Aiwyn

Aiwyn

AI-powered platform automating accounting workflows

Mid-Market Customer Success Manager

Full-Time
No salary listed
Junior, Mid
Remote in USA
Hybrid

Remote within the United States, with travel to customer sites up to 30% of the time.

About the job

Requirements
  • At least 2 years of experience in Customer Success, Renewal Management, or Account Management, including at least 2 years focused on enterprise-level software-as-a-service customers.
  • Experience in early-stage startups and willingness to embrace ambiguity and adapt quickly to change.
  • Ability to manage multiple stakeholder relationships.
  • Demonstrated success increasing renewal rates and building effective renewal processes.
  • Ability to create and refine Customer Success playbooks and processes.
  • Familiarity with HubSpot or Salesforce is required.
  • Ability to analyze large data sets to identify trends and leading indicators for customer health and risk mitigation.
  • Experience managing and expanding enterprise customer relationships, with negotiation skills and the ability to overcome objections.
  • Willingness to travel up to 30% of the time.
Responsibilities
  • Oversee customer onboarding, post-launch reviews, quarterly business reviews, and executive check-ins to ensure customer success and satisfaction.
  • Work with enterprise customers to understand their business objectives and create tailored success plans that deliver tangible outcomes.
  • Guide enterprise customers in adopting and maximizing the use of the company's solutions, focusing on long-term retention, expansion, and advocacy.
  • Engage with the Customer Support Team to address customer inquiries, technical issues, and other concerns.
  • Travel on-site to visit customers for executive check-in meetings.
  • Collaborate on building and iterating the renewals process to support customers.
  • Design and refine renewal playbooks, using data insights to support customer health and drive revenue retention.
  • Collaborate with Sales and Customer Success Management to identify and pursue expansion opportunities.
  • Work with Sales, Product, and Marketing to share industry best practices and drive the evolution of the platform.
Desired Qualifications
  • Experience with Customer Success platforms such as Gainsight or ChurnZero.

About the company

Aiwyn provides an AI-powered, all-in-one platform for accounting firms that consolidates and automates the revenue cycle. Its product suite includes Aiwyn Payments, Aiwyn Practice, Aiwyn Experience, and Aiwyn Tax, integrating with existing practice management systems and CRMs to reduce manual data entry. It targets mid-size to large CPA firms with a B2B model, aiming to replace multiple disconnected tools with a single system for firm-wide visibility and streamlined work-to-cash. Backed by $127M from investors like KKR, Bessemer Venture Partners, and Revolution Ventures, growth includes acquisitions of Taxa and Digilence; the goal is to improve efficiency and client service in accounting firms.

Company Size

51-200

Company Stage

Late Stage VC

Total Funding

$127M

Headquarters

Charlotte, North Carolina

Founded

2020

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Simplify's Take

What believers are saying

  • April 2026 Claude integration opens distribution to firms already using Anthropic tools.
  • December 2025 tax pilot and 900-plus firms show demand beyond billing automation.
  • Withum’s unified portal launch in 2026 proves larger firms buy Aiwyn’s platform.

What critics are saying

  • January 2026 layoffs cut 35% of staff, exposing execution strain.
  • Intuit and Thomson Reuters own accounting workflows, squeezing Aiwyn’s platform expansion.
  • Three acquisitions since 2025 increase integration risk and distract engineering through 2026.

What makes Aiwyn unique

  • Aiwyn unifies payments, practice, client experience, and tax into one accounting workflow.
  • April 2026 Anthropic Connector makes Aiwyn Tax accessible inside Claude.
  • Aiwyn Tax uses Column Tax’s engine, validated on over one million returns.

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Benefits

Remote Work Options

Unlimited Paid Time Off

Health Insurance

Dental Insurance

Vision Insurance

Mental Health Support

401(k) Company Match

Stock Options

Employee Discounts

Growth & Insights and Company News

Headcount

6 month growth

↓ -2%

1 year growth

↑ 1%

2 year growth

↑ 0%
PR Newswire
Apr 13th, 2026
Aiwyn joins Anthropic's Claude ecosystem with verified tax calculation engine

Aiwyn has joined Anthropic's Claude Connector ecosystem, integrating its AI-native tax calculation engine into Claude's platform. The partnership enables users to run 1040 calculations, perform scenario analysis and evaluate tax outcomes in real time directly within Claude. Founded in 2020, Aiwyn has processed over one million real-world 1040 returns and developed TaxCalcBench, a framework for validating calculation accuracy. The company's platform combines billing automation, client collaboration tools and tax calculation capabilities, enhanced by its December 2025 acquisition of Column Tax. The connector is now live at claude.com/connectors/aiwyn-tax. Aiwyn serves over 900 accounting firms and is backed by investors including KKR and Bessemer Venture Partners. The company plans to expand its tax engine coverage and deepen ecosystem integrations.

PR Newswire
Mar 30th, 2026
Withum and Aiwyn launch unified client portal to streamline professional services engagement

Withum, a top 25 accounting firm, has partnered with technology company Aiwyn to launch Aiwyn Experience, a unified client portal designed to streamline service delivery and client engagement for professional services firms. The platform consolidates traditionally disconnected client-facing tools into a single system, handling request intake, document exchange, deliverables and payment. Withum collaborated with Aiwyn to develop the custom-branded solution, which integrates seamlessly with existing technology through modular architecture and open APIs. According to Aiwyn research, 76% of accounting firms rate client experience as their top priority. The platform aims to address the gap between client expectations and disparate tools firms traditionally use, reducing manual coordination and allowing teams to focus on higher-value work whilst supporting scalable growth.

CPA Practice Advisor
May 8th, 2025
Aiwyn Acquires Taxa, Launches Aiwyn Tax

Aiwyn, based in Charlotte, NC, has acquired Taxa, rebranding it as Aiwyn Tax, to enhance its tax capabilities with AI-driven solutions. Taxa's founder, Levi Morehouse, joins Aiwyn as president. Aiwyn also acquired Digilence to integrate its automation technology. The new Aiwyn platform includes Aiwyn Payments, Practice, Experience, and Tax. Last December, Aiwyn secured $113 million in funding led by KKR and Bessemer Venture Partners.

Intelligence360 News
Jan 8th, 2025
Aiwyn Secures $113M Funding from KKR

Aiwyn has secured $113 million in funding from KKR and Bessemer Venture Partners to enhance firm operations and tax technology for CPA firms. The investment will support the development of a comprehensive practice management platform and a universal client experience portal. Aiwyn aims to integrate AI and cloud technologies to improve client experiences and streamline operations for CPA firms.

InfoTechLead
Dec 22nd, 2024
Aiwyn Raises $113M for CPA Tech

Aiwyn, a tech provider for CPA firms, raised $113 million in a funding round led by KKR and Bessemer Venture Partners. The funds will expand Aiwyn’s payment and collection tools into a full practice management platform and accelerate AI-driven cloud technologies and a tax solution.