office in Chicago, three days a week. Remote is open for a strong candidate.
We use AI tools to assist in screening applications and assessing fit. Final hiring decisions are made by humans. Prefer a review without AI assistance? Email our hiring team at careers@awardspring.com to request it. It will not disadvantage you.