Sasha Orloff

About Sasha Orloff

I’m Sasha Orloff. Married, father of two, and cofounder & CEO of Puzzle.I’m not a CPA. I’m a modeler.For 20+ years, I’ve focused on how data, analytics, and systems shape better decisions. Companies I’ve founded have raised $1B+ in venture capital and debt, and Puzzle. founded in 2019. is the most ambitious yet.What I’ve learned is simple:If your inputs are wrong, your outputs are fiction. That belief is what led me to accounting.Most businesses still operate on financial truth that arrives 30–60 days late. AI doesn’t fix that problem. it accelerates it. At Puzzle, we’re building a modern core accounting platform (the general ledger), designed for provable accuracy and long-overdue automation.We take an accountant-first approach because clean, real-time data is the foundation for every forecast, dashboard, and AI insight. When accounting runs in real time, finance stops being a bottleneck and becomes a competitive advantage.I also host the Tech Finance Podcast on a16z Studios, where I speak with founders and finance leaders about how successful companies actually architect growth, capital, and decision-making.(Available on Spotify, Apple, and YouTube.)Over the years, I’ve worked across startups, multinationals, governments, and non-profits — as an operator, entrepreneur, advisor, and board member, always focused on building durable systems, not demos.I’ve been a guest lecturer at Stanford, Princeton, Georgetown, UC Berkeley, Hult, and Harvard, and have spoken at TEDx, the World Economic Forum, Money2020, TechCrunch Disrupt, the Milken Institute Global Forum, and more.My work has been featured in WSJ, NYT, FT, CNN, Bloomberg, TechCrunch, Wired, Fortune, Fast Company, and others.Outside of work, life is simple: mornings with my kids, a weekly date night with my wife (20 years and counting), and weekends hiking, soccer, and family time.I use this space to write about building companies, AI in accounting, fundraising, and what actually works when scaling finance teams and firms.P.S. Puzzle is hiring. Open roles at puzzle.ioP.S.S If you’re building in finance, accounting, or AI. Let’s connect!

Experience

1. Podcast Host - Tech Finance by A16z Studios

   Turpentine

   Apr 2024 — Present

   A podcast where I talk to Office of the CFO founders, accountants and finance leaders at the best tech companies about what it takes to architect success in the accounting and finance space.Listen and subscribe here:Spotify:https://open.spotify.com/show/5BflNhFxxLjqT2RA47352GApple: https://podcasts.apple.com/us/podcast/turpentine-finance-with-sasha-orloff-startup-finance/id17••••••64Youtube:

Education

• University of Cambridge

  Semester Abroad (Pembroke College), Economics

  1998 — 1998

• UC San Diego

  BS, Applied Math and Economics, Double Minor in Behavioral and Cognitive Psychology

  1995 — 1999

• Georgetown University McDonough School of Business

  MBA, Finance

  2004 — 2006

• Y Combinator

  W'12 Batch

• Harvard Business School Online

  Continuing Education, (1) Corporate Finance and Valuations

  2019 — 2019

• Stanford Continuing Studies

  Continuing Education, (1) Effective Board Governance (2) People Analytics

  2019 — 2019

• EHU

  Semester Abroad, European Art History & Culture

  1998 — 1998

Skills

• Rock Climbing
• Forecasting
• Compliance
• Venture Capital
• Microfinance
• Credit
• Soccer
• Analytics
• Risk Management
• Segmentation
• Customer Acquisition
• Baking