Founding Customer Success Manager (Early-Stage)

At Apprentice, We help finance teams automate complex, recurring workflows using AI. Customers run their processes and describe them in real time, and our platform learns the workflow and converts it into automations they can manage going forward.

We’re early: live product, paying global enterprise customers, and growing demand. Delivering value still requires hands-on work across customers, product, and delivery.

We’re hiring a Customer Success Manager to own onboarding, delivery, and growth - working directly with customers and helping shape how this function scales.

What You'll Do

Own onboarding and value delivery

• Lead onboarding end-to-end for new customers and users
• Work directly with finance teams to drive adoption and define use cases
• Ensure automations are delivered and create measurable impact

Own execution

• Break down customer workflows into clear steps, identifying edge cases and exceptions
• Stay close to day-to-day usage and ensure automations work reliably in practice
• Coordinate with internal teams to move delivery forward
• Troubleshoot issues and remove blockers

Drive growth

• Build and maintain relationships with decision makers
• Identify expansion opportunities based on usage and outcomes
• Support renewals and value conversations
• Partner with Sales on POCs and trial conversions

Build the foundation

• Document processes and turn them into repeatable playbooks
• Contribute to how onboarding, adoption, and support scale

What We're Looking For

• 3-6 years in Customer Success, Implementation, or similar hands-on roles
• Experience in early-stage startups (Series A or earlier) 
• Passionate about working directly with customers on processes, data, and workflows
• Able to engage both business and technical stakeholders
• Strong analytical mindset - able to break down workflows, identify edge cases, and ensure automations are robust (not just working in ideal scenarios)
• Strong project management skills - able to scope work, prioritize, manage timelines, and drive multiple customer initiatives forward simultaneously
• Problem-solver with technical curiosity; comfortable understanding systems and driving solutions forward
• Clear communicator who builds credibility with decision-makers
• High ownership and ability to operate without heavy structure
• Ability to work in a dynamic and changing environment
• Fluent English

Nice to Have

• Experience with finance tools / CFO stack (ERP, payments, AP/AR, etc.)
• Background in fintech, SaaS, or workflow automation
• Accounting or finance background - familiarity with financial operations (AP/AR, reconciliations, payment cycles, month-end close),

What We Offer

• Direct ownership and impact on customers, product, and how the function is built
• Close work with founders, product, and engineering
• Growth opportunities as the company scales, based on performance