Kick Profile: Founders, Funding History and Backers

Kick, the Palo Alto bookkeeping startup founded by Conrad Wadowski, has raised $20 million in total, including a $9 million seed round in October 2024 and a Series A in November 2025 co-led by Felicis and GV.

The company sells what it calls self-driving bookkeeping to small business owners and their accountants. It says more than 5,000 business owners and accountants now use the product.

For finance professionals the question is where Kick sits among AI bookkeeping tools. It is self-serve software rather than an outsourced service, and its entry price is $40 a month billed annually, with a free tier. That puts it in a different position from done-for-you rivals such as Pilot and its alternatives, which charge from $99 a month for bookkeeping alone.

Kick funding: $20 million from four named backers

Kick announced a $9 million seed round in October 2024. General Catalyst and the OpenAI Startup Fund led it, and the company’s own announcement says the money came from OpenAI, General Catalyst and more than 50 angel investors.

The angels include people with backgrounds at Stripe, Notion and Square. The announcement names Lachy Groom, Scott Belsky, Emily Kramer, Austen Allred and Sahil Lavingia among them.

The OpenAI link is therefore sourced. The investor is the OpenAI Startup Fund, a venture vehicle, and Kick names it on its own site as a backer of both rounds.

The second round came in November 2025. Wadowski announced that Kick had raised $20 million in total, with Felicis and GV, formerly Google Ventures, joining General Catalyst and the OpenAI Startup Fund. Kick’s homepage now carries the headline “Kick has raised $20M to build the future of accounting“.

The company has not published the size of the Series A on its own pages. The $20 million figure is the cumulative total, and Accountio’s Kick vendor profile lists the funding across four rounds, only two of which are described in detail.

Kick has not disclosed a valuation, revenue or annual recurring revenue.

Who founded Kick and what he built before

Wadowski is founder and chief executive. He previously co-founded Teachable, the online course platform, and has described Kick as the product of his own experience running businesses.

“When I first became an entrepreneur I was surprised to learn my #1 expense wasn’t contractor or ads, it was taxes,” Wadowski wrote in the funding post on Kick’s site.

That origin shapes the product. Kick is aimed at owners who want clean books and tax-ready numbers without hiring a bookkeeper, and it gives their accountant a workspace to review the output.

Accountio’s profile lists Adrian Ślipko as a co-founder and gives 2021 as the founding year. Kick’s own pages emphasise Wadowski as the public face of the company.

What Kick does: the agentic ledger

Kick describes itself on its homepage as “the agentic ledger that does your books with you”. The software categorises transactions in real time, with review by human experts, and flags easy-to-miss deductions such as home office, vehicle and travel costs.

It produces revenue and spending insights, multi-entity journal entries, and tax-ready profit and loss statements and balance sheets that can be shared with an accountant. Bank and card feeds supply the transactions.

Kick does not file tax returns. It prepares a year-end package for the owner’s CPA, which keeps the product on the bookkeeping side of the line and leaves filing to the accountant.

A partnership with FreshBooks brings the product to that platform’s US customers. The market Kick serves is the United States, which matters for readers in the UK and EU weighing it against local tools.

Who Kick is for and what it costs

Testimonials on the site come from a pest control company, an architect, a web designer, a multi-business owner and a CPA firm owner. The pattern is small, owner-run businesses and the accountants who serve them, rather than mid-sized finance teams.

Pricing is published, which is not universal among venture-backed rivals. The free plan covers one entity and 250 transactions a year.

• Basic: $40 a month, billed annually
• Plus: $100 a month, billed quarterly
• Advanced: $300 a month

The multi-entity journal entries matter to owners who run several businesses. They also matter to accountants managing related companies, who otherwise reconcile each entity by hand.

For firms, the practical use is as a client-side tool. A client who keeps books in Kick can hand over a package for the year-end, and the accountant reviews rather than builds. That fits the wider shift described in AI accounting tools by task, where categorisation and extraction are the most mature uses.

How Kick compares with Pilot and other AI bookkeeping tools

The clearest contrast is with Pilot, the best-known name in outsourced startup bookkeeping. Pilot delivers bookkeeping, tax and CFO support through an AI-assisted team, while Kick is software the owner or an accountant operates. Details of Pilot’s rounds are on Accountio’s Pilot funding page.

Accountio’s comparison puts Pilot’s total funding at more than $150 million, against Kick’s $20 million, and its customer base at more than 3,500 startups and small businesses, against Kick’s 5,000 and more. Pilot was founded in 2017.

The price gap follows the service gap. Pilot’s plans start at $99 a month for bookkeeping essentials and $299 a month for core bookkeeping billed annually, with tax filing from $1,000 a year and CFO services from $1,750 a month. Kick’s top tier is $300 a month.

Other AI bookkeeping tools sit nearer Kick’s end of the market or target accounting firms directly. Double sells AI bookkeeping to firms, and Outmin serves small and medium-sized businesses. Readers weighing live deployments rather than pilots can use Accountio’s guide on AI accounting tools in production.

The trade-off is control against convenience. Kick gives the owner a ledger and an AI to maintain it, with experts checking categorisation. Pilot takes the work away entirely, at a higher monthly cost.

What to watch at Kick

Kick has not published figures on accuracy, error rates or the share of transactions that human reviewers change. Those numbers would show how far the books are self-driving in practice.

Its homepage and funding post are the main public record of the company’s progress. The next test is whether the 5,000-plus user count grows enough to justify a further round, and whether Kick extends beyond the United States, where it currently operates.