Simplify onboarding with eSignatures from your contractors

September 25, 2022

When you hire a new contractor, it's a hassle to deal with the paperwork. With Wingspan, you can now assign eSignature documents to your contractors to sign.

When you invite them to Wingspan, they'll be prompted to review and sign the document. You'll always see an up-to-date record of what is incomplete on their profile.

To enable eSignatures for your company, speak with your Account Manager.


Upgraded receipt & invoice PDFs

September 13, 2022

We've just released useful improvements to the invoice and receipt PDF

  • The design was overhauled
  • Your logo appears on the top right
  • International payment details appear if enabled
  • Payment information is now included on the receipt
  • Your client's address appears on the invoice, if included
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Enterprise Single Sign-On

September 1, 2022

With Wingspan's Single Sign-On, employees can use their organization credentials to log in or access Wingspan from any device or any location, without compromising on security. With this feature, you can easily eliminate the use of simple passwords that present a security risk, while also improving productivity with one-click access to Wingspan.

Currently, Wingspan's Single Sign-On supports all major identity providers — Google Cloud Identity, Okta, Azure, OneLogin and 9+ more. We also offer the flexibility to integrate any other identity management provider of your choice.

To enable SSO, get in touch with your Account Manager.


Wingspan Wallet: business banking with faster payments, automatic write-offs & no fees

May 30, 2022

We're excited to announce Wingspan Wallet – the free bank account and debit card for your business. Save on taxes, manage your finances and get paid faster. All with no hidden fees and no minimums.


How much does it cost?

Wingspan wallet is free, including:

  • $0 ACH transfers
  • $0 to receive domestic wire transfers
  • $0 account minimum
  • $0 monthly cost
  • $0 overdraft fees

Get started

Instant payouts

May 13, 2022

Instant Payouts allow you to send your income to an eligible debit card within 60 minutes, giving you on-demand access to funds. Instant Payouts are available 24x7, including nights, weekends and holidays, for a fee of 1% of the payout amount.

How does it work?

You will see a new request instant payout button in payment confirmation emails & in your pending invoices list in Wingspan. Select an invoice for instant payout and enter your debit card information. Your payment will arrive within 60 minutes.


Have any more questions? Read our FAQ.

Import transactions from a spreadsheet instantly

June 1, 2021

Easily import transactions with Wingspan's new spreadsheet transaction upload tool.

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  • Import transactions instantly from any U.S. bank account.
  • Migrate transactions from another bookkeeping tool like QuickBooks.
  • Pull in income from an invoicing platform like Stripe.

How It Works:

  1. Upload a spreadsheet or CSV that include columns for transaction name, amount and date.
  2. Use our easy uploader tool to clean up your data.
  3. Your transactions are uploaded to Income & Expenses. Easy!

Add receipts to transactions

May 17, 2021

Stay organized by attaching receipts to transactions in Income & Expenses. Simply select a transaction and drag in your receipt to upload it. The receipt is securely saved in Wingspan and is always accessible, even without a membership.

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Self-employed tax calendar

March 23, 2021

Stay on top of self-employed (1099) tax deadlines with Wingspan's new tax calendar.

The calendar includes:

  • Quarterly estimated tax deadlines
  • Tax return filing deadlines
  • When you should expect to receive 1099s from your clients

Add to Google Calendar →

Self employed tax calendar preview

Update multiple transactions at once

March 22, 2021

If you have many similar transactions to update in the same way, use Wingspan's new search and bulk editing features to get it done fast.

  • Delete and rename transactions
  • Modify the transaction amount
  • Mark transactions as business/non-business
  • Change transaction categories (e.g. Food & Drink)
  • Update transaction type (e.g. Income)
Bulk Update Preview

Export tax documents

March 16, 2021

Tax season is coming up. You can now request an export of your 2020 Schedule-C or Tax Summary spreadsheet in Taxes.

How do I use it? You can share this sheet with your accountant to file your taxes, or file yourself with a tool like TurboTax.

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Wingspan's Tax Summary sheet includes:

  • A Schedule-C Tax Summary
  • All of your Income & Expense transactions
  • Profit & Loss statements

What is the Schedule-C?

As a self-employed individual, you need to fill out an IRS Schedule C to report how much money you made in your business. This form must included with your income tax return if you had self-employment (1099) income.

Add a custom note to transactions

March 10, 2021

Capture more information on transactions with new custom notes on any transaction in Income & Expenses.

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For example, add details like client information or additional context for your accountant. When you export your tax-ready financials for your filing, those notes will be included for you or your accountant's reference.

Stay organized with a new transaction list and P&L.

February 23, 2021

You don’t have to be a math whiz to keep your business organized. Wingspan’s new Bookkeeping tool does all the heavy lifting.

What's new:

  • See all your business's transactions at a glance
  • Filter transactions by type, date range, or account
  • Understand your business' Profit & Loss by any custom date range

Check out the new Income & Expenses →


Love Wingspan? Refer a self-employed individual and you'll both get $50 🎁

January 24, 2021

Wingspan now offers a referral program!

Tell other self-employed individuals about Wingspan. You'll both get $50 when they subscribe to a membership.

How it works

  1. Click Refer a Friend
  2. Share your link with other self-employed people
  3. They sign up and subscribe to a membership
  4. You both get $50 via your Pay Link
Wingspan refer & earn

Get paid even faster with Autopay 🪄

January 22, 2021

You've already used our secure platform to send your clients a one-click invoice via text, DM, email, or chat. And we just made that one-click approval go to zero clicks.

Let us know what you're doing with all your new free time and 💰in your bank 🏄‍♀️

We're excited to hear your feedback! 🙏

PDFs of invoices are now automatically attached to emails 📎

January 11, 2021
Thanks for the invoice, can you send a PDF?

Some larger clients have their own systems and processes. With all those rigid systems usually comes a default behavior to ask for a PDF invoice before even looking at the digital invoice.

In an effort to get you paid as quickly as possible, we started attaching PDFs directly to the invoices emailed to your clients. These PDFs are still accessible through each invoice link, but hopefully that attachment upfront saves a few unnecessary emails 😌

We ❤️ your feedback, keep it coming!

Make it easier for your clients to pay you

January 3, 2021

Get paid faster with one-click payments for your clients

We’ve completely redesigned your client experience to make it as easy as possible for your clients to pay you. Send your client an invoice via email, text, chat, or DM. They're no longer prompted to create an account and we made it super clear that Wingspan is a simple and secure payment gateway and that they can pay invoices for free, any way they'd prefer.

Want to test drive your client's payment experience? Check it out here.

Introducing payment links

January 2, 2021

Use your custom link to accept payments directly into your bank account—for free payment link

Spend less time chasing invoices and more time on what matters: your business. Send your client your Wingspan personal pay link. Think of it like Venmo, but way more business-friendly. (And we don't hold your cash and your client doesn’t need an account.) Claim your link before someone grabs your handle!

Here's how it works:

  1. Share your link in a text message, email, or chat.
  2. Your client is taken to a page that lets them send you money, no invoice necessary. They can pay however they like—ACH, wire transfer, credit or debit—for free.
  3. Once your client hits "pay," your money is processed and deposited directly into your bank account.
  4. We don't hold your cash like Venmo or PayPal, and it's free for you and your clients.

More power and customization to streamline your invoicing workflow

January 1, 2021

You asked—and we listened. Now, when you create an invoice, you can also schedule to send future invoices. (Set it and forget it and get back to life.) We’ve also added new fields where you can add your hourly rate calculations, as well as the ability to attach a PDF (for things like timesheets and W-9s).

Introducing Benefits with Wingspan

December 31, 2020

Giving you and your family peace of mind (and cool perks) in 2021.

Wingspan Benefits

Working for yourself is harder than it should be.

Even before the COVID-19 pandemic, self-employed individuals struggled with a host of scary unknowns. At Wingspan, our mission is to take away the burden of administrative tasks—like invoicing, bookkeeping, taxes, and benefits—to empower you to do your best work. We want our members to enjoy the freedom of freelancing by giving them the safety net of a big company.

Our goal is to provide self-employed professionals with essential tools and support to work the way they want.

Today, we're proud to announce Benefits by Wingspan. Say goodbye to confusing insurance jargon and the headache of finding affordable coverage for you and your family. You'll also get instant access to a curated suite of non-insurance benefits that you'd typically only find at Fortune 500 companies. The best part? Most benefits are included with the price of your Wingspan membership and cover your dependents.

What's included?

  • Easier insurance: We'll help you find, enroll in, and get the most out of your health insurance plan. (And even more, coming soon 😉)
  • Talk to a doctor for free with 24/7 access to telemedicine.
  • Save 15% to 50% on dental expenses like cleanings, x-rays, crowns and fillings.
  • Discounts on pet care at participating veterinarians, sitting and walking services, and prescriptions for your furry friends.
  • Up to 30% off alternative medicine services like acupuncture, massage therapy, yoga, and more.
  • Dedicated support from your Health Advocate, who can help you negotiate down your health insurance bill and find affordable care.

Here's how it works

  1. Go to Wingspan Benefits to shop for medical coverage and other benefits.
  2. Activate the benefits you need.
  3. Wingspan can provide 1:1 guidance along the way.

Stay on top of new transactions

December 14, 2020

Review new transactions to stay organized.

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How does it work?

Once you connect your bank account to Wingspan, new transactions will be imported. First, review potential business income to ensure your profit is up-to-date. Then, identify any business expenses to write off.

As new transactions are synced from your bank account, you can review them at any time.

See it in action

Introducing Tax Withholding

November 18, 2020

Taxes. They’re inevitable. But, they don’t have to be a pain in the neck. Wingspan Withholding is an easy way to save for taxes.

How does it work?

Every time you get paid through Wingspan, we will automatically set aside a proportion of the income into a savings account you can always access. When it comes to quarterly tax payments, you can pay the IRS directly from Wingspan.

Just like a full time employee, the income you receive excludes taxes and will be yours to spend!

Get Started →

Getting started with Wingspan

November 11, 2020

Learn the basics of Wingspan in a few minutes minutes with our new demo video:

Send test invoices

October 20, 2020

You can now send yourself test invoices. We're confident your clients will love paying you through Wingspan, now you can be confident too!

  1. Send yourself our default test invoice or one you've customized
  2. It'll land in your email for you to check it out
  3. Click through to test the full client payment experience
  4. Start sending invoices and watch us get you paid

Introducing your File Vault

October 14, 2020

Create professional documents with confidence

For far too long, independent professionals have had to navigate their lives with limited access to the systems and documents they need to succeed. Not anymore. We're leaving a paper trail of some of freelancing's most classified information.

Introducing the File Vault, a first-of-it's-kind digital briefcase featuring editable and downloadable contracts and templates prepared by experts. Wingspan members will be able to compose client-facing proposals, access tax-ready financial forms, and upload & store their own documents, all in one secure place.

Say hello to contracts

October 6, 2020

Here by popular demand: contract templates! Download a completely customizable contract to jumpstart your business and keep yourself protected.

  • Drawn up by lawyers who specialize in freelance clients & small businesses
  • Downloadable and editable to suit your specific needs
  • Still need help? Reach out to your member advocate to schedule a 30-minute consultation

Get paid *on time*

October 1, 2020

Never wait (and wait and wait) for a client to pay you again. Now, you can tell Wingspan to send automatic reminders when your invoice is overdue

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  • Completely customizable: you decide when an invoice is overdue, and if you want to send a reminder
  • No client is the same, so set your preferences for each individual invoice
  • We'll never send a reminder without your explicit permission

Recurring invoices for retainers!

September 25, 2020
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Working longterm with a client?

  • Set up recurring invoices on autopilot
  • Get paid promptly at the same time every week or month

Auto-imports have landed in bookkeeping

September 23, 2020

You didn't get into freelancing to run your own accounting department. Now you can auto-import your transactions into our bookkeeping product!

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  • Automatically track your financials via linked accounts for an always-available, up-to-date personal financial dashboard
  • See a snapshot of you how much income has come in, total expenses incurred and estimates of your tax liability
  • Get the peace of mind you need to focus on your craft

Preview any invoice before you hit send!

September 22, 2020

You asked, we answered. You can now preview any invoice before sending it off your client!

  • Double check your inputs and feel confident you know exactly what's arriving in someone's inbox—all without interrupting your process.
  • Preview your entire invoice email, including to, from, and subject

Wingspan Tax Prep is here!

September 15, 2020

As you run your business, we keep track of your income, expenses, profit, and losses. When it's time to file, you can use Wingspan Tax Prep to export your tax-ready financials— including your Schedule-C—to use for DIY filing or with your CPA.

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A spreadsheet of Schedule C calculations. Transparent calculations that map all of your transactions correctly to every field in the Schedule C form.

Profit and loss breakdown. An overview of your financial standings.

All income and expenses. Edit or add business transactions to this list to automatically recalculate the Schedule C data

Now let's get in [business] formation

September 8, 2020
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It's time to get down to business. Now you can schedule a one-on-one consultation with a Member Advocate to decide if incorporating your business is right for you.

  • Get information and advice on the difference between an LLC vs. an S-Corp
  • Step-by-step walkthrough of all filing paperwork
  • File with the government on your behalf

Personal Pay Link

August 25, 2020

We've made it easier to get paid effortlessly!

Check out our new personal pay link feature –– now available as part of the Wingspan invoicing experience!

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  • Send your own custom URL to clients and make it easier for them to pay you
  • Reduce the number of unbillable hours spent on admin while improving the reliability of the payment
  • Get paid on your terms and pass the payment processing fee to your clients

A whole new dashboard

August 10, 2020

We make it easy to complete tasks, access resources on growing your business, and see how you're tracking this month.

  • See an overview of all your invoices this month and their statuses
  • Easily check on any outstanding to-dos to stay organized
  • Access articles & resources to help you level up

Getting started with freelancing

July 14, 2020
Congratulations you're a freelancer! Now you gotta x, y, z. We've already figured it out for you.

Going into business for yourself can be very exciting: you have the opportunity to work on what you want, when you want, and how you want. However, after making this transition from full time employment to freelancing, many independent contractors quickly find themselves consumed by uncertainty and crippled by administrative overhead. They find themselves asking, why isn’t there a single source of truth that tells me everything that I need to do, helps me get it done, and ensures I stay on top of things?

Today that changes. Wingspan is proud to announce the release of “Getting Started with Freelancing”: a comprehensive, step-by-step guided experience that demystifies all the things you need to know as a freelancer, and helps you stay on top of it all. Once you’ve gone through the getting started experience you’ll be armed with everything you need to be confident, so you can focus on doing the work you love.

wingspan works together

The smartest way to work for yourself.

We think you’ll agree. Try Wingspan free for 14 days, no strings attached.