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, or helping customers think about their own automation journey — we want someone who brings that lens to everything they do.

If you enjoy working on complex products, thinking in systems, and driving real business outcomes, this role will give you the ownership and challenge to do your best work.

In this role, you will:

Operate as the CEO of your own book of accounts to drive financial results for your customers and for Wholesail
Partner closely with Sales, Product and Onboarding teams to advise on customer priorities and drive long-term value
Operate in an intellectually rigorous environment where new ideas and contributions are encouraged
Leverage AI and cutting edge technologies
Handle a complex book of accounts that integrate with various ERPs like Quickbooks, NetSuite, Entree and other vertical/broadline ERPs
Lead executive-level conversations with Controllers, CFOs and operators
Uncover root operational and accounting challenges through deep discovery
Handle escalations independently with a clear point of view
Identify churn risk early and create structured mitigation plans

What excites us:

3-5+ years in SaaS in a technically complex environment
Background as a:

Customer Success Manager/Account Manager handling high-value customers
Customer Success or Solutions Engineer

Strong business acumen; comfortable with Controllers, CFOs, CEOs, & Operators
Clear, structured communication (written and verbal)
Comfort discussing technical subjects internally & externally
History of increasing responsibility or fast growth
Bonus: Experience with ERPs, Product Integrations, Accounting Concepts

Benefits

Work with experienced tech startup founders and a customer-centric team
Competitive compensation
Meaningful Equity - Participate in the upside of building a successful company
Medical, dental, vision, short-term disability insurance and 401K.
$100 per month phone stipend
$50 reimbursable monthly expense for work-from-home internet.
$500 reimbursable towards a work-from-home office setup.