Enterprise Onboarding Specialist

Enterprise Onboarding Specialist - Remote (US)

About Wholesail (www.paywholesail.com)

Wholesail empowers 400+ wholesalers to confidently manage payment risk without compromising customer relationships or growth. By combining credit onboarding tools, automated AR communications, a payment portal, and accounts receivable workflow tools, Wholesail helps customers get paid 35% faster, streamline AR processes, reduce credit card costs, and enhance the customer experience.

Wholesail was founded by serial entrepreneurs to facilitate enduring relationships between food and beverage wholesalers and their restaurant and grocery buyers. The company is well-funded, with backing from a half dozen venture capital firms and more than 20 angel investors with backgrounds in fintech, payments, SMB marketplaces, and distribution, including early team members from Stripe, Square, Dropbox, Yelp, OpenTable, and Everlane.

About the Role

We are hiring an Enterprise Onboarding Specialist to guide new sellers through their implementation and set them up for long-term success on Wholesail. This role is customer-facing, process-oriented, and increasingly technical as Wholesail expands its integration ecosystem.

You will support sellers using a variety of accounting and ERP systems, including QuickBooks, Xero, NetSuite, FlexiBake, and Entree. You will also help onboard our first sellers on new integrations and provide feedback that shapes how Wholesail scales those workflows. You should be a fast learner who enjoys solving problems, navigating systems, and working with customers.

This is a highly cross-functional role that partners with Sales, Customer Success, Product, Engineering, and Support. You’ll be mentored by a hands-on leader who previously handled Onboarding and led Account Management at OpenTable as well as developed the Onboarding and Customer Success functions at Wholesail.

In this role, you will:

Lead new seller onboarding

• Guide sellers through onboarding milestones and expectations maintaining consistent communication throughout for both existing + new integrations

• Conduct Trainings for AR teams, Sales teams, and administrators

• Ensure all questions are answered and areas of friction smoothed for customers in the onboarding process

• Support high-payment-volume sellers, multi-entity structures, and advanced AR workflows

• Contribute to documentation and processes that allow Wholesail to scale new integrations

Collaborate across departments

• Partner with Sales to make the transition seamless across the sales → implementation process

• Collaborate with the existing Onboarding Specialist to share learnings and balance workload

• Provide Customer Success with a complete, clean handoff at go-live

• Communicate seller insights, trends, and opportunities to Product and Engineering

What excites us:

• 2 to 5 years of experience in onboarding, implementation, sales/solutions engineering.
At least 2 years must be in either implementation and/or sales engineering.

• Excellent verbal and written communication skills

• Comfortable with SQL, JSON, & manipulating data sets in tools like Excel or Google Sheets

• Bonus: Familiar with Python, ERP and/or Accounting Software

• Strong project management and organizational abilities

• Comfortable leading customer-facing calls and managing expectations

• High attention to detail and reliable follow-through

• Experience with integrations, data troubleshooting, or API-based tools

• Prior involvement in process or documentation improvement

Benefits

• Work with experienced tech startup founders and a customer-centric team

• Compensation based on experience $85k-$105k

• Medical, dental, vision, short-term disability insurance and 401K.

• $100 per month phone stipend

• $50 reimbursable monthly expense for work-from-home internet.

• 15 PTO (Paid Time Off) and 5 paid sick days per year, plus paid holidays.

• $500 reimbursable towards a work-from-home office setup.

• Equity