tax-software
(15)
Drake Software gives April its time back
A payroll shortcut became a business serving more than 70,000 tax professionals. Now Drake is chasing the minutes lost between the return, the signature, and the payment.
TaxAct and the price of being inconvenient
A tax-software company made itself troublesome by making filing cheaper. Its next act asks a different question: how much help would you like with that?
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 Coin That Moved. The Cost That Vanished.
A coin can cross five wallets in an afternoon. Its purchase price rarely travels with it. CoinTracker made that missing number a business - first for investors, then for the institutions that serve them.
The Tax Return Was Only the First Clue
A conversation about one terrible tax form became an Indian filing service. Then GST arrived, and ClearTax discovered the more valuable problem was everything that happened before a return was filed.
The Dog Walker’s Poop Bags and the Tax Code
Keeper began by asking freelancers whether everyday purchases were really business expenses. It grew into a tax service built around an awkward truth: the best deduction finder is little help if the return still has to be finished somewhere else.
Crunch’s lesson in scale: keep the accountants close
The UK accounting company pairs software with people who can explain the numbers. Its experiment with outside accountants shows why that second half deserves as much attention as the code.
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.
TaxSlayer Built a Tax-Software Business by Charging for Help, Not Complexity
The Augusta company turned an in-house tool into a two-sided tax platform used for millions of returns. Its most copyable idea is simple: keep the forms broad, then let customers pay for the amount of human help they want.
H&R Block
H&R Block built a national habit out of one annual deadline. Now the 70-year-old tax company is teaching its storefront network, software and AI to work as one - while trying to earn trust long after April 15.
Harness (Harness Wealth)
Harness (Harness Wealth) is a New York fintech that pairs software with a curated marketplace of vetted tax, financial and estate advisors, aimed at people with complex finances - startup founders, equity-holding employees, business owners, crypto investors and other 'builders.' It combines a vertical SaaS platform that powers collaboration between tax advisors and their clients, a marketplace to discover specialist firms, and consumer tools for tracking equity and net worth. Founded in 2018 by David Snider, the former CFO/COO of Compass, the company has raised roughly $40M and grew revenue by more than 1,500% between 2021 and 2024.
Lili
Lili is a New York-based financial technology company that runs an all-in-one business banking platform for small businesses. It bundles a fee-free business checking account with built-in accounting, expense management, invoicing, automated tax savings and high-yield savings - collapsing tools that owners would otherwise stitch together. Founded in 2018 by Lilac Bar David and Liran Zelkha, Lili started serving freelancers and solopreneurs and has since repositioned toward growing, multi-employee small businesses. Banking services are provided through partner bank Sunrise Banks, N.A., Member FDIC.
Intuit
Intuit is a global financial technology company that builds software to help consumers and small businesses manage money, taxes and growth. Founded in 1983 around Quicken, it now runs four flagship platforms - TurboTax for tax filing, QuickBooks for small business accounting, Credit Karma for consumer credit and finance, and Mailchimp for marketing - reaching roughly 100 million customers worldwide. In 2026 the company is rebuilding its products around an AI-driven expert platform anchored by Intuit Assist, its generative-AI financial assistant.
Lilac Bar David
Lilac Bar David is the co-founder and CEO of Lili, a New York based financial platform that folds banking, invoicing, accounting and tax tools into a single app for small business owners. A banking and payments veteran of roughly two decades, she previously co-founded Pepper, Israel's first mobile bank, before launching Lili in 2018-2019 with Liran Zelkha. Under her leadership Lili has served hundreds of thousands of freelancers and small businesses, raised about $80 million from investors including Group 11 and Foundation Capital, and in recent years built out an Accountant AI tool while shifting focus toward larger, multi-employee businesses.
Town
Town is a San Francisco AI startup building a personal AI assistant - your 'Townie' - that plugs into the tools you already use (email, calendar, Slack, docs, WhatsApp, desktop and web), learns how you work, and proactively does the work for you. Founded in late 2024 by former Plaid CTO Jean-Denis Greze and ex-Google applied-AI director Tony Vincent, Town launched in 2025 as an AI-driven tax-and-compliance service for small businesses, then widened into a general-purpose assistant. It exited beta in June 2026 alongside a $55M Series A led by Andreessen Horowitz.