Puzzle (puzzle.io) is AI accounting software. The company describes it as "a modern ledger that delivers real-time, accurate financials while keeping accountants firmly in control" (puzzle.io/about). Sasha Orloff is CEO and co-founder. In November 2023, Puzzle announced a $30M raise, bringing total funding to $50M at the time (Puzzle announcement, Nov 14, 2023). StartupCookie worked with Puzzle for two years, through the end of 2025: executive content under Sasha Orloff's byline, customer case studies for the Puzzle blog, and production support for Tech Finance, the podcast Sasha hosts.
The challenge
AI accounting software asks accountants to trust a system that touches their core work. Puzzle's answer to that tension sits in its own product description: real-time, accurate financials, with accountants firmly in control.
A position like that cannot live only on a homepage. It carries more weight when the CEO argues it in public, in long form, under his own name, and when named customers describe how they actually run their financials on the product. Puzzle brought in StartupCookie to produce both, and kept the engagement running for two years.
What we did
Executive long-form under Sasha Orloff's byline
We produced "Our Continued Commitment to Accounting Firms", published Oct 28, 2025 on the Puzzle blog. It puts the company's position on accounting firms in the CEO's own voice, on Puzzle's own domain, where firms evaluating the product will look first.
Customer case studies
We wrote "How Paradigm (YC W24) Simplified Financial Management with Puzzle", published Feb 4, 2025. A named customer, a real workflow, on the record.
Production support for the Tech Finance podcast
Sasha hosts Tech Finance, a podcast produced with Turpentine. StartupCookie handled the operations behind guest episodes: coordinating guests and their comms teams, moving episodes from recording through review to release, and lining up the promotion on both sides for each launch. Episode after episode shipped on schedule through the end of 2025.
Results
The published work is live on puzzle.io:
- "Our Continued Commitment to Accounting Firms", executive content under Sasha Orloff's byline, published Oct 28, 2025.
- "How Paradigm (YC W24) Simplified Financial Management with Puzzle", customer case study, published Feb 4, 2025.
- Tech Finance episodes shipped on schedule, with guest coordination and launch promotion handled by StartupCookie.
Blog posts on a company domain do not carry public engagement counters the way LinkedIn posts do, so there are no reaction counts to cite here. The result we point to instead: Puzzle renewed this work month after month for two years.
Services used
Frequently asked questions
What does Puzzle do?
Puzzle is AI accounting software. The company describes it as a modern ledger that delivers real-time, accurate financials while keeping accountants firmly in control. Sasha Orloff is CEO and co-founder. Puzzle announced a $30M raise in November 2023, bringing total funding to $50M at the time.
What did StartupCookie deliver for Puzzle?
Executive long-form content under CEO Sasha Orloff's byline, customer case studies for the Puzzle blog, and production support for the Tech Finance podcast: guest coordination, episode logistics, and launch promotion. The engagement ran for two years, through the end of 2025. The published pieces are linked in this case study.
Why are there no engagement metrics in this case study?
Because there are none we can verify publicly. The deliverables are blog posts on puzzle.io, and company blogs do not show public reaction counts. We only publish numbers you can check yourself. Business-outcome numbers will be added once they are verified and Puzzle signs off.