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Technical Onboarding and Support Specialist - Wholesail

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Job Title
Technical Onboarding and Support Specialist
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Job Description

About Wholesail

Wholesail is a 25 person startup that builds software to connect wholesalers and their buyers by automating and digitizing invoicing and payment in the $5 trillion wholesale trade industry, with an initial focus on the food & beverage industry. The company’s first product is an electronic invoicing and payment portal for wholesale sellers, which allows them to get paid faster and decrease losses. For buyers, Wholesail automates the accounts payable & expense management process to save them time and money. 

Wholesail was founded by a team of successful serial entrepreneurs whose prior startups were acquired by OpenTable and who worked together there as product managers, engineers and designers. The company is well funded with backing from a half dozen venture capital firms and 20+ angel investors with backgrounds in FinTech, Payments, SMB Marketplaces, food distribution and restaurants; including early executives and team members from Stripe, Square, Dropbox, PayPal, Yelp, OpenTable and Everlane.

About the Role

As a Wholesail Technical Onboarding and Support Specialist you will wear many hats and play a pivotal role in helping onboarding & supporting our customers. You’ll have a direct impact on the customer experience by helping us shape our technical post-sale strategies. 

You Will:

  • Provide a white-glove onboarding experience for new customers remotely with the potential for some in-person meetings, walking them through the technical steps of the process.
  • Work closely with our sales and account management teams to drive all technical aspects of the post-sales engagement with our customers.
  • Maintain our support operations for our customers by resolving Tier I & Tier II technical issues using clear communication.
  • For customers using on-premise accounting systems (e.g. QuickBooks Desktop), provide technical advice and support to ensure Wholesail syncs consistently and reliably. 
  • Identify and help resolve accounting issues for new customers so they can have a seamless launch with Wholesail.
  • Respond to customer service inquiries regarding payment issues, accounting system sync issues, or other requests.
  • Provide feedback on up and coming development so that Wholesail releases software that works.
  • Partner with our Account Management team to increase user adoption of our product by supporting the technical aspects of customer campaigns.
  • Support the day-to-day maintenance of our business tools including Salesforce, BigQuery, Calendly, Zoom and more.

Required Experience & Skills

  • 1-3 years of experience in a customer success or technical support role.
  • 1-3 years of experience in project management.
  • Curious nature with a desire to learn new skills & master new tools.
  • Passion for providing great customer service and doing what’s right for the customer.
  • Excellent written and verbal communication skills with experience in creating highly detailed and organized documents to support customer success. 
  • Experience with key tools for the job: SQL, spreadsheets (Excel, Google Sheets), Remote desktop applications (VNC, TeamViewer, Microsoft Remote Desktop).
  • Ability to work autonomously and identify solutions to new problems without help from others. 
  • Ability to work collaboratively and know when to escalate an issue and involve other team members to solve a time-sensitive customer issue. 
  • Self-motivated and able to perform well under pressure and against bold goals and deadlines.
  • Strong attention to detail and task management skills, even when moving quickly to respond to an urgent issue. 

Bonus Experience

  • Accounting or bookkeeping experience (or related degree) would be very valuable.
  • Team member of an early stage startup.
  • Experience with accounting software (e.g. QuickBooks Online or Desktop). 
  • Experience with providing technical support for on-prem software. 
  • Passion for or experience with hospitality, restaurants, or food.
  • College degree or certification in a technical field.


  • Work with experienced tech startup founders and a customer centric team.
  • Medical, dental, and vision coverage.
  • Home office budget.
  • Paid vacation and sick leave.

Wholesail Headquarters Location

San Francisco, CA

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Wholesail Company Size

Between 20 - 50 employees

Wholesail Founded Year


Wholesail Total Amount Raised


Wholesail Funding Rounds

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  • Series Unknown

    $22,585,494 USD