Puzzle
San Francisco, US · Founded 2019 · 90 employees on LinkedIn · 13 known investors
Puzzle builds a modern accounting system for startups and small-to-medium businesses, delivering real-time financial intelligence by reconstructing core ledger and data infrastructure. The platform replaces legacy accounting software with AI-era capabilities designed to make financial data trustworthy and actionable.
Also known as Puzzle Financial · Puzzle.io
Founders & leadership
Puzzle was founded in 2019 by Sasha Orloff and John Cwikla.

Board

Investors · 13
Also in the syndicate · 3
Funding
SEC filings, press & company announcements$52.1M disclosed across 2 rounds · 2021–2023
- Undisclosed amountSeries AFeb 2023Source ↗
▶$30.5MraisedNov 2023 · 21 investors · OtherRule 506(b)
- Sasha OrloffExecutive Officer, Director
- Hemant TanejaDirector
- Offering amount
- $30.5M
- Amount sold
- $30.5M
- First sale
- Oct 2023
- Incorporated
- Corporation, Delaware, 2019
- Federal exemptions
- 06b
▶$21.5MraisedJun 2021 · 32 investors · Other TechnologyRule 506(b)
- HEMANT TANEJADirector
- Sasha OrloffExecutive Officer, Director
- Offering amount
- $21.6M
- Amount sold
- $21.5M
- First sale
- May 2021
- Incorporated
- Corporation, Delaware, 2019
- Federal exemptions
- 06b
Source: SEC EDGAR Form D. Amounts as filed; amended filings shown once at their latest values.
Company profile
researched Aug 2026Puzzle is an accounting software company that has rebuilt the general ledger and surrounding data infrastructure rather than layering automation on top of legacy systems such as QuickBooks or Xero. The platform ingests transaction data directly from financial tools and converts it into reconciled journal entries and financial statements, producing income statements, balance sheets and cash activity reports automatically from raw data. It supports both cash and accrual accounting from the same ledger, and continuously updates metrics including cash, burn rate, runway, ARR/MRR and revenue accruals rather than only at period end.
The current product positions AI agents as the primary workers on the ledger: agents draft transaction categorization, reconciliation and close steps for human review, with the company stating that nothing posts without user approval and that workflows are designed by the accountant. Puzzle markets to two segments — accounting firms seeking to serve more clients without adding headcount, and startups/SMBs seeking daily visibility into their numbers. Company claims include up to 98% automated categorization, automation of 85–95% of repetitive bookkeeping work, and up to 50% faster month-end close. Native integrations named include Stripe, Brex, Mercury, Ramp, Deel, Gusto, Rippling and Pulley.
At the time of its November 2023 funding announcement, Puzzle described itself as a generative accounting platform that had launched publicly roughly a year earlier and was growing new customers 15% month over month. A third-party profile records 700+ customers and $13 billion in transactions categorized as of July 2023, up from 500 customers and $10 billion in January 2023; the company's own site currently cites 7,000+ accounting firms and startups.
Founding story
Cofounders Sasha Orloff (CEO) and John Cwikla (CTO) started Puzzle on the premise that accounting is too important to be an afterthought and that most accounting software was designed decades ago for manual workflows, disconnected systems and hindsight reporting. Their stated aim was to build an accounting system for the AI era by rebuilding core data, agent and general ledger infrastructure so financials are real-time and accurate while accountants remain in control. Orloff was previously a co-founder of Mission Lane and Cwikla previously founded The Giant Pixel Corporation.
Business model
Software product sold to businesses and accounting firms, with a free entry tier ("Get started for free") alongside demo- and sales-assisted onboarding for firms and larger customers. Puzzle also references a network of on-demand accounting and tax experts and an accountant network available to users.
The sources do not state pricing or specific revenue mechanics beyond a free-to-start offering and paid product motion implied by demos and firm-level plans.
Traction
Company website states 7,000+ accounting firms and startups use Puzzle. A third-party profile reports 700+ customers and $13 billion in transactions categorized as of July 2023 (up from 500 customers and $10 billion in January 2023). The company reported 15% month-over-month new customer growth and rapid double-digit monthly growth as of November 2023. Published case studies cite outcomes such as Burkland cutting month-end close by 25%, Accountalent saving 3+ hours per client per month, and Decimal migrating hundreds of clients to Puzzle.
Latest developments
The current website presents Puzzle as an agentic accounting core with AI agents handling categorization, reconciliation and an "AI Close" workflow, migration tooling from QuickBooks, and a dedicated offering for accounting firms; it cites 7,000+ firms and startups on the platform and references SOC 2 compliance.
▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies
Market position
Puzzle positions itself as an alternative to legacy accounting suites (QuickBooks, Xero) and compares itself to Digits. Its 2023 funding announcement framed the company as the "first generative accounting platform" and argued that competitors bolt AI onto existing software while Puzzle rebuilt the ledger.
Rebuilt core general ledger and data infrastructure rather than an AI layer over legacy software; continuous rather than month-end bookkeeping; deterministic, review-gated agent output ("same inputs, same outputs, every run", nothing posts without approval); cash and accrual views from one ledger; native source-level integrations instead of imports or syncs.
Technology
A proprietary AI-native general ledger and real-time data platform rebuilt from the ground up, combined with an agentic layer that drafts categorization, reconciliation and close activities for human review. The company argues that building agents on top of legacy accounting APIs is limiting, so it built the agent platform and ledger together. Direct integrations with payment, spend, banking, payroll and cap-table tools (Stripe, Ramp, Brex, Mercury, Gusto, Rippling, Deel, Pulley) feed the ledger. The site references SOC 2 compliance and emphasizes auditability and transparency of AI activity.
Go-to-market
Self-serve sign-up plus sales-assisted motions ("book a demo", "chat with an expert"), a partner/channel motion through accounting firms (Burkland, Attivo Partners, Decimal, Accountalent, Parallel, Central), co-marketing with fintech partners such as Brex, Ramp and Mercury, published customer case studies, and migration tooling that imports history from QuickBooks.
Startups, small and medium-sized businesses, and accounting firms — including firms providing Client Advisory Services — as well as founders and finance teams that need investor-ready financials and due-diligence metrics.
Geography
Headquartered in San Francisco, California; the sources do not describe operations outside the United States, though references to U.S. accounting norms (GAAP, IRS, CPA) indicate a U.S. focus.
History
Puzzle was incubated with General Catalyst's Creation Fund and launched its platform publicly in July (about one year before its November 2023 announcement). It raised an oversubscribed $30 million round in November 2023 led by S32 and XYZ Capital, bringing total disclosed funding at that time to $50 million. The product has since shifted its positioning from "generative accounting" toward an agent-based accounting core serving both startups/SMBs and accounting firms.
Risks & controversies
Sources disclose no controversies. Notable data caveats: a third-party profile lists total raised as $20 million while the company's own announcement states $50 million as of November 2023, and most performance figures (automation rates, close-time reduction, user counts) are company-reported and unaudited.
Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Founder mafia
2 people who came through Puzzle went on to found or lead other companies.
Competitors · 8
by search overlapCompanies competing with Puzzle for the same Google search keywords, organic and paid, via search-intersection analysis.
Timeline · 3
launches, deals, and filingsPuzzle announced $30 million in new, oversubscribed funding led by S32 and XYZ Capital, with participation from General Catalyst, FOG Ventures, Felicis, Kapor Capital, Sterling Road, Born Ventures, Soma Capital, Alumni Ventures, Gaingels and 50+ CFO and operator angels, bringing total funding to $50M.
$30M source ↗
Puzzle's funding announcement states the company was incubated with General Catalyst's Creation Fund.
Puzzle publicly launched its platform in July; by November 2023 the company reported one year since launching publicly and double-digit monthly growth.
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
In the news
Data digest: Pokémon Go, Rust, Mihoyo and Bluey stats plus funding news, puzzle market analysis and more – Mobilegamer.bizmobilegamer.biz · Jul 2026
Turkish Mobile Gaming Startup Bold Games Raises $6 Million to Expand Puzzle Game Across Global Marketsarabfounders.net · Jul 2026▸Research sources · 8
primary sources listed
- Puzzlepuzzle.io · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Puzzle do?
- Puzzle builds an AI-native general ledger and accounting platform for startups, SMBs and accounting firms.
- Who founded Puzzle?
- Puzzle was founded by Sasha Orloff, John Cwikla in 2019.
- Who are Puzzle's investors?
- Puzzle's investors include Felicis Ventures, Fjor Founders, Kapor Capital, On Deck, Sterling Road, Two Culture Capital, Village Global, XYZ Venture Capital and 2 more.
- How much funding has Puzzle raised?
- Puzzle has disclosed $52.1M raised across 2 rounds.
- Where is Puzzle headquartered?
- Puzzle is headquartered in San Francisco, US.



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