Customer Success Manager

Location:

Chicago, West Loop, hybrid three days a week

Role:
Customer Experience

• $65,000 - $75,000 base
• $90,000 - $100,000 OTE
• ~$25,000 variable target, paid quarterly on net revenue retention

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 the health of a book of Award Spring customers, from the day Onboarding hands them to you live, through every renewal after that. Churn at Award Spring starts about 12 months before a renewal, not in the renewal meeting. So this job is customer health, not renewal paperwork: customers who are current on the product, using every feature that would help them, and singing our praises.

You are the customer's one point of contact. Customers bring their questions and requests straight to you. You solve them, or you route them: tickets to Support, feature requests to Product, and interest in a different standalone product to an Account Executive. When an account is at risk, you escalate early and bring in the right leader, and you keep the relationship and the renewal the whole way through.

You own the renewal and the upsell, from quote to signature, and you sell add-ons like SpringIQ and SpringAPIs within the product your customer already uses. You teach: you run workshops with customers, share product updates and consult on best practices, because a customer who knows the product uses more of it.

Your time goes where the outcome is decided. The account brief is pulled for you before each meeting, follow-ups are drafted for you, meeting outcomes log themselves, and every deal is checked before it goes out. What is left is the part that decides whether an account renews and grows: deciding what the meeting is for, the conversation itself, and knowing the platform well enough to solve what the customer needs.

As the machine takes more of the work, your book grows, and you carry more customers than a CSM at a company that has not rebuilt this way.

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.

• Spend 60% of your week with customers, about 24 hours: live meetings, workshops and best-practice sessions.
• Keep every account on its tier's cadence. Top tier: a meeting every quarter and a personal email every month. Middle tier: a meeting every year and a personal email every month. Smallest tier: the monthly automated touch.
• Prepare for every meeting. The brief is pulled for you. Read it, sharpen it, and walk in knowing what the meeting is for.
• After every meeting, send the customer a written recap with a dated next step within 24 hours, and log it in Hub Spot the same day.
• Reply to every customer email within 4 business hours, even if the first reply is "I'm on it, here's when you'll hear back."
• Start every renewal at least 6 months before the contract ends, and have the service order out by 60 days before the auto-renewal cancellation deadline.
• Own the renewal and upsell from quote to signature. The quote and service order are drafted for you and checked before they go out; you decide the terms and send it.
• Own the negotiation. Our pricing guardrails tell you where you stand on every quote. When a customer needs something outside them, work it out with the Customer Success Lead and the CEO.
• Listen for the next product in every conversation. You are not hunting for cross-sell; you are asking the questions that show where another Award Spring product would help. When it would, hand it to the Account Executive with the context they need to close it.
• Drive adoption in every account. Know which of your accounts are not using what they bought, and why, and have a plan for…