Resource Library

The Secret to Turbocharging Growth? Maximizing the Loss Adjuster Experience

Streamline Tax Compliance for Claims Adjusters: Simplify Your 1099 Process This Season

Our Predictions on the Gig Economy, Tax Policy, and More in 2025

How Telehealth Providers Can Simplify Tax Season—Simplify 1099 Filing with Automation to Save Hours and Eliminate Errors

A fast-growing telehealth enterprise needed a better way to manage the processes behind creating and delivering thousands of 1099 forms to its growing network of mental health providers around the country. They partnered with Wingspan to make it happen.

How to Digitally Transform Your Contractor Payment Process

How These Contractor-Built Businesses Onboarded Their Customers in Record Time

Webinar Recap: 3 Key Challenges with 1099 Filing (and How to Solve Them)

Why Outsourcing Isn’t the Answer for 1099 Filing

The Secret to a Smooth Tax Season? Your Onboarding Process

What Accounting Teams Need to Know About 1099 Filing Penalties

Avoid Penalties and Protect Contractor Relationships with a Streamlined 1099 Filing Process

Why Vendor Payment Systems Fall Short for Contractor Management—and How to Fix It

A Contractor’s Perspective on Getting Paid

Why Traditional Payment Processors Don’t Work for Contractor Management

Empowering the Future of Work: Why I Joined Wingspan to Revolutionize Contractor Payroll and Management

Streamline Your 1099 Filing: How to Tackle Tax Season Stress-Free for Your Contractors and Business

The Challenge of Contractor Payments: Transforming Invoicing into Payroll Efficiency

Finance and accounting experts talk 1099 onboarding best practices, red flags and more in this ultimate masterclass.

Powering the historic growth in telehealth adoption is a rise in independent providers that can directly connect with patients through digital health platforms.

There are a plethora of laws and guidelines you can use to determine whether you're properly classifying your workers.

It's easy to see why businesses are eager to work with independent contractors, but the consequences of misclassifying them can get expensive, fast.

This guide provides in-depth guidance for businesses looking to mitigate their compliance risk when working with contractors at scale.

Not sure whether to classify a worker as an employee or independent contractor? Use this IRS framework to help assess your misclassification risk.

CRU Group COO Bret Peiffer joined our Co-Founder & CTO Greg Franczyk to discuss how the innovative claims company transformed its business using Wingspan.

Delivering a seamless adjuster experience becomes a strategic imperative for claims companies seeking to retain and grow a 1099 workforce.

It’s time to offload your 1099 processing to Wingspan and let it own compliance on your behalf. Here's how easy it is.

It’s time to offload your 1099 processing to Wingspan and let it own compliance on your behalf. Here's how easy it is.

I learned firsthand how stressful and complicated the 1099 filing process is when I became a freelancer at the end of 2016.

I wanted to take a quick moment and reflect back on 2023 at Wingspan, an unforgettable year of momentum, milestones and growth.

1099 filing season can be incredibly stressful for finance teams. Here's everything you need to know before the filing deadline

Get the inside scoop for new 1099 requirements and how world-class finance teams are using automation to simplify and expedite the 1099 filing season.

Get the inside scoop for new 1099 requirements and learn how world-class finance teams are using automation to simplify and expedite the 1099 filing season.

See how businesses use Wingspan to automate onboarding, invoicing, payments, compliance, and benefits for their clients and flexible workforce.

Fintechs that serve the gig economy are forced to contend with a fractured and diverse landscape. Relevant stakeholders range from gig worker-hiring firms, to HR professionals, to gig workers themselves; building out useful and scalable products requires playing 3D chess, keeping key user cases—as well as shifting regulations—top of mind

Between 2016 and 2018, Instacart didn’t pay its Washington, DC contractors tips from customers. These missed tip payments led to a $1.5 million penalty from the Attorney General’s office.

In his Forbes debut, our CEO Anthony Mironov makes the case for a paradigm shift in how companies engage with contractors at scale.

Commercial litigation attorneys John Thompson and J.R. Skrabanek specialize in helping freelancers, entrepreneurs, and startups collect on unpaid invoices.

It will accelerate your cash flow.

He describes his career as a “side hustle on steroids.”

You'll need to pay self-employment taxes if you earn $400 or more.

Sidestep these common pitfalls.

The makeup artist has worked with Marc Jacobs, Parade, Susan Alexandra, Milk Makeup, Refinery29, Man Repeller and more.

With the right approach, you'll save a lot of money—and spare yourself from added stress.

The architect turned ceramicist is the founder of Not Work Related, a Brooklyn-based housewares company.

The branding and marketing consultant shares her go-to inspiration, the best advice she’s ever gotten, and the one thing all freelancers must master.

The photographer, videographer, and composer produced the award-winning documentary “Big Charity."

The brand strategist and copywriter shares the the best advice she’s ever gotten, plus the mindset freelancers must have to succeed.

Find out when you should pay, how much you should save, and what you should do if you can't afford to pay your tax bill.

We're here to celebrate your ingenuity as a solopreneur.

Advice from experts that help small business owners navigate (and overcome) seven thought patterns that can undermine our work.

He hired his former co-workers after he lost his job.

Bonus: Your health and your productivity will soar.

The groundbreaking piece of legislation protects freelancers.

First, get to know some basic vocabulary.

A career coach shares her best tips.

Five foolproof ways to sell your services to a prospective client.

These groups provide advice, collaboration, and even a source of new jobs.

Yes, it's possible.

You'll become more prolific and efficient.

Because discussing pay, workflow and other topics can be really awkward.

It helps you stay legally compliant and protected. It also provides benefits to your customers and employees.

Follow these 7 simple steps.

Here are 8 lawyer-approved ways to recoup your late payments.

Here’s what you need to know about the low interest loan from the government.

Doing your own independent contractor taxes can be overwhelming. But it doesn’t have to be that way.

It's totally doable.

We asked some of the most talented creatives how they keep their schedules busy.

Here are three general pricing models pros use.

Everything you need to know about pandemic-related aid.

It's the difference between a well-oiled business—and utter chaos.

Find out the questions to ask and steps to take.

Try these to streamline your operations, learn new skills, and spark creativity.

Whether through photography, graphic design, or career coaching, Diana Davis wants to help her clients tell their story.

These 10 step will se you up for success.

Many freelancers derive substantial benefits from forming a single-member LLC. But there are pros and cons to consider in making this decision. This article explains a) what an LLC is and why you may want one for your freelance business, and b) what factors you should consider when deciding whether to set up an LLC.

Here's how to figure out if you qualify.

Spoiler: Most of the time, it's not worth claiming.

Read this before you hop on to a site like Upwork or Fiverr.

Try these lawyer-backed tips to help you deal with delayed payments.

"People always react when they know you have their best interests at heart.”

Wingspan supports and stands with the Black Lives Matter movement, condemns police brutality, and believes that police across America must stop murdering Black people with impunity.

Here are five telltale signs shared by Wingspan contributors.

Establish a pre-work routine that’ll help you stay focused and calm.

Follow these freelancer-approved moves to safeguard your time.

Recessions aren’t *necessarily* bad for freelancers.

You *always* need a contract.

Improved Visibility, Fewer Errors, Happier Providers—How Teladoc Transformed Contractor Payments with Wingspan

A fast-growing telehealth enterprise partnered with Wingspan to automate 1099 management, resulting in an 80% reduction in support tickets and over 150 hours saved.

How Mento simplified the onboarding and payment process for their coaches, delivering a seamless experience, streamlining processes, and collecting better data.

The financial wellness platform was looking for a better way to support its army of 1099 insurance agents while building a scalable back office that could keep pace with its rapid growth.

The family-owned loss control inspection company recognized an opportunity to use automation to fundamentally rethink the core, and painstakingly manual, processes used to manage its independent inspectors and run its business.

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.

The fast-growing claims company was looking for ways to transform its adjuster experience into a sustainable competitive advantage.

The story of how a content marketing entrepreneur used Wingspan, and a Zapier integration, to scale his business to new heights.

The high-flying social network darling turned to Wingspan to help scale its 1099 network to 200+ campuses.

The growing insurance company was looking to differentiate itself and drive retention and growth of its 1099 adjuster network.