Sasha Orloff — CEO
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.io P.S.S If you’re building in finance, accounting, or AI. Let’s connect!
Stackforce AI infers this person is a Fintech leader specializing in AI-driven accounting solutions.
Location: San Francisco, California, United States
Experience: 24 yrs 3 mos
Skills
- Accounting
- Ai Integration
- Lending
- Startup Growth
- Financial Innovation
- Product Management
- Fintech
Career Highlights
- Raised over $1B in venture capital.
- Pioneered AI integration in accounting.
- Hosted Tech Finance Podcast with industry leaders.
Work Experience
Turpentine
Podcast Host - Tech Finance by A16Z Studios (1 yr 11 mos)
Puzzle
Cofounder & CEO (6 yrs 6 mos)
Revolut
Non Executive Director (2 yrs 4 mos)
Limited Partner
Investor (3 yrs)
LendUp
Board Member & Advisor (10 mos)
Cofounder & CEO (6 yrs 11 mos)
Mission Lane
Advisor (10 mos)
Cofounder & CEO (4 yrs 4 mos)
The Aspen Institute
Advisory Group Member (2 yrs)
TransUnion
Advisory Board Member (Fintech) (3 yrs 11 mos)
Citi
Senior Vice President, Citi Ventures (1 yr 4 mos)
Vice President, Consumer (3 yrs 9 mos)
Check Inc. (now Mint Bills)
Revenue Consultant (6 mos)
The World Bank
Global Technology Microfinance Analyst (3 mos)
Grameen Foundation
Volunteer (Microfinance Technology Focus) (3 yrs 4 mos)
Ingenio
Analyst (1 yr 8 mos)
Education
Continuing Education at Harvard Business School Online
Continuing Education at Stanford Continuing Studies
W'12 Batch at Y Combinator
MBA at Georgetown University McDonough School of Business
Semester Abroad at EHU
Semester Abroad (Pembroke College) at University of Cambridge
BS at UC San Diego