Customer Success Manager

Awardspring; Chicago (IL); Hybrid; USD 70,000 - 110,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

401(k) match

Unlimited PTO

Parental leave

Job summary

AwardSpring is seeking a Customer Success Manager in Chicago to own customer health from onboarding to renewal and upsell. You will be the single point of contact, resolving requests, routing to Support/Product/AE, and escalating early when risk appears.

You will drive renewals, upsell add-ons, and run workshops to increase product adoption, with a strong emphasis on proactive communication and CRM hygiene in HubSpot. This hybrid role is based in Chicago with a mature, AI-enabled product suite.

Qualifications

• 2+ years in customer success or account management at a SaaS company.
• Ability to own renewals, upsell, and manage accounts end to end.
• Strong listening and questioning to understand customer needs and drive outcomes.

Responsibilities

• Spend 60% of your week with customers in live meetings, workshops, and best-practice sessions.
• Maintain tiered cadence: quarterly/monthly touchpoints per tier.
• Prepare for each meeting with a clear brief and objectives.
• After meetings, send a written recap with next steps within 24 hours and log it in HubSpot.
• Respond to customer emails within 4 business hours.
• Kick off renewals at least 6 months before contract end and issue service orders 60 days prior to auto-renewal deadlines.
• Own renewal and upsell from quote to signature, including terms and context for cross-sell opportunities.
• Listen for next product needs and coordinate with Account Executive when ready to close.
• Drive adoption and monitor fund utilization; identify accounts not using what they bought.
• Run customer workshops and webinars; share product updates to keep customers current.
• Route issues to Support/Product/AE while keeping HubSpot up to date in real time.
• Track metrics: customer meeting hours and product adoption; publish weekly and monthly NRU.

Skills

Customer Success

Account Management

SaaS

Communication

Tools

HubSpot

Job description

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.

About this role

You own the health of a book of AwardSpring customers, from the day Onboarding hands them to you live, through every renewal after that. Churn at AwardSpring 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 escalare 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.

How we work

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:

• 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.

What you'll do

• 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 HubSpot 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 AwardSpring 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 each one. Watch fund utilization too: money left unawarded is the first sign.
• Run workshops for your customers, and webinars once that program starts. Share product updates so your customers are current on every release.
• Solve what the platform already does before you escape. Then route cleanly: tickets to Support, feature requests to Product, cross-sell interest to an Account Executive.
• Keep HubSpot current the same day, every day, while we keep moving the CRM toward touchless.
• Know your numbers. Customer meeting hours and product adoption are published weekly, net revenue retention monthly.

Who you are

• You know the platform well enough to get a customer anything they need, as long as the product already supports it. You find the way before you file the ticket.
• You steer the account. You come to every meeting with a view on what the customer should do next, not only answers to their questions.
• You are an active listener, and your questions show you heard. Customers leave a meeting with you having learned something about their own program.
• You treat the renewal and the upsell as part of the relationship, not a separate sales call.
• You stay current. When a release ships, you know it before your customers ask.
• 2 or more years in customer success or account management at a SaaS company, or in a financial aid, advancement or foundation office. We care more about how well you know your customers' world than where you learned it.

What we're not looking for

• Someone who answers requests but never steers the account.
• Someone who escalates to Support what they could have solved by knowing the product.
• Someone who treats the renewal as paperwork.

How we'll measure you

We also watch, but don't measure: whether every account is current on its touch cadence, fund utilization, how often your customers advocate for us, and whether they are current on new releases.

1. Customer meeting hours per week. Completed meetings with someone from a customer account in your book. Workshops and best-practice sessions count. The bar is 60% of your week, about 24 hours.
2. Net revenue retention, trailing 12 months. Your accounts' recurring revenue today against 12 months ago, counting renewals, upsells, cross-sells, downgrades and churn. Cross-sell counts for you because you find it and hand it over.
3. Product adoption. The share of your accounts that actively use the features that matter most in every product they own.

On the AI part of this job

We will teach you our stack in your first month and check in at day 30. By then you are reading the account brief before every meeting, editing drafted follow-ups instead of writing from scratch, and checking every quote before it goes out. By day 90 we expect more: you have spotted a task you repeat and turned it into a skill or an automation the rest of the team can use. You do not need to arrive knowing how to build these. You do need to want to, and the CSMs who do best here reach for the model before they do a thing by hand.

How you advance

A year in, doing this very well looks like every account in your book adopting what it owns, net revenue retention above 100% because your upsells outpace your churn, and customers who send their peers to us.

• Senior CSM, with a larger and more strategic book of accounts.
• Customer Experience Engineer, if the part you love most is building the tools and automations that make the team faster.

Benefits

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

Hybrid, based in our West Loop / Fulton Market office in Chicago, three days a week. In-office presence is part of the job, with the specific schedule set with your manager.

How we hire

1. A 20-minute phone screen.
2. A 45-minute conversation with the hiring manager about renewals you have saved, customers you have lost, and expansions you have found.
3. A work sample: we send you an at-risk account ahead of time, you present a 15-minute save plan, role-play the call, and write the follow-up email.
4. A conversation with the Account Executives and Customer Experience team you would work with.
5. A conversation with our CEO.
6. References and an offer.

At least one interview is in person at our Chicago office.

AI in hiring

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 [e-mail] to request it. It will not disadvantage you.