Customer Success Lead

Company Overview

Award Spring 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 Hub Spot 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 Hub Spot 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 Hub Spot + product usage data to flag at-risk accounts before they churn, replacing manual gut-check reviews.
• Lifecycle playbook automation — Multi-step Hub Spot 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…