Onboarding Specialist

Careers

Onboarding Specialist

Full-Time

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

Customer Experience

$55,000 - $60,000 / year

Based on experience

10% annual bonus opportunity, based on company performance

Award Spring 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 own launch. When an organization signs with us, you are the person who takes them from contract to live, and you own their success. That is the customer-facing half of the job, kickoff calls, training, and honest conversations about timelines, and the behind-the-scenes half, data imports, form and workflow configuration.

This is a Coach role  partner with institutions to drive results, and the results belong to them: an application cycle that opens on time, an advancement team that can finally see its donors, a department that stops running its process out of spreadsheets. Configuration is the means, not the point. The job is coaching an administrator from “we bought software” to “we changed how we work”.

Award Spring 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.

• Intellectual curiosity. When you don't know something, you go learn it instead of waiting to be taught.
• Agency. You act without waiting for permission. You take ownership of the problems in front of you and move on them decisively.
• Ambition. You want your work to matter. You are here for real impact, and you are willing to push past your own limits to make it.

We are a small, focused team on a mature, multi‑tenant platform. Nobody here has a narrow lane.

• Own onboarding and implementation projects end to end, from kickoff through go-live and handoff.
• Understand what the customer is actually trying to change about how they work, then sequence the rollout so they get there.
• Run your projects and timelines in a project management tool, current enough that anyone can pick up the status without asking you.
• Work closely with Support on testing and post‑launch readiness so nothing lands on them cold.
• Configure forms, workflows, conditional logic, and data integrations across whichever of our products the customer bought.
• Import and map customer data, then validate it before launch rather than after.
• Use AI tooling to take the repetitive work off your plate: data mapping and cleanup, configuration QA, first drafts of training materials and customer‑facing docs, meeting notes and follow‑ups. Then bring back what worked so the whole team gets faster.
• Deliver live training sessions for scholarship administrators and advancement teams, on the products they actually use.
• Host webinars for the broader customer base to train at scale.
• Build and run training materials against the priorities set by Customer Experience leadership.

• 1 to 3 years in onboarding, implementation, or support for a SaaS product.
• Strong organizational skills and real attention to detail.
• Comfortable with data. Excel and CSV work, mapping messy customer files, spotting the row that is going to break something.
• A clear and patient communicator.
• Accountable for timelines and outcomes without being chased.
• AI‑fluent in your own workflow, or ready to ramp up quickly.
• Genuinely curious about how a scholarship, financial aid, or advancement office spends its day, not just about our…