Pourtastic switches to Wingspan to upgrade 1099 payment process and save hundreds of hours with automation

The promotional tasting company was looking for a more reliable way to pay its all-important 1099 brand ambassadors and streamline its manually-intensive back office.
Use cases
Contractor Lifecycle
Rapid Payments
Contractor Benefits
Tax Compliance
Fort Worth, TX
No. of Workers
hours saved monthly on admin tasks
hours saved monthly on contractor support
hours saved on 1099 filing
increase in contractor satisfaction
Contractor support is where Wingspan really outshined Stripe.
Keith Diamond
Managing Partner
  • Manual, convoluted and error-prone 1099 payments
  • Spent hours fielding contractor questions & providing support
  • Sub-par contractor support; standalone 1099 filing

  • Fully automated onboarding, payments and approvals
  • Contractor help desk saves hours on support requests
  • Reliable, enterprise-grade 1099 payments engine


Keith Diamond, co-owner and managing partner of Pourtastic Tastings, knew he needed a more reliable way to pay his 1099 contractors. “Getting payments out to our contractors is obviously critical to what we do,” he says. “If they don’t get paid, we’re done. If they don’t get paid on time, we’re in a lot of trouble.” 

His Texas-based hospitality company, which specializes in running promotional tasting events for breweries, wineries and beverage manufacturers, relies on a network of more than 750 brand ambassadors across a handful of states to serve as extensions of their customers’ sales and marketing teams. 

Diamond was growing increasingly frustrated with the company’s 1099 payment processes, particularly given the importance of its contractors to the company’s bottom-line. The company struggled with various payment solutions, from PayPal and Stripe all the way to a platform specifically designed for contractor payments. 

“Stripe worked, but it was super convoluted,” said Diamond.

“The monetary flows were needlessly complicated, it didn’t provide visibility to our contractors on payment status and their support was a nightmare.” 

The contractor payments platform they tried next turned out to be more of a “one-trick pony.” In addition to being error-prone and having insufficient integration features, the company attempted to charge Diamond’s contractors additional fees for filing 1099 forms that would’ve ultimately been passed onto the company. “That was a dealbreaker, as it would’ve essentially doubled what we were paying,” recalls Diamond.


In search of a more purpose-built payment solution that could integrate and scale with his business, Diamond started searching online. Before long, he stumbled upon Wingspan and was immediately intrigued. 

He found Wingspan attractive due to its robust payments engine, API first design, and contractor-centric features. “With 750 contractors, I need the automation to work and be scalable,” says Diamond. While it was slightly more expensive than the previous platform they were using, Diamond recognized the value in being able to offer his contractors a platform purpose-built for 1099 work. 

“The value prop to our contractors all of a sudden became a lot more compelling,” says Diamond.

Wingspan offered a self-service portal for contractors that allowed them to access payment details, withhold taxes, track their income, and access insurance; addressing Pourtastic's need for giving its contractors the tools and visibility needed to do their best work. 

“Our eyes kept getting bigger and bigger as we dove into all of Wingspan’s features,” says Diamond. Not only was the company able to offer its ambassadors access to instant payments, Wingspan’s self-service portal meant it could stem the endless requests coming from contractors asking about payment status, tax information and more. 

“This is where Wingspan really outshined Stripe,” says Diamond.

“With Wingspan, if a contractor has an issue, it’s dealt with responsively. With Stripe, it was essentially a black box and honestly made us look bad.”


Allison Bernhart, Pourtastic’s Director of Information Resources, has been one of the biggest beneficiaries of the company’s back office transformation.

“Wingspan has saved me hundreds of hours processing invoices, running reports and responding to ambassadors,” she says. “It’s an absolute must-have for businesses that run on contractors.” 

She’s seen a considerable increase in efficiency across a number of the company’s operational processes, allowing the company to recoup hundreds of hours annually that they’ve been able to reinvest into growing the business: 

  • 30+ hours saved monthly by automating manual onboarding, payment and approval processes 
  • 20+ hours saved monthly by using Wingspan’s self-service portal to address contractor support issues and questions
  • 30+ hours saved during tax season by offloading 1099 filing and eliminating the need to manually track and retrieve 1099 forms 
  • 35% increase in contractor satisfaction as a result of the intuitive self-service portal and access to benefits 

The fact that 1099 processing and filing was included as part of their Wingspan engagement was particularly notable, considering their previous vendor charged them separately for the service. “1099’s being included were huge,” recalls Bernhart. “We can hand off the entire 1099 process to Wingspan and rest easy knowing it’s taken care of.” 

Recognizing the importance of their ambassadors – the lifeblood of their business – Diamond and Bernhart have been especially pleased with the reaction from its workforce. One Pourtastic contractor, Ionela Doni, recently sent them feedback: “Wingspan is a far superior platform and sets a new standard for independent contractors like me.” 

Not only have they found a novel way to elevate their contractor experience, Bernhardt and Diamond are grateful to have found a reliable partner who understands their business and can scale with them. “Wingspan is the perfect partner to help us scale our business,” exclaims Diamond.

“Wingspan helps us manage payment reliability, back office support and compliance so we can focus on growing the business.”