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Mid-Market Customer Success Manager

Aiwyn - Remote - Remote - posted 2026-08-04

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Aiwyn is a rapidly growing SaaS platform serving modern accounting firms, backed by top-tier investors including Bessemer, KKR, and Revolution. As a Customer Success Manager, you will drive retention and expansion within our strategic enterprise customer base, managing the full lifecycle of high-value accounts. Key responsibilities include overseeing customer onboarding, conducting quarterly business reviews and executive check-ins, and developing tailored success plans aligned with customer business objectives. You'll guide enterprise customers in maximizing platform adoption and usage, collaborate with support teams to resolve issues, and work cross-functionally with sales and product teams to identify expansion opportunities. You'll also design and refine renewal playbooks using data insights to support customer health and drive revenue retention. The role requires up to 30% travel for on-site customer visits. You bring a minimum of 2 years in customer success, renewal management, or account management focused on enterprise SaaS. You have startup experience and comfort with ambiguity, strong emotional intelligence for managing multiple stakeholder relationships, and a proven track record increasing renewal rates. You're proficient with HubSpot or Salesforce, skilled at analyzing data to identify customer health trends and risks, and experienced managing and expanding enterprise relationships with strong negotiation abilities. Familiarity with customer success platforms like Gainsight or ChurnZero is a plus. You're self-motivated, collaborative, and passionate about customer success. Aiwyn offers competitive compensation, remote work-from-anywhere flexibility, flexible PTO, comprehensive health benefits (medical, vision, dental, HSA/FSA, mental health), stock options for all full-time employees, 401(k) matching, and an annual $1,000 adventure travel stipend.

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