Wingspan vs. Keeper Tax

If you're here to understand the difference between Wingspan and Keeper Tax, you're in the right place.

Why do Wingspan members switch from Keeper Tax?

All-in-one platform built for the business of one

Wingspan is an an all-in-one platform for freelancers to manage their business. Keeper Tax is a great product if you only need help identifying business deductible transactions from 1099 income.

Like Keeper Tax, Wingspan can link your bank account or credit card and automatically identify tax deductible business expenses.

If you send your own invoices, track income and deductible expenses, set aside for taxes and access to big-company benefits and more into one platform, Wingspan could be a better fit for you.

Track income

Like Keeper Tax, Wingspan helps you identify business expenses that can reduce your tax bill. We'll notify you when you have new transactions to review, and provide you or your CPA an export of all of those transactions to make tax filing a breeze.

Wingspan also tracks your income, which has a big impact on your tax rate. With Wingspan, you can see your income and expenses over time to keep tabs on how much you're earning. Avoid the hassle of adding up your income at tax time by tracking both your income and expenses in one place.

Track other tax deductible expenses that aren't related to your business

Retirement contributions, healthcare costs and donations to charities are all tax-deductible expenses. Wingspan also helps you identify these expenses so you (not Uncle Sam) can keep more of the income you're owed.

A dedicated Member Advocate

Every Wingspan member is assigned a Member Advocate who is dedicated to helping your business be successful. Schedule a call or chat with us at any time. With Wingspan's Tax Hotline, a licensed CPA can answer any tax question you have. The best part: no waiting on hold.

Automated quarterly estimated taxes

When you sign up for Wingspan, you have access to a free FDIC-ensured tax savings account. When you get paid, we'll automatically set aside for taxes. If you're self employed, you're required to pay the IRS quarterly estimated tax payments. With Wingspan, you can pay your taxes directly from our app. And we'll remind you, so you'll never miss a deadline.

Big-company benefits with every membership

Wingspan includes a suite of benefits with every membership including:

  1. $0 Teladoc visits 24/7
  2. A free tax online to get immediate answers from licensed CPAs
  3. A dedicated Health Advocate

These benefits are included in your membership for no additional fee.

Book a demo
Schedule a 30-minute product demo with expert Q&A.
Thanks for your submission. Please book your demo using our Calendly schedule
Trusted by businesses that run on contingent work.

Wingspan vs. Keeper Tax

All-in-one platform
Track business expenses
Automatic tax withholding account
Quarterly estimated tax payments
File simple federal tax returns
Identify personal tax deductions
Track income
Accept payments with custom invoices
Big-company benefits, included
Dedicated member advocate
Keeper Tax
All-in-one platform
Track business expenses
Automatic tax withholding account
Quarterly estimated tax payments
File simple federal tax returns
Identify personal tax deductions
Track income
Accept payments with custom invoices
Big-company benefits, included
Dedicated member advocate
Wingspan
All-in-one platform
Track business expenses
Automatic tax withholding account
Quarterly estimated tax payments
File simple federal tax returns
Identify personal tax deductions
Track income
Accept payments with custom invoices
Big-company benefits, included
Dedicated member advocate

Wingspan is the only platform that handles all the unique processes of contingent work at scale.

Onboarding

Streamline and control onboarding and eligibility.

Stop wasting time chasing W-9s and give your workers an easy way to get verified.

Painless, comprehensive contractor onboarding
Self-service contractor portal that frees up your time
Robust policy management for multiple contractor groups

Payments

Automate invoicing and payments from AR to AP.

Save time making payments, ensure accurate payments, and enhance contractor satisfaction.

Auto-tabulate contractor pay and automate payments
Handle multiple payment rules and schedules
Fast, flexible payment options

Compliance

Offload 1099 creation, filing, and delivery.

Reclaim your January with Wingspan managing your entire 1099-NEC process.

Convenient contractor help desk for questions and corrections
Automatically generate 1099-NEC forms
Secure, compliant filing and delivery

Worker Benefits

Provide access to big company benefits.

Offer the perks of full-time employment, without adding classification risk. Keep workers engaged and satisfied.

Free business checking accounts and debit cards for all workers
Licensed broker, curated insurance options
Financial tools to run their business

An all-in-one flexible work platform 
that delivers real results.

Streamline your operations
$25,000

saved offloading busy season work and automating your critical workflows.

Attract and retain talent
20%

reduced churn by paying your workers faster and more conveniently.

Ensure compliance
$50,000

avoided for each compliance breach related to misclassification.

Looking for an alternative to Keeper Tax?

If you're here to understand the difference between Wingspan and Keeper Tax, you're in the right place.

Why do Wingspan members switch from Keeper Tax?

All-in-one platform built for the business of one

Wingspan is an an all-in-one platform for freelancers to manage their business. Keeper Tax is a great product if you only need help identifying business deductible transactions from 1099 income.

Like Keeper Tax, Wingspan can link your bank account or credit card and automatically identify tax deductible business expenses.

If you send your own invoices, track income and deductible expenses, set aside for taxes and access to big-company benefits and more into one platform, Wingspan could be a better fit for you.

Track income

Like Keeper Tax, Wingspan helps you identify business expenses that can reduce your tax bill. We'll notify you when you have new transactions to review, and provide you or your CPA an export of all of those transactions to make tax filing a breeze.

Wingspan also tracks your income, which has a big impact on your tax rate. With Wingspan, you can see your income and expenses over time to keep tabs on how much you're earning. Avoid the hassle of adding up your income at tax time by tracking both your income and expenses in one place.

Track other tax deductible expenses that aren't related to your business

Retirement contributions, healthcare costs and donations to charities are all tax-deductible expenses. Wingspan also helps you identify these expenses so you (not Uncle Sam) can keep more of the income you're owed.

A dedicated Member Advocate

Every Wingspan member is assigned a Member Advocate who is dedicated to helping your business be successful. Schedule a call or chat with us at any time. With Wingspan's Tax Hotline, a licensed CPA can answer any tax question you have. The best part: no waiting on hold.

Automated quarterly estimated taxes

When you sign up for Wingspan, you have access to a free FDIC-ensured tax savings account. When you get paid, we'll automatically set aside for taxes. If you're self employed, you're required to pay the IRS quarterly estimated tax payments. With Wingspan, you can pay your taxes directly from our app. And we'll remind you, so you'll never miss a deadline.

Big-company benefits with every membership

Wingspan includes a suite of benefits with every membership including:

  1. $0 Teladoc visits 24/7
  2. A free tax online to get immediate answers from licensed CPAs
  3. A dedicated Health Advocate

These benefits are included in your membership for no additional fee.

Keeper Tax
Wingspan
All-in-one platform
Limited
$
Track business expenses
Limited
$
Automatic tax withholding account
Limited
$
Quarterly estimated tax payments
Limited
$
File simple federal tax returns
Limited
$
Identify personal tax deductions
Limited
$
Track income
Limited
$
Accept payments with custom invoices
Limited
$
Big-company benefits, included
Limited
$
Dedicated member advocate
Limited
$
we'll get you going
Getting started
3/9
Sarah
Your member advocate
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Schedule a call with Sarah
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Set yourself up for success. And your business too.

Get personalized help setting up your business and your brand.  Not sure if an LLC is the right move, or wondering how  much to charge clients? We’ve got your back.
Explore registration
get paid

Get paid your way, on your time.

Send invoices effortlessly with tools that make it easier for clients to pay up (and harder for them not to).
Explore payments
scheduled for autopay
Apr 7, 2021
Invoice 1 of 4
$2,409.08
deductible
deductible
personal
deductible
get organized

Bookkeeping you can bank on.

Hold onto more of your hard earned money. Wingspan automatically handles bookkeeping, expenses, and even finds tax deductions for you.
Explore bookkeeping
get covered

Big company benefits for you and yours.

Get the coverage you need and the perks you want with custom insurance and benefits packages.
Explore benefits
Your Benefits
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dental
others
community reviews
I love having the choice to choose the projects I work on and the freedom to create my own work schedule.
Abby Carlson
Graphic Designer
I feel that I can really control my income now that I don’t have to worry about fees being take from my invoices.
Raydene Hansen
Creative Director + Designer
Wingspan vs. Keeper Tax

If you're here to understand the difference between Wingspan and Keeper Tax, you're in the right place.

Why do Wingspan members switch from Keeper Tax?

All-in-one platform built for the business of one

Wingspan is an an all-in-one platform for freelancers to manage their business. Keeper Tax is a great product if you only need help identifying business deductible transactions from 1099 income.

Like Keeper Tax, Wingspan can link your bank account or credit card and automatically identify tax deductible business expenses.

If you send your own invoices, track income and deductible expenses, set aside for taxes and access to big-company benefits and more into one platform, Wingspan could be a better fit for you.

Track income

Like Keeper Tax, Wingspan helps you identify business expenses that can reduce your tax bill. We'll notify you when you have new transactions to review, and provide you or your CPA an export of all of those transactions to make tax filing a breeze.

Wingspan also tracks your income, which has a big impact on your tax rate. With Wingspan, you can see your income and expenses over time to keep tabs on how much you're earning. Avoid the hassle of adding up your income at tax time by tracking both your income and expenses in one place.

Track other tax deductible expenses that aren't related to your business

Retirement contributions, healthcare costs and donations to charities are all tax-deductible expenses. Wingspan also helps you identify these expenses so you (not Uncle Sam) can keep more of the income you're owed.

A dedicated Member Advocate

Every Wingspan member is assigned a Member Advocate who is dedicated to helping your business be successful. Schedule a call or chat with us at any time. With Wingspan's Tax Hotline, a licensed CPA can answer any tax question you have. The best part: no waiting on hold.

Automated quarterly estimated taxes

When you sign up for Wingspan, you have access to a free FDIC-ensured tax savings account. When you get paid, we'll automatically set aside for taxes. If you're self employed, you're required to pay the IRS quarterly estimated tax payments. With Wingspan, you can pay your taxes directly from our app. And we'll remind you, so you'll never miss a deadline.

Big-company benefits with every membership

Wingspan includes a suite of benefits with every membership including:

  1. $0 Teladoc visits 24/7
  2. A free tax online to get immediate answers from licensed CPAs
  3. A dedicated Health Advocate

These benefits are included in your membership for no additional fee.

Book a demo
Schedule a 30-minute product demo with expert Q&A.
Thanks for your submission. Please book your demo using our Calendly schedule
Trusted by businesses that run on contingent work.

Stripe Connect was not designed for B2B flexible work

Not built for contingent staff use cases
  • Payment freezes due to unnecessary KYC requirements
  • No self serve portal
  • No contractor features like benefits and help desk
  • No mapping of your org structure or entities
  • Missing lifecycle capabilities (e.g. background checks, automated calculation of pay, wage garnishment, 1099 dispute resolution)
Designed for developers, not finance teams
  • Developer required for customization
  • Must build TIN verification with separate API 
  • Disconnected 1099 workflow
  • No personalized support
Hidden costs that add up
  • 1-7 business day delay in funding your account requiring extra cash deposits in Stripe
  • >0.25% fee on all payment volume
  • 1.0% processing fee for instant payments
  • Up to $5 per ACH payment
  • Double currency conversions in Canada, Europe and UK

The cost of Stripe can get out of control as you scale

Stripe pricing levers accelerate your costs
  • % of payouts volume
  • $ per active account per month
  • Incremental fees (e.g., tax filings)
Wingspan scales linearly or better with volume
  • Flat $ per provider paid per month (unlimited payments per month)
  • Volume discounts

Wingspan vs. Keeper Tax

Stripe Connect
Wingspan
Streamline and control onboarding and eligibility
Background checks
Background checks
None
Background checks
Built-in
W9 collection and TIN verification
W9 collection and TIN verification
Separate W9 collection and TIN verification API
W9 collection and TIN verification
Built-in and real-time
Policies by entity
Policies by entity
None
Policies by entity
Sophisticated - configured during setup
Automate invoicing and payments from AR to AP
Payment cost
Payment cost
Many transactional fees that scale unpredictably
Payment cost
One fee that scales predictably with your business
Time to fund your account
Time to fund your account
1-7 business days to fund your account
Time to fund your account
2 business days max to fund your account
Payment volume fees
Payment volume fees
>0.25% fee on all payment volume
Payment volume fees
Zero
Payment transaction fees
Payment transaction fees
Up to $5 per ACH payment and 1% fee for instant payments
Payment transaction fees
Zero for ACH and instant payments to Wingspan Wallet
Currency conversions
Currency conversions
All foreign currency transactions must go through a Stripe USD account and incur fees
Currency conversions
Direct payment via local rails in US, Canada, EU and UK with no currency conversion fees
Offload 1099 creation, filing and delivery
1099 filing workflow
1099 filing workflow
Disconnected
1099 filing workflow
Seamless and automated
1099 dispute resolution
1099 dispute resolution
None
1099 dispute resolution
Built-in
Contractor help desk
Contractor help desk
None
Contractor help desk
Included - fully offload Tier 1 support for tax season
Health and financial contractor benefits
Health and financial contractor benefits
None
Health and financial contractor benefits
Free accounting software
Discounted insurance plans
Dozens of additional benefits available

“The contractor help desk and support is where Wingspan really outshined Stripe.”

Keith Diamond
Managing Partner, Pourtastic Tastings
Read case study