Wingspan

Wingspan is a payroll, benefits, and onboarding platform that focuses predominantly on companies relying on independent contractors. Wingspan aims to consolidate various tools used by mid-market businesses into an all-in-one platform that links payroll, benefits, and onboarding for freelancers. It provides onboarding and management tools, performs background checks, and enables same-day payments. Employers get automated workflows for generating and filing contractor 1099 tax forms and can offer contractors discounted insurance through the platform. Wingspan also uses AI and machine learning to streamline tasks like categorizing expenses.

The contractor benefits offered by Wingspan include tax withholdings and payments; income and expense tracking; invoicing; and health, vision, and dental insurance. Wingspan also offers concierge support for financial and legal issues as well as telemedicine and prescription savings. The platform’s onboarding services include automated compliance with tax and other regulations and transparent payment services.

Wingspan uses a subscription-based business model, generating revenue per monthly active payees (MAPs), priced at USD 8-10 per month per individual. 

Key customers and partnerships

As of March 2023, Wingspan claimed to have hundreds of enterprise clients and over 20,000 members on the platform. The company serves a broad and diverse customer base that relies on freelancers as a critical part of its workforce.

The platform offers integration with accounting software like QuickBooks, Xero, Sage, NetSuite, FreshBooks, and Zoho Books, as well as HR software like Gusto HR, ADP, Rippling, Namely, BambooHR, and DocuSign. Wingspan allows for Single Sign-On (SSO) and Two-Factor Authentication (2FA) through a single set of credentials such as okta and Google. The platform also enables users to sync invoices, payables, and contractors from their existing project management systems like Airtable and Google Sheets. Moreover, Wingspan provides an open API for custom integrations.

Funding and financials

In March 2023, Wingspan raised USD 14 million in a Series A funding round led by Andreessen Horowitz (a16z). The fresh funds were allocated for product expansion and hiring, as it planned to double its 20-person team by the end of the year.