tax-compliance
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Digital River made selling easy. Getting paid was harder.
For three decades, Digital River took the paperwork out of selling across borders. Its shutdown exposed the risk hiding between a successful checkout and money in the bank.
David Rosas and the 23-year promise of payday
He co-founded Greenshades to tackle payroll taxes, then spent 23 years leading its expansion. His next assignment: helping a new CEO take over the company he helped build.
RSI and the art of making taxes less taxing
Behind a simple tax payment sits a very complicated machine. RSI helps governments rebuild it, one rule, record, and revenue stream at a time.
HdL Companies finds the money cities missed
A former city manager turned a neglected spreadsheet problem into a national business. HdL’s proposition is wonderfully practical: check the revenue you are already owed before asking for more.
2Checkout and the Strange Business of Making Buying Boring
A software seller can reach the world with a download. Getting the world to pay, renew and satisfy the tax authorities is where 2Checkout earns its keep.
PowerPlan and the second life of a power line
A utility can finish building long before its accountants finish the job. PowerPlan has built a business in that expensive interval, turning physical assets into financial records that tax teams and regulators can use.
Tax Technologies and the art of selling yesterday
Before asking a company to buy Tax Series, Tax Technologies offers to reproduce a year of its tax work. In a business devoted to calculating the future, yesterday makes a surprisingly persuasive sales pitch.
The $40 Million Feature Hiding in Plain Sight
Salsa thinks the largest bill in a small business should live inside the software that already understands the business. Its trick is not making payroll disappear - it is deciding who should have to see the machinery.
The Government Form That Refused to Die
GovOS made a business out of the chores citizens notice only when they go wrong - permits, records, taxes, signatures and payments. Its rise, and one costly migration that did not work, explain both the promise and the limits of digital government.
The $800 Million Bet on Making the Invoice Disappear
Thomson Reuters bought Pagero for roughly $800 million because Europe’s invoice is becoming a live tax report. The prize is not prettier paperwork - it is a network that makes the paperwork vanish into the workflow.
The Tax Man Got an API. Sovos Built the Plumbing for Everyone Else.
Governments now inspect transactions in real time. Sovos sells the software layer that keeps invoices moving, taxes calculated and finance teams out of the penalty box - across nearly 200 countries.
The Payroll Company Betting Your Weirdest Pay Run Should Stay In-House
Greenshades spent two decades turning tax software into a control panel for messy American payroll. Its best customers are not looking for fewer knobs - they need the right ones.
Ryan Built a $1.24 Billion Business Finding Money Companies Left Behind
The tax specialist started on credit cards, nearly lost a star employee to its work culture, and then rebuilt both the office and the product. Today, Ryan says it serves 74,000 clients and recovered more than $4 billion for them in a single year.
Andrew Rea Found a Startup in the Fine Print
He went from construction shifts and grocery deliveries to venture capital, startup operations and a $25 million tax company. The useful part of Andrew Rea’s story is how often the unglamorous work became the opportunity.
ZenLedger Bet on Crypto's Boring Part - and Found the Durable Business
Coins soar, exchanges vanish, and the tax bill still arrives. ZenLedger built a business around the stubborn work left behind: finding cost basis, reconciling transactions and turning crypto chaos into forms an accountant can actually use.
Your Bill Pay Stack Wasn't Built for a Crowd
BILL, Stampli, Melio and AvidXchange can move vendor money across borders. Tipalti starts from a different problem: onboarding and paying a changing crowd of creators, affiliates and marketplace sellers at global scale.
Mazeed Wants to Be the Finance Department in Every Small Business Owner's Pocket
The Dubai fintech is betting that Gulf businesses do not want another blank accounting dashboard. They want software that knows the rules - and a human expert when the rules get complicated.
FastSpring Sells the Software So Its Makers Don’t Have To
A checkout is the visible inch of a global sale. FastSpring takes responsibility for the tax filings, payment routes, subscription logic and buyer support underneath it - becoming the seller on paper so digital companies can keep building.
The Startup Teaching Governments to Read the $20 Trillion They Can't See
Most financial crime hides in plain sight, scattered across the open web. IVIX built an AI platform that reads all of it at once - and hands governments a map.
ADP
Founded to hand-process payroll for a handful of New Jersey firms, ADP now quietly moves the paychecks of one in six American workers - and it hasn't missed a quarterly earnings increase since 1961.
Avalara
Avalara built a large software business by hiding one of commerce's least-loved chores inside the systems companies already use. Now it wants AI agents to calculate, classify and file without waiting for a human to open the tax screen.
Eazipay
Eazipay is a Lagos-based payroll and payment automation platform that lets African businesses run payroll, remit taxes and statutory contributions, and pay their teams in about five minutes. Founded in 2021 and backed by Y Combinator (W22), it also offers payroll APIs for banks and neobanks and financial-wellness tools such as early wage access for workers.
Compt
Compt is a Boston-based HR software company that runs flexible employee stipends and Lifestyle Spending Accounts (LSAs) for employers. Instead of one-size-fits-all perks, employees choose how to spend an allowance across categories like wellness, professional development, childcare, home office and pet care; they submit a receipt and get reimbursed through payroll with the correct tax treatment applied automatically. Founded in 2018 by Amy Spurling, the reimbursement-based platform emphasizes IRS-compliant tax handling, high participation, and low administrative overhead, and operates across all 50 U.S. states and 75+ countries.
Taxbit
Taxbit builds compliance infrastructure for the digital economy - software that turns messy on-chain and off-chain transaction data into accurate tax forms, regulatory filings, and audit-ready accounting. Founded in 2018 by CPAs, tax attorneys, and engineers, the company automates digital-asset tax information reporting (1099-DA, DAC7, CARF, 1042-S) and subledger accounting for exchanges, banks, enterprises, and government agencies, reportedly generating 100M+ tax forms and reconciling hundreds of billions of dollars in transactions.
doola
doola is a New York-based fintech that helps entrepreneurs anywhere in the world start and run a U.S. business. Its 'Business-in-a-Box' platform bundles LLC and C-Corp formation, EIN registration, U.S. business banking access, bookkeeping, tax filing, compliance and e-commerce analytics into one back office, plus an AI Co-Founder. Founded in 2020 and backed by Y Combinator, doola has served 15,000+ founders across 175+ countries and is pushing agentic company formation directly into tools like ChatGPT, Claude, Replit, Lovable and Vercel.
Dots
Dots is a San Francisco-based global payouts infrastructure company that lets marketplaces, platforms, and service businesses pay workers, sellers, and creators anywhere through a single end-to-end API. One integration unifies bank transfers, PayPal, Venmo, Cash App, and stablecoins, and bundles recipient onboarding, KYC/anti-fraud, and tax form collection so platforms can move money to over 1 million payees across 190+ countries without building payment rails themselves.
Neo.Tax
Neo.Tax is an AI software company that automates the R&D tax credit and software capitalization for startups, SMBs, and enterprises. Its platform deploys a set of AI agents trained on IRS code, regulations, and case law to passively read engineering and financial data from systems like GitHub, Jira, payroll, and the general ledger, then produce audit-ready tax filings under IRC Section 41, Section 174, and ASC 350-40. Founded by a former Intuit product manager, a Stanford machine-learning PhD, and a former IRS R&D audit agent, Neo.Tax turns one of the most painful, manual processes in corporate tax into something close to a continuous, automated workflow.
Wingspan
Wingspan is a New York-based payroll and management platform built specifically for the 1099 contractor workforce. It automates the full contractor lifecycle - onboarding, W-9 verification, background checks, same-day payments, tax withholding, and automated 1099 filing - and now ships that stack as an embeddable, white-label API (Wingspan Embed) for HR, HCM, and PEO platforms. The company has processed more than $3 billion in contractor payments and counts Teladoc Health and CRU Group among its customers.
Lumanu
Lumanu is a fintech platform built for the creator economy that lets enterprise brands and agencies pay influencers, creators, freelancers and other vendors anywhere in the world. By acting as a single 'master vendor of record', Lumanu absorbs the administrative burden of onboarding, tax compliance (W-9s, 1099s), and global multi-currency payouts, so marketing teams move faster while finance teams keep control and compliance. The company has processed well over $1 billion in creator payments and onboarded hundreds of thousands of vendors.
Warp
Warp is an AI-native payroll, compliance, and benefits platform built for high-growth startups. It automates the back-office grind - multi-state tax registrations, filings, benefits enrollment, global contractor payments, and compliance-notice resolution - so founders can hire, onboard, and pay teams anywhere in the US and 150+ countries without the manual admin. Backed by Y Combinator and Sound Ventures, Warp has raised about $24-25M to build what it calls an autonomous back office.