About Wholesail (www.paywholesail.com)
About WholesailWholesail (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 ProblemWholesale 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 RoleWe 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
- 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.
Skills Required
- 3-5+ years in SaaS in a technically complex environment
- Experience as a Customer Success Manager or Account Manager handling high-value customers
- Strong business acumen; comfortable with Controllers, CFOs, CEOs, & Operators
- Clear, structured communication
- Experience with ERPs, Product Integrations, Accounting Concepts
What We Do
Wholesail is a technology startup that builds software to connect wholesalers and their buyers. The company’s first product is an automated invoicing, payment and communication platform that integrates with the accounting systems of wholesale sellers to allow them to get paid faster and decrease losses. For buyers, Wholesail automates the accounts payable process to save them time and money. Wholesail’s initial industry focus is on building a network effect driven payment business in the highly fragmented $1+ trillion US food and beverage distribution market, in which invoicing and payment is nearly entirely manual and paper-driven today. Wholesail was founded by a team of serial entrepreneurs, product managers, engineers and designers who have worked together for nearly a decade. The company is well funded with backing from several venture capital firms and angel investors including early executives and team members from Stripe, Square, Dropbox, Yelp, OpenTable and Everlane. We are looking for highly motivated people to join us on our mission to modernize wholesale trade. If you are passionate about the craft of software engineering or building customer relationships, drop us a line.
