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Mid-Market Customer Success Manager

Remote / Online - Candidates ideally in
Northern, Floyd County, Kentucky, USA
Listing for: Aiwyn
Full Time, Remote/Work from Home position
Listed on 2026-09-23
Job specializations:
  • Customer Service/HelpDesk
    Customer Success Management, Client Relationship Management, HelpDesk/Support
  • Business
    Customer Success Management, Client Relationship Management
Salary/Wage Range or Industry Benchmark: 90000 - 140000 USD Yearly USD 90000.00 140000.00 YEAR
Job Description & How to Apply Below
Location: Northern

Who is Aiwyn and what do we do?

Aiwyn is the first complete platform for modern accounting firms. Backed by top-tier investors like Bessemer, KKR, and Revolution, we’re one of the fastest-growing scale-up SaaS companies in the world. We build category-defining technology, and we’re doing it with world-class people, processes, and products.

To learn more, visit our website

What we are looking for:

An experienced Customer Success Manager to drive retention and growth within our strategic enterprise customer base. The ideal candidate has a proven track record in SaaS customer expansion and renewal processes, particularly with large-scale enterprise accounts, and excels in strategic customer engagements.

What you'll be doing:
  • Oversee customer onboarding, post-launch reviews, quarterly business reviews, and executive check-ins to ensure customer success and satisfaction.

  • Work closely with Enterprise customers to understand their business objectives and create a tailored success plan that delivers tangible outcomes.

  • Provide guidance to enterprise customers on adopting and maximizing the usage of our solutions, focusing on long-term retention, expansion, and advocacy.

  • Engage with the Customer Support Team to address customer inquiries, technical issues, and any other concerns.

  • Travel on-site to visit customers for executive check-in meetings

  • Collaborate on building and iterating on our renewals process to support our customers

  • Design and refine renewal playbooks, utilizing data insights to support customer health and drive revenue retention.

  • Collaborate with Sales and Customer Success Management to uncover and pursue expansion opportunities.

  • Work with Sales, Product, and Marketing to share industry best practices and drive the evolution of our platform.

What you'll need to be successful:
  • A minimum of 2 years in Customer Success, Renewal Management, or Account Management, with a focus on enterprise-level SaaS customers for at least 2 years.

  • Experience in early-stage startups with a willingness to embrace ambiguity and quickly adapt to change.

  • High EQ; adept at managing multiple stakeholder relationships.

  • Demonstrated success in increasing renewal rates and building effective renewal processes.

  • Ability to create and refine Customer Success playbooks and processes. Familiarity with Hub Spot or Salesforce is required.

  • Comfortable analyzing large data sets to identify trends and lead-indicators for customer health and risk mitigation.

  • Experience managing and expanding enterprise customer relationships, with strong negotiation skills and the ability to overcome objections.

  • A collaborative approach with innovative ideas, a sense of humor, and a passion for customer success.

  • Experience with Customer Success platforms like Gainsight or Churn Zero is a plus.

  • A self-motivated attitude with a willingness to go above and beyond to ensure customer success and satisfaction.

  • Travel up to 30% of the time.

  • Benefits and Perks:
    • The big-picture value proposition of this role is simple: join us, and you’ll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience.

    Other benefits include:

  • Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.

  • Remote, work-from-anywhere culture

  • Flexible PTO

  • World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.

  • Stock options - every Full Time Employee has ownership in Aiwyn's future…

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