Customer Success Lead

AwardSpring•Chicago, IL

6d•$85,000 - $100,000•Hybrid

About The Position

AwardSpring is a fast-growing SaaS company on a mission to make it easy for students to apply for and receive scholarship money — and easy for institutions to deliver it. We work with over 600 colleges, universities, and foundations across North America, and we're expanding into donor management to help advancement teams do more with less. We're a small team with an outsized impact. Every feature we ship, every workflow we automate, and every customer we retain puts real dollars in the hands of real students. If that sounds like work worth doing, keep reading. We're also a company going AI-native — not as a buzzword, but as an operating philosophy. We build internal AI tools, automate repetitive processes, and expect every team member to bring curiosity about what technology can do for their function. Our Customer Success team is no exception. We're looking for a Customer Success Lead who can do two things at once: build authentic, trust-based relationships with higher education customers, and build the systems and automations that let a lean team punch above its weight. This is a player/coach role. You'll manage a small team of CSMs (1-2 direct reports) while personally owning a book of ~200 accounts. You'll drive renewals, identify expansion opportunities, and coach your team through complex customer situations. But here's what makes this role different: we want someone who sees repetitive work as a problem to solve, not a task to endure. You'll design HubSpot workflows, experiment with AI-powered customer health scoring, shape our knowledge base strategy, and help us figure out which customer touchpoints should be automated and which demand a human voice. If you'd rather build a workflow than repeat a task — and you believe great CS is equal parts empathy and engineering — this role was built for you.

Requirements

4+ years in Customer Success, Account Management, or a related customer-facing role in B2B SaaS
1+ year of people management experience (direct reports, not just mentorship)
Demonstrated experience with CRM automation (HubSpot strongly preferred — workflows, sequences, deal pipelines)
Track record of driving net revenue retention, renewals, or expansion in a recurring revenue business
Strong analytical instincts — you look at data before making decisions and you're comfortable in dashboards, spreadsheets, or BI tools
Excellent communication skills — you can run a strategic business review with a VP and troubleshoot a configuration question in the same afternoon
Comfortable working in a small, fast-moving team where your scope will expand with the company

Nice To Haves

Experience in higher education, edtech, or nonprofit/advancement technology
Hands-on experience with AI tools (ChatGPT, Claude, Copilot, or similar) in a professional workflow — not just awareness, actual daily use
Experience building or managing a knowledge base, help center, or self-service content program
Familiarity with customer health scoring frameworks (Gainsight, ChurnZero, Vitally, or custom-built)
You've automated something meaningful in a prior role — a reporting workflow, a renewal sequence, a triage process — and you can tell us about it
Exposure to Zendesk, Intercom, or other support platforms (our CSMs collaborate closely with CX/Support)

Responsibilities

Own customer outcomes.
Manage a personal book of ~200 accounts.
Drive adoption, renewals, and expansion revenue across scholarship management and donor management product lines.
Lead and develop the CSM team.
Coach, mentor, and manage 1 CSM, with intent to expand as the company grows.
Run 1:1s, build competency frameworks, and set the bar for customer engagement quality.
Drive net revenue retention.
Own the NRR target for the CS org.
Identify at-risk accounts early, run the renewal risk playbook, and personally handle high-stakes renewal conversations.
Spot and activate expansion opportunities.
Identify cross-sell candidates, generate qualified introductions, and partner with Sales on upsell motions.
Build the customer health model.
Define and instrument customer health scoring using login data, feature adoption, support interactions, NPS, and scholarship cycle position.
Move from gut feel to data-driven prioritization.
Design and optimize lifecycle automations.
Build HubSpot sequences for onboarding, adoption check-ins, renewal prep, and expansion outreach.
Decide what gets automated vs. what stays personal.
Be the customer voice internally.
Surface product feedback, recurring pain points, and feature requests to Product and Engineering.
Translate customer patterns into actionable insights.
Cultivate customer advocacy.
Build a referral pipeline, develop case studies and testimonials, and grow the customer community.