Track1099 by Avalara

Track1099 makes it easy to e-file and e-deliver ~40 different informational tax forms, including the ubiquitous 1099-NEC (for payments to contractors) and 1099-MISC (for all sorts of things) and the increasingly-widespread 1099-K (sent by marketplaces and payment processors to their merchants). We opened for business way back in 2011, and the business has grown considerably every year since then. We're a small team (3 engineers, ~6 total people) acquired last year into a very large organization, and to a surprising extent it's the best of both worlds. We have kept our server-side up to date, currently running Rails 7 and Postgres 14. On the front end we have emphasized stability and our progressive investment in dozens of large, complex forms--it's traditional ERB with Backbone.js forms and a couple SPA-style islands. We expect to (finally) start upgrading to Hotwire or React islands soon. Probably will never go full SPA. If you like having an office, Avalara headquarters are in Seattle, WA and we have 20 other offices around the world.