AwardSpring

Customer Success Lead

AwardSpring

full-time

Posted on:

Location Type: Hybrid

Location: Chicago • Illinois • United States

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Salary

💰 $85,000 - $100,000 per year

Job Level

Senior

About the role

  • 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.

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.
Benefits
  • 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)
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
customer successaccount managementCRM automationdata-driven prioritizationcustomer health scoringlifecycle automationfeature adoptionnet revenue retentionrenewalsexpansion revenue
Soft Skills
coachingmentoringcommunicationanalytical instinctscustomer advocacystrategic thinkingproblem-solvingteam collaborationleadershipcustomer engagement