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Puzzle

“Can an AI-native, real-time general ledger built on modern fintech rails displace QuickBooks as the accounting system of record for the next generation of startups and SMBs?”

Founded2019
HQSan Francisco, California, USA (with office in Wilmington)
FoundersSasha Orloff, John Cwikla
Total raised$51.5M
Latest roundSeries A, 2023
IndustryHorizontal SaaS / Accounting
The story

Founded 2019 by ex-LendUp CEO Sasha Orloff, Puzzle launched publicly in 2023 as a modern, real-time general ledger positioned as the QuickBooks alternative for venture-backed startups running on Stripe, Mercury, Ramp, Brex, and Gusto. In 2025 it pivoted decisively toward AI, launching the Puzzle AI Suite of accounting agents (Chat, Cowork, Close) and rebranding around 'AI-native accounting.' In 2026 it stretched again with Puzzle 2.0, bundling the software with vetted accounting firm partners — moving from pure SaaS into a software+services model competing directly with Pilot and Bench.

Last 12 months
2025
2026
Product timeline
2019
Puzzle Financial Inc. founded by Sasha Orloff and John Cwikla· pivot
2022
Launched at TechCrunch Disrupt Startup Battlefield 2022 as a QuickBooks alternative for startups· banking
2023
Public launch of smart accounting software + $15M Series A led by General Catalyst· banking
2025
Launched Puzzle AI Suite (Chat, Cowork, Close agents) targeting accounting firms· pivot
2026
Puzzle 2.0 — combining software with a real accounting firm service tier (Expert Reviewed + Full Service bookkeeping)· pivot
The stack
5 layers disclosed in Puzzle’s embedded-finance stack
Payments / PSP
Stripe
Banking / BaaS
in the full report
Payroll
in the full report
Open banking
in the full report
Spend / AP
in the full report
Accounting gap: none
4 more providers across 4 layers, with confidence-scored evidence and source URLs, are in the Embedded Finance Index report.