Customer Success Lead

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.

• 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.

This isn't a "someday" wishlist — these are real projects you'll lead in your first year:

• Automated customer health scoring — Using HubSpot + product usage data to flag at-risk accounts before they churn, replacing manual gut-check reviews.
• Lifecycle playbook automation — Multi-step HubSpot sequences that trigger the right outreach at the right time: post-onboarding adoption nudges, mid-cycle optimization prompts, pre-renewal engagement sequences.
• AI-powered knowledge base strategy — Partnering with Support to identify the highest-deflection-rate topics (How-To/Training tickets are up 48% YoY) and building the KB content that lets AI agents handle them.
• Renewal forecasting and pipeline visibility — Automated dashboards and alerts so no renewal sneaks up on the team and leadership has real-time visibility into retention risk.
• Scalable customer touchpoint model — Designing which customer interactions should be 1:1 human, which should be 1:many automated, and which should be AI-assisted — then building the infrastructure for each.

• 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

• 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)

• Base salary: $85,000 – $100,000 (commensurate with experience)
• Variable compensation: Up to $40,000, tied to net revenue retention and expansion targets
• OTE: $125,000-140,00

• ACTION — We have a bias for action. Small team, big ambition. We own outcomes, not just activities.
• DETERMINATION — We find a way. When the playbook doesn't exist, we write it. When the tool doesn't exist, we build it.
• HUMANITY — We're human first. Empathy and genuine care for our customers and each other aren't optional — they're foundational.
• IMPROVEMENT — We keep improving. Every day, a little better. We tinker, measure, iterate, and share what we learn.

• Health, dental, and vision insurance
• 401(k) with matching contributions
• Unlimited PTO and paid sick days
• 20 company holidays
• Generous parental leave
• Hybrid work (3 days in-office at our Chicago WeWork, West Loop)

AwardSpring is at an inflection point. We're growing our customer base, launching a new product lines, and investing heavily in AI and automation across the business. The Customer Success Lead will shape how we scale customer relationships — not by adding headcount linearly, but by building smarter systems that let a small, sharp team deliver outsized results.

If you're the kind of person who reads about a new AI tool and immediately thinks "how could I use this for my customers?" — we want to talk to you.

AwardSpring is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We encourage candidates of all backgrounds to apply.