Guides and insights from Wingspan on onboarding, paying, and supporting 1099 contractors and flexible workforces.https://www.wingspan.app/en-ushttps://www.wingspan.app/articles/best-contractor-payroll-services-2026/https://www.wingspan.app/articles/best-contractor-payroll-services-2026/A Guide to Paying Freelancers and Staying Compliant (2026 Edition)Tue, 02 Jun 2026 17:34:00 GMTPaymentshttps://www.wingspan.app/articles/self-service/https://www.wingspan.app/articles/self-service/“When will I get paid?”Tue, 02 Jun 2026 17:29:00 GMTFor Contractorshttps://www.wingspan.app/articles/the-state-of-contractor-management/https://www.wingspan.app/articles/the-state-of-contractor-management/Your contractor workforce is scaling. The systems running it aren't.Wed, 20 May 2026 19:02:00 GMTFuture of Workhttps://www.wingspan.app/articles/building-for-whats-next/https://www.wingspan.app/articles/building-for-whats-next/60% of the companies we surveyed are taking action.Mon, 18 May 2026 14:21:00 GMTFuture of Workhttps://www.wingspan.app/articles/rethinking-the-contractor-relationship/https://www.wingspan.app/articles/rethinking-the-contractor-relationship/It starts with onboarding pain, but it doesn’t end there.Mon, 11 May 2026 17:39:00 GMTFuture of Workhttps://www.wingspan.app/articles/wingspan-product-update-intl-us-persons-support/https://www.wingspan.app/articles/wingspan-product-update-intl-us-persons-support/Not every contractor living abroad should be treated as an international payee.Wed, 06 May 2026 16:59:00 GMTFor Contractorshttps://www.wingspan.app/articles/wingspan-product-update-work-logging/https://www.wingspan.app/articles/wingspan-product-update-work-logging/Managing contractor work hours shouldn't require spreadsheets, separate time-tracking tools, or support tickets.Wed, 06 May 2026 16:53:00 GMTFor Contractorshttps://www.wingspan.app/articles/the-hidden-toll-of-managing-contractors-at-scale/https://www.wingspan.app/articles/the-hidden-toll-of-managing-contractors-at-scale/It’s a serious operational burden.Wed, 06 May 2026 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/contractors-are-the-backbone-of-the-modern-workforce/https://www.wingspan.app/articles/contractors-are-the-backbone-of-the-modern-workforce/For them, it’s more than a gig.Mon, 27 Apr 2026 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/scaling-the-flexible-workforce-beyond-ap-automation-to-revenue-protection/https://www.wingspan.app/articles/scaling-the-flexible-workforce-beyond-ap-automation-to-revenue-protection/Discover how a purpose-built system ensures compliance, speeds up payments, and protects your bottom line.Fri, 24 Apr 2026 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/what-500-hr-and-finance-leaders-revealed-about-managing-contractors/https://www.wingspan.app/articles/what-500-hr-and-finance-leaders-revealed-about-managing-contractors/A contractor management crisis is hiding in plain sight.Thu, 16 Apr 2026 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/q1-2026-wingspan-product-updates/https://www.wingspan.app/articles/q1-2026-wingspan-product-updates/At Wingspan, we’re focused on solving the unique needs of contractors across the entire management lifecycle.Tue, 31 Mar 2026 17:21:00 GMTUpdateshttps://www.wingspan.app/articles/why-location-matters-for-freelancers-working-in-these-states/https://www.wingspan.app/articles/why-location-matters-for-freelancers-working-in-these-states/Some states are not like the others.Wed, 18 Mar 2026 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/best-contractor-payroll-services/https://www.wingspan.app/articles/best-contractor-payroll-services/Why Modern Enterprises are Moving Beyond Manual PayrollFri, 13 Mar 2026 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/what-freelancers-need-to-know-about-state-contracting-laws/https://www.wingspan.app/articles/what-freelancers-need-to-know-about-state-contracting-laws/Let’s learn the basics.Wed, 04 Mar 2026 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/buyers-guide-how-to-evaluate-contractor-management-platforms-in-2026/https://www.wingspan.app/articles/buyers-guide-how-to-evaluate-contractor-management-platforms-in-2026/Move beyond legacy AP tools and discover how modern platforms automate compliance, accelerate onboarding, and unlock the full potential of your contingent workforce.Mon, 02 Mar 2026 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/how-occupational-accident-insurance-oai-can-protect-you/https://www.wingspan.app/articles/how-occupational-accident-insurance-oai-can-protect-you/Expect the unexpected.Wed, 25 Feb 2026 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/the-top-4-contractor-management-trends-shaping-2026/https://www.wingspan.app/articles/the-top-4-contractor-management-trends-shaping-2026/What Economic Upheaval, AI, and Changing Regulations Mean for Your 1099 WorkforceTue, 24 Feb 2026 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/when-are-estimated-taxes-due-in-2026/https://www.wingspan.app/articles/when-are-estimated-taxes-due-in-2026/The next payment is due sooner than you might think.Thu, 05 Feb 2026 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/freelancers-guide-to-ruling-the-world-how-to-find-free-productivity-apps-and-tools-to-supercharge-your-business/https://www.wingspan.app/articles/freelancers-guide-to-ruling-the-world-how-to-find-free-productivity-apps-and-tools-to-supercharge-your-business/Want to streamline your operations, learn new skills, and spark creativity? Start here.Wed, 28 Jan 2026 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/why-contractors-will-be-essential-to-your-company-in-2026/https://www.wingspan.app/articles/why-contractors-will-be-essential-to-your-company-in-2026/These highly skilled professionals are the future of the modern workforce.Wed, 14 Jan 2026 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/why-contract-work-is-perfect-for-this-moment/https://www.wingspan.app/articles/why-contract-work-is-perfect-for-this-moment/Your next side hustle could start today.Wed, 07 Jan 2026 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/wingspan-q4-2025-product-release-roundup/https://www.wingspan.app/articles/wingspan-q4-2025-product-release-roundup/Here’s a look at what’s new at WingspanWed, 31 Dec 2025 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/the-top-trends-of-2025-what-we-predicted-correctly-and-what-didnt-come-true-after-all/https://www.wingspan.app/articles/the-top-trends-of-2025-what-we-predicted-correctly-and-what-didnt-come-true-after-all/4 Experts Predicted These Top Trends for 2025 - How Did They Do? Thu, 18 Dec 2025 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/got-questions-about-your-1099-weve-got-answers/https://www.wingspan.app/articles/got-questions-about-your-1099-weve-got-answers/There are no dumb questions here.Thu, 11 Dec 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/the-1099-checklist-you-need-for-tax-season/https://www.wingspan.app/articles/the-1099-checklist-you-need-for-tax-season/‘Tis the season.Wed, 03 Dec 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/3-experts-on-managing-1099-behavioral-health-networks/https://www.wingspan.app/articles/3-experts-on-managing-1099-behavioral-health-networks/How to Build, Manage, and Maintain ThemThu, 20 Nov 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/this-is-how-to-get-your-small-business-ready-for-2026/https://www.wingspan.app/articles/this-is-how-to-get-your-small-business-ready-for-2026/It’s time to separate your business and personal bank accounts.Wed, 19 Nov 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/confused-about-your-freelance-taxes-start-here/https://www.wingspan.app/articles/confused-about-your-freelance-taxes-start-here/Yeah, it’s tax time already. Again.Mon, 10 Nov 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/how-the-telehealth-contractor-market-has-changed-since-2020/https://www.wingspan.app/articles/how-the-telehealth-contractor-market-has-changed-since-2020/Telehealth Today Looks Very Different—Here’s How That Matters For Your BusinessThu, 06 Nov 2025 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/scale-without-the-year-end-data-consolidation-burden-why-november-matters/https://www.wingspan.app/articles/scale-without-the-year-end-data-consolidation-burden-why-november-matters/How to eliminate weeks of manual reconciliation and ensure seamless January filingWed, 05 Nov 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/what-contractors-need-to-know-about-the-1099-k/https://www.wingspan.app/articles/what-contractors-need-to-know-about-the-1099-k/Heads up: the reporting threshold is changing for 2025 and 2026.Wed, 05 Nov 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/how-new-changes-to-the-1099-nec-will-affect-contractors/https://www.wingspan.app/articles/how-new-changes-to-the-1099-nec-will-affect-contractors/Are you a contractor earning more than $600 per year? This affects you.Wed, 29 Oct 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/managing-the-new-behavioral-health-workforce-1099-compliance-and-care-delivery-at-scale/https://www.wingspan.app/articles/managing-the-new-behavioral-health-workforce-1099-compliance-and-care-delivery-at-scale/The Rise of 1099 Provider Networks in Behavioral Health—and How to Manage ThemWed, 29 Oct 2025 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/the-7-pain-points-that-make-january-1099-season-a-nightmare-and-how-to-eliminate-them-before-tax-season-hits/https://www.wingspan.app/articles/the-7-pain-points-that-make-january-1099-season-a-nightmare-and-how-to-eliminate-them-before-tax-season-hits/Stop scrambling every January: automate the manual work now and walk into tax season completely preparedTue, 28 Oct 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/these-are-the-biggest-1099-nec-filing-challenges-and-how-to-solve-them/https://www.wingspan.app/articles/these-are-the-biggest-1099-nec-filing-challenges-and-how-to-solve-them/Hint: the solution involves automation. Thu, 23 Oct 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/stop-chasing-w-9s-why-smart-companies-automate-contractor-validation-before-tax-season/https://www.wingspan.app/articles/stop-chasing-w-9s-why-smart-companies-automate-contractor-validation-before-tax-season/The hidden costs of manual W-9 collection and last-minute TIN validation errors: and how to eliminate bothThu, 23 Oct 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/wingspan-q3-2025-product-release-roundup/https://www.wingspan.app/articles/wingspan-q3-2025-product-release-roundup/Here’s a look at what’s new at WingspanWed, 15 Oct 2025 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/how-to-build-hr-platforms-for-the-new-workforce-reality/https://www.wingspan.app/articles/how-to-build-hr-platforms-for-the-new-workforce-reality/Webinar Recap - Don’t Make Contractors an AfterthoughtWed, 15 Oct 2025 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/why-liability-insurance-is-worth-buying-for-claims-adjusters/https://www.wingspan.app/articles/why-liability-insurance-is-worth-buying-for-claims-adjusters/It’s always good to have back-up.Wed, 24 Sep 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/why-contractors-should-consider-accident-insurance/https://www.wingspan.app/articles/why-contractors-should-consider-accident-insurance/Reason #1: Occupational Accident Insurance can reimburse lost incomeFri, 19 Sep 2025 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/dont-make-contractors-an-afterthought/https://www.wingspan.app/articles/dont-make-contractors-an-afterthought/How to Build an HR Platform for a Mixed WorkforceThu, 18 Sep 2025 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/wingspan-raises-24m-series-b-to-scale-embedded-contractor-management/https://www.wingspan.app/articles/wingspan-raises-24m-series-b-to-scale-embedded-contractor-management/Series B led by Touring Capital will propel Wingspan’s mission to make flexible work effortlessTue, 29 Jul 2025 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/insperity-partners-with-wingspan-to-launch-first-embedded-contractor-management-solution/https://www.wingspan.app/articles/insperity-partners-with-wingspan-to-launch-first-embedded-contractor-management-solution/Enabling Seamless Onboarding and Payments for Thousands of 1099 WorkersTue, 22 Jul 2025 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/introducing-wingspan-embed-power-contractor-management-directly-within-your-platform/https://www.wingspan.app/articles/introducing-wingspan-embed-power-contractor-management-directly-within-your-platform/Legacy HR Systems Weren’t Built for the Modern WorkforceMon, 21 Jul 2025 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/q2-product-release-recap/https://www.wingspan.app/articles/q2-product-release-recap/From ID Verification to Approval Workflows: Here’s What We Shipped in Q2Thu, 17 Jul 2025 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/how-3-businesses-completely-transformed-their-payroll-process/https://www.wingspan.app/articles/how-3-businesses-completely-transformed-their-payroll-process/3 Payroll Experts on Streamlining Their Payout ProcessWed, 14 May 2025 00:00:00 GMTCustomer Storieshttps://www.wingspan.app/articles/how-to-onboard-contractors-twice-as-fast/https://www.wingspan.app/articles/how-to-onboard-contractors-twice-as-fast/3 Experts on How to Onboard Your Contractors FasterWed, 14 May 2025 00:00:00 GMTCustomer Storieshttps://www.wingspan.app/articles/wingspan-vs-unit-banking-built-for-contractors/https://www.wingspan.app/articles/wingspan-vs-unit-banking-built-for-contractors/Why You Should Partner with Wingspan for a Better Banking ExperienceThu, 08 May 2025 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/wingspan-vs-stripe-how-to-build-a-better-payments-process/https://www.wingspan.app/articles/wingspan-vs-stripe-how-to-build-a-better-payments-process/Why You Should Partner with Wingspan for a Better Payments ProcessWed, 30 Apr 2025 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/you-need-more-than-just-payroll-to-manage-your-contractors/https://www.wingspan.app/articles/you-need-more-than-just-payroll-to-manage-your-contractors/Why you need a comprehensive contractor management platformTue, 15 Apr 2025 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/how-easy-it-is-to-build-with-wingspan/https://www.wingspan.app/articles/how-easy-it-is-to-build-with-wingspan/Add 1099 Capabilities to Your Software with WingspanTue, 08 Apr 2025 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/what-claims-companies-need-to-know-about-tax-season/https://www.wingspan.app/articles/what-claims-companies-need-to-know-about-tax-season/Streamline Tax Compliance for Claims Adjusters: Simplify Your 1099 Process This SeasonThu, 16 Jan 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/onboard-your-contractors-in-weeks-not-months-with-wingspan/https://www.wingspan.app/articles/onboard-your-contractors-in-weeks-not-months-with-wingspan/How These Contractor-Built Businesses Onboarded Their Customers in Record TimeThu, 09 Jan 2025 00:00:00 GMTOnboardinghttps://www.wingspan.app/articles/digital-transformation-in-finance-wingspans-role-in-reshaping-contractor-payments/https://www.wingspan.app/articles/digital-transformation-in-finance-wingspans-role-in-reshaping-contractor-payments/How to Digitally Transform Your Contractor Payment ProcessTue, 07 Jan 2025 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/tackling-tax-season-for-telehealth-providers/https://www.wingspan.app/articles/tackling-tax-season-for-telehealth-providers/How Telehealth Providers Can Simplify Tax Season—Simplify 1099 Filing with Automation to Save Hours and Eliminate ErrorsThu, 02 Jan 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/how-this-telehealth-startup-saved-80-hours-on-1099-management-with-wingspan/https://www.wingspan.app/articles/how-this-telehealth-startup-saved-80-hours-on-1099-management-with-wingspan/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.Wed, 01 Jan 2025 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/demystifying-the-1099-process-how-to-make-this-january-easy/https://www.wingspan.app/articles/demystifying-the-1099-process-how-to-make-this-january-easy/Webinar Recap: 3 Key Challenges with 1099 Filing (and How to Solve Them)Thu, 19 Dec 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/outsource-vs-automate-which-is-best-for-1099-filing/https://www.wingspan.app/articles/outsource-vs-automate-which-is-best-for-1099-filing/Why Outsourcing Isn’t the Answer for 1099 FilingMon, 09 Dec 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/how-your-onboarding-process-can-make-or-break-tax-season/https://www.wingspan.app/articles/how-your-onboarding-process-can-make-or-break-tax-season/The Secret to a Smooth Tax Season? Your Onboarding ProcessTue, 03 Dec 2024 00:00:00 GMTOnboardinghttps://www.wingspan.app/articles/watch-out-for-these-1099-filing-penalties-how-to-avoid-them/https://www.wingspan.app/articles/watch-out-for-these-1099-filing-penalties-how-to-avoid-them/What Accounting Teams Need to Know About 1099 Filing PenaltiesThu, 21 Nov 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/everything-you-need-to-know-about-1099-filing-this-tax-season/https://www.wingspan.app/articles/everything-you-need-to-know-about-1099-filing-this-tax-season/Avoid Penalties and Protect Contractor Relationships with a Streamlined 1099 Filing ProcessTue, 12 Nov 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/accounts-payable-systems-arent-designed-for-contractor-management/https://www.wingspan.app/articles/accounts-payable-systems-arent-designed-for-contractor-management/Why Vendor Payment Systems Fall Short for Contractor Management—and How to Fix ItWed, 16 Oct 2024 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/why-your-contractors-just-want-to-get-paid/https://www.wingspan.app/articles/why-your-contractors-just-want-to-get-paid/A Contractor’s Perspective on Getting PaidTue, 08 Oct 2024 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/payment-platforms-are-great--but-your-contractors-need-more/https://www.wingspan.app/articles/payment-platforms-are-great--but-your-contractors-need-more/Why Traditional Payment Processors Don’t Work for Contractor ManagementThu, 05 Sep 2024 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/why-i-joined-wingspan-with-christian-borrelli/https://www.wingspan.app/articles/why-i-joined-wingspan-with-christian-borrelli/Empowering the Future of Work: Why I Joined Wingspan to Revolutionize Contractor Payroll and ManagementTue, 03 Sep 2024 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/how-to-save-time-money-headaches-filing-1099-forms/https://www.wingspan.app/articles/how-to-save-time-money-headaches-filing-1099-forms/Streamline Your 1099 Filing: How to Tackle Tax Season Stress-Free for Your Contractors and BusinessFri, 16 Aug 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/how-to-make-contractor-payments-accurate-fast-reliable/https://www.wingspan.app/articles/how-to-make-contractor-payments-accurate-fast-reliable/The Challenge of Contractor Payments: Transforming Invoicing into Payroll EfficiencyWed, 31 Jul 2024 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/contractor-onboarding-made-simple-a-guide-for-accounting-and-finance-pros/https://www.wingspan.app/articles/contractor-onboarding-made-simple-a-guide-for-accounting-and-finance-pros/Finance and accounting experts talk 1099 onboarding best practices, red flags and more in this ultimate masterclass. Thu, 18 Jul 2024 00:00:00 GMTOnboardinghttps://www.wingspan.app/articles/why-your-next-therapist-could-be-a-freelance-and-why-thats-okay/https://www.wingspan.app/articles/why-your-next-therapist-could-be-a-freelance-and-why-thats-okay/Powering the historic growth in telehealth adoption is a rise in independent providers that can directly connect with patients through digital health platforms. Mon, 24 Jun 2024 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/how-to-tell-if-youre-misclassifying-your-workers-as-independent-contractors/https://www.wingspan.app/articles/how-to-tell-if-youre-misclassifying-your-workers-as-independent-contractors/There are a plethora of laws and guidelines you can use to determine whether you're properly classifying your workers. Mon, 22 Apr 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/lessons-from-uber-lime-meta-on-misclassifying-your-independent-contractors/https://www.wingspan.app/articles/lessons-from-uber-lime-meta-on-misclassifying-your-independent-contractors/It's easy to see why businesses are eager to work with independent contractors, but the consequences of misclassifying them can get expensive, fast. Mon, 15 Apr 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/the-ultimate-guide-to-worker-classification-in-2024/https://www.wingspan.app/articles/the-ultimate-guide-to-worker-classification-in-2024/This guide provides in-depth guidance for businesses looking to mitigate their compliance risk when working with contractors at scale. Tue, 09 Apr 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/employee-vs-contractor-misclassification-checklist/https://www.wingspan.app/articles/employee-vs-contractor-misclassification-checklist/Not sure whether to classify a worker as an employee or independent contractor? Use this IRS framework to help assess your misclassification risk. Tue, 12 Mar 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/how-one-loss-adjusting-firm-is-using-adjuster-experience-to-drive-growth/https://www.wingspan.app/articles/how-one-loss-adjusting-firm-is-using-adjuster-experience-to-drive-growth/CRU Group COO Bret Peiffer joined our Co-Founder & CTO Greg Franczyk to discuss how the innovative claims company transformed its business using Wingspan. Mon, 26 Feb 2024 00:00:00 GMTOnboardinghttps://www.wingspan.app/articles/from-strategy-to-execution-incorporating-independent-adjusters-into-your-growth-plan/https://www.wingspan.app/articles/from-strategy-to-execution-incorporating-independent-adjusters-into-your-growth-plan/Delivering a seamless adjuster experience becomes a strategic imperative for claims companies seeking to retain and grow a 1099 workforce.Tue, 13 Feb 2024 00:00:00 GMTOnboardinghttps://www.wingspan.app/articles/6-signs-your-1099-payment-processes-may-be-broken/https://www.wingspan.app/articles/6-signs-your-1099-payment-processes-may-be-broken/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. Wed, 07 Feb 2024 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/a-step-by-step-guide-to-simplifying-your-1099-filing-with-wingspan/https://www.wingspan.app/articles/a-step-by-step-guide-to-simplifying-your-1099-filing-with-wingspan/It’s time to offload your 1099 processing to Wingspan and let it own compliance on your behalf. Here's how easy it is. Thu, 18 Jan 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/a-step-by-step-guide-to-how-wingspan-simplifies-1099-filing/https://www.wingspan.app/articles/a-step-by-step-guide-to-how-wingspan-simplifies-1099-filing/It’s time to offload your 1099 processing to Wingspan and let it own compliance on your behalf. Here's how easy it is. Thu, 18 Jan 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/1099-filing-season-doesnt-have-to-suck-heres-how-to-prepare-for-a-smooth-month-end/https://www.wingspan.app/articles/1099-filing-season-doesnt-have-to-suck-heres-how-to-prepare-for-a-smooth-month-end/I learned firsthand how stressful and complicated the 1099 filing process is when I became a freelancer at the end of 2016. Tue, 16 Jan 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/wingspans-2023-year-in-review-reflections-gratitude-growth/https://www.wingspan.app/articles/wingspans-2023-year-in-review-reflections-gratitude-growth/I wanted to take a quick moment and reflect back on 2023 at Wingspan, an unforgettable year of momentum, milestones and growth.Thu, 04 Jan 2024 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/what-flexible-work-companies-should-know-about-1099-filing-before-the-january-31st-deadline/https://www.wingspan.app/articles/what-flexible-work-companies-should-know-about-1099-filing-before-the-january-31st-deadline/1099 filing season can be incredibly stressful for finance teams. Here's everything you need to know before the filing deadlineWed, 03 Jan 2024 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/everything-you-need-to-know-about-1099-filing-this-tax-season-2023/https://www.wingspan.app/articles/everything-you-need-to-know-about-1099-filing-this-tax-season-2023/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. Thu, 14 Dec 2023 00:00:00 GMTCompliancehttps://www.wingspan.app/articles/2024-edition-everything-to-know-about-1099-filing-this-tax-season/https://www.wingspan.app/articles/2024-edition-everything-to-know-about-1099-filing-this-tax-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.Mon, 11 Dec 2023 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/introducing-wingspan-2-0/https://www.wingspan.app/articles/introducing-wingspan-2-0/See how businesses use Wingspan to automate onboarding, invoicing, payments, compliance, and benefits for their clients and flexible workforce. Tue, 28 Nov 2023 00:00:00 GMTUpdateshttps://www.wingspan.app/articles/how-to-bring-the-future-of-work-back-to-the-future/https://www.wingspan.app/articles/how-to-bring-the-future-of-work-back-to-the-future/In his Forbes debut, our CEO Anthony Mironov makes the case for a paradigm shift in how companies engage with contractors at scale.Tue, 14 Nov 2023 00:00:00 GMTFuture of Workhttps://www.wingspan.app/articles/filling-financial-gaps-for-gig-workers/https://www.wingspan.app/articles/filling-financial-gaps-for-gig-workers/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 mindWed, 01 Nov 2023 00:00:00 GMTPaymentshttps://www.wingspan.app/articles/does-your-freelance-business-need-an-llc/https://www.wingspan.app/articles/does-your-freelance-business-need-an-llc/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.Tue, 21 Sep 2021 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/taking-care-of-business-carolyn-bothwell/https://www.wingspan.app/articles/taking-care-of-business-carolyn-bothwell/The brand strategist and copywriter shares the the best advice she’s ever gotten, plus the mindset freelancers must have to succeed.Wed, 18 Nov 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/taking-care-of-business-with-lizzie-bildner/https://www.wingspan.app/articles/taking-care-of-business-with-lizzie-bildner/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.Thu, 15 Oct 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/taking-care-of-business-with-sarah-hussaini/https://www.wingspan.app/articles/taking-care-of-business-with-sarah-hussaini/The architect turned ceramicist is the founder of Not Work Related, a Brooklyn-based housewares company.Mon, 31 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/how-to-take-paid-parental-leave-when-youre-self-employed/https://www.wingspan.app/articles/how-to-take-paid-parental-leave-when-youre-self-employed/How to Manage Parental Leave with ContractorsWed, 26 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/indrani-stangl-on-how-to-be-productive-when-work-slows-down/https://www.wingspan.app/articles/indrani-stangl-on-how-to-be-productive-when-work-slows-down/A career coach shares her best tips.Mon, 24 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/taking-care-of-business-with-ben-johnson/https://www.wingspan.app/articles/taking-care-of-business-with-ben-johnson/The photographer, videographer, and composer produced the award-winning documentary “Big Charity."Wed, 19 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/out-of-office-how-to-take-paid-time-off-self-employed/https://www.wingspan.app/articles/out-of-office-how-to-take-paid-time-off-self-employed/Bonus: Your health and your productivity will soar.Mon, 17 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/how-to-write-a-proposal-that-will-land-you-new-business/https://www.wingspan.app/articles/how-to-write-a-proposal-that-will-land-you-new-business/Five foolproof ways to sell your services to a prospective client.Wed, 12 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/stop-self-sabotaging-behavior/https://www.wingspan.app/articles/stop-self-sabotaging-behavior/Advice from experts that help small business owners navigate (and overcome) seven thought patterns that can undermine our work.Wed, 05 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/how-to-get-your-ppp-loan-forgiven/https://www.wingspan.app/articles/how-to-get-your-ppp-loan-forgiven/Here’s what you need to know about the low interest loan from the government.Mon, 03 Aug 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/how-to-apply-for-government-support-through-the-sbas-economic-injury-disaster-loan-program/https://www.wingspan.app/articles/how-to-apply-for-government-support-through-the-sbas-economic-injury-disaster-loan-program/Everything you need to know about pandemic-related aid.Wed, 29 Jul 2020 00:00:00 GMTFor Contractorshttps://www.wingspan.app/articles/how-to-use-social-networking-sites-to-find-work/https://www.wingspan.app/articles/how-to-use-social-networking-sites-to-find-work/These groups provide advice, collaboration, and even a source of new jobs.Mon, 27 Jul 2020 00:00:00 GMTFor Contractors