Customer Success Manager

Customer Success Manager - Remote (US)

About Wholesail (www.paywholesail.com)

About Wholesail

Wholesail (www.paywholesail.com) is building the financial network for wholesale trade — a $55 trillion global market that still runs on manual invoices, paper checks, and disconnected systems. We connect the accounting and ERP systems that vendors and buyers already use, bringing automation to payments, credit, and reconciliation workflows that have operated the same way for decades.

We are a small, fast-moving team solving hard problems at the intersection of fintech, accounting, and enterprise software. If you like working on things that matter, with people who care about getting it right, this is the place.

The Problem

Wholesale distribution relies on complex financial relationships between vendors and buyers. These businesses run on ERP systems like NetSuite, QuickBooks, and Sage — but the processes connecting those systems to payments, credit decisions, and collections are still largely manual. Wholesail is changing that by automating the financial workflows that sit between these systems, making it faster and easier for businesses to get paid and manage risk.

About the Role

We are growing quickly and looking for someone who can help shape the future of our customer success function. This is not a traditional CSM role where you follow a playbook and track renewal dates. This is a role for someone who wants to go deep on a complex product, work with sophisticated customers, and drive real business outcomes. We have extremely low churn (less than 1%) and our customers deeply value their Wholesail partnerships - see testimonials here.

Your accounts will rely on complex accounting systems and operational workflows. You will need to understand how those systems work, how our product fits into them, and how to help customers get more value over time. You will also be one of our strongest feedback channels back to the product team.

We are looking for someone who is naturally curious about AI and automation and thinks about how to use new tools to work smarter. Whether it is streamlining internal processes, finding patterns across accounts