Sasha Orloff

CEO

San Francisco, California, United States24 yrs 3 mos experience
Most Likely To SwitchAI Enabled

Key Highlights

  • Raised over $1B in venture capital.
  • Pioneered AI integration in accounting.
  • Hosted Tech Finance Podcast with industry leaders.
Stackforce AI infers this person is a Fintech leader specializing in AI-driven accounting solutions.

Contact

Skills

Core Skills

AccountingAi IntegrationLendingStartup GrowthFinancial InnovationProduct ManagementFintech

Other Skills

AI accounting softwaregeneral ledgerfinancial intelligenceautomationcredit card designcapital raisingteam buildingmobile lendingfinancial educationregulatory compliancemonetization strategiesmobile app development

About

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!

Experience

Turpentine

Podcast Host - Tech Finance by A16Z Studios

Apr 2024Present · 1 yr 11 mos · Remote

  • A podcast whet 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/5BflNhFxxLjqT2RA47352G
  • Apple:
  • https://podcasts.apple.com/us/podcast/turpentine-finance-with-sasha-orloff-startup-finance/id1704418764
  • Youtube:
  • https://www.youtube.com/@turpentinefinance

Puzzle

Cofounder & CEO

Sep 2019Present · 6 yrs 6 mos · San Francisco Bay Area

  • Puzzle is AI accounting software loved by startup and small business accounting firms. We’ve taken the best of QuickBooks, OpenAI, and Stripe, and rebuilt the general ledger from the ground up architected for provable accuracy. Given modern APIs and AI, it turns out to be quicker than legacy accounting softwares as well. Higher accuracy and more efficient.
  • Our mission is to make accounting and finance a competitive advantage for every company, not just the large companies who can afford experienced finance teams. We turn accounting from static, outdated reports into a real-time system of financial intelligence.
  • Our key insight: a financial data platform and general ledger are far more powerful together than apart. This unlocks new capabilities for founders and finance teams, with built-in collaboration, automation, design, and AI — everything you’d expect from modern software.
  • The name Puzzle came from a CFO who called us “the missing piece of a modern finance stack.”
  • We’re backed by world-class investors including General Catalyst, Fog Ventures (a syndicate of 125+ CFOs, CPAs, and operators), XYZ, S32, Felicis, Village Global, Kapor Capital, a YC alumni syndicate, and many other amazing angels and advisors.
AI accounting softwaregeneral ledgerfinancial intelligenceautomationAccountingAI Integration

Revolut

Non Executive Director

Sep 2019Jan 2022 · 2 yrs 4 mos

  • Revolut is the largest global fintech superapp and one of the largest private fintech companies in the world. Revolut helps people get more out of their money in over 35 countries with millions of users. I was a Non-Executive Board Director for Revolut's US business.

Limited partner

Investor

Jan 2019Jan 2022 · 3 yrs

  • Became a limited partner in multiple venture funds, supporting and evaluating early-stage startups. Focus areas included payments, lending, insurance, accounting and broader fintech, investing, and AI.

Lendup

2 roles

Board Member & Advisor

Dec 2018Oct 2019 · 10 mos

  • Following the spin-out as an independent company, I remained involved for a short transition period as a board member and advisor to support the handoff to the new leadership team and new ownership structure. My role concluded after the transition, and I was no longer involved with the company.

Cofounder & CEO

Jan 2012Dec 2018 · 6 yrs 11 mos

  • What was LendUp?
  • LendUp was a mission-driven lending company created to challenge predatory payday loans. We launched the LendUp Ladder to help turn short-term loans from a debt trap into a safe opportunity to build credit. Over its life, LendUp issued more than 6 million loans and saved customers hundreds of millions of dollars.
  • Technology + Education + Lending = Better Together
  • LendUp was the first U.S. company to offer mobile lending with instant decisions, instant funding, and the first to embed financial education directly into the product. We worked with federal regulators to close predatory loopholes via SBREFA, became the first short-term lender to report to credit bureaus, partnered with the Aspen Institute on nationwide financial education, and saved customers millions in predatory fees.
  • LendUp named one of the "World's Most Innovative Companies"
  • Backed by leading investors such as Y-Combinator, Google Ventures, QED Investors, Startfund, Kleiner Perkins, Thomvest Ventures, Kapor Capital, Bronze Investments, Data Collective, Susa Ventures, Radicle Impact, Victory Park Capital and a bunch of amazing angels and entrepreneurs. We were named one of the "World's Most Innovative Companies" in 2018 by Fast Company.
  • The Mission Lane Spin-Off & Stepping Down From LendUp
  • In 2018 we spun off the credit card subsidiary to a consortium of investors, with new management using the proceeds to further LendUp’s mission (and balance sheet!) as an independent company. At that time I stepped down as CEO and helped support the transition to a new CEO and new leadership.
  • Several years later, in 2022, LendUp unfortunately wound down its operations.

Mission lane

2 roles

Advisor

Dec 2018Oct 2019 · 10 mos

  • Following the spin-out as an independent company, I remained involved for a transition period as an advisor to support the handoff to the new leadership team and new ownership structure. My role concluded after the transition, and I am no longer involved in the company, but I’m proud of the foundational work that enabled Mission Lane’s growth and excited about the positive impact they continue to deliver.

Cofounder & CEO

Aug 2014Dec 2018 · 4 yrs 4 mos

  • We built what became one of the first venture-backed credit cards and the first card intentionally designed to help consumers understand, build, and improve their credit health. Our products embedded education, transparent pricing, and behavior-based incentives that rewarded real financial progress.
  • As founder and CEO of LendUp Card, I raised the capital, incorporated the entity, secured multiple bank partnerships, led the operations and capital-raising strategy, designed the first credit and fraud policy and oversaw the launch to thousands of customers. We recruited an exceptional team of operators, engineers, designers, credit experts, and risk leaders to scale the business.
  • The First Transaction
  • The first transaction processed was a flower delivery to my wife. It worked!
  • Product & Technology Innovations
  • During this period, we built two of the highest-rated credit cards in the category (the L Card and Arrow Card). We also introduced several first-of-their-kind capabilities to the subprime/near-prime card space, including one of the earliest mobile controls that allowed a customer to instantly turn their card on or off.
  • Spin-Out to an Independent Company
  • The business grew into what would now become Mission Lane (a much better name as well!). In 2018, the credit card business (originally LendUp Card) was spun out as a standalone company through an asset sale to a new investor group that included QED, Invus Opportunities, LL Funds, Oaktree, and Goldman Sachs. A new executive team stepped in to operate and scale the company.
  • Mission Lane went on to surpass 2 million customers by February 2023.
  • I am no longer involved in the company, but I’m proud of the foundational work that enabled Mission Lane’s growth and excited about the positive impact they continue to deliver.
credit card designcapital raisingteam buildingLendingStartup Growth

The aspen institute

Advisory Group Member

Jan 2017Jan 2019 · 2 yrs

  • I was invited to be part of the advisory group at EPIC, part of The Aspen Institute.
  • EPIC is a first-of-its-kind initiative in the field of consumer finance, designed to harness the knowledge of a wide cross-section of experts working in applied, academic, government, and industry settings toward the goal of illuminating and solving critical dimensions of household financial insecurity.
  • As part of Aspen’s Financial Security Program (FSP), EPIC deeply explores one issue at a time, focusing on challenges that are critical to Americans’ financial security but under-recognized or poorly understood. EPIC uses an interdisciplinary approach designed to uncover new, unconventional ways of understanding the issue and build consensus among decisionmakers and influencers representing a wide variety of sectors and industries.
  • The ultimate goal of EPIC is to generate deeply informed analyses and build diverse expert networks that help stakeholders (1) understand and prioritize critical financial security issues, and (2) forge consensus and broad support to implement solutions that can improve the financial lives of millions of people. Our first issue was income volatility, followed by the current initiative on consumer debt, and most recently focused area on housing stability and affordability.
mobile lendingfinancial educationregulatory complianceLendingFinancial Innovation

Transunion

Advisory Board Member (Fintech)

Jan 2014Dec 2017 · 3 yrs 11 mos

Citi

2 roles

Senior Vice President, Citi Ventures

Promoted

Oct 2010Feb 2012 · 1 yr 4 mos · Palo Alto, CA

  • Invest money, foster financial innovation, and facilitate disruption in financial services

Vice President, Consumer

Jul 2006Apr 2010 · 3 yrs 9 mos · New York, New York

  • Post-MBA Leadership Development Program that consisted of 4 rotations:
  • 1. Risk Management: Credit policy, score validation, risk forecasting.
  • 2. Finance: P&L Forecasting, marketing optimization, contract negotiation.
  • 3. Acquisition Analytics: Marketing campaigns, multi-variate testing, campaign optimization.
  • 4. Customer Insights: Analytics and concept testing in the consumer division.
monetization strategiesmobile app developmentProduct ManagementFintech

Check inc. (now mint bills)

Revenue Consultant

Apr 2010Oct 2010 · 6 mos · San Francisco Bay Area

  • Check was acquired by Intuit for $360M in 2016.
  • I helped the team devise monetization strategies for fastest growing mobile app for personal financial management, including bill payment, which is now known as Mint Bills.

The world bank

Global Technology Microfinance Analyst

May 2005Aug 2005 · 3 mos · Washington D.C. Metro Area

  • Microfinance Analyst at the Consultative Group to Assist the Poor, specializing in technological innovation in global financial services across credit, savings, insurance, distribution, and identity.

Grameen foundation

Volunteer (Microfinance Technology Focus)

Jan 2002May 2005 · 3 yrs 4 mos · La Ceiba, Honduras and Chiapas, Mexico

  • International volunteer role similar to the Peace Corp. Following the pioneering vision of Muhammad Yunus and his Nobel Peace Prize, I worked in Honduras, Mexico and Washington DC focused on product and analytics for what became an open source software solution (MIFOS) and licensed software (M2) to help microfinance institutions manage and expand operations, reporting and control in high growth potential microfinance operations in Latin America. Inspiring mission driven non-profit.
  • Fundacion Adelante (La Ceiba, Honduras)
  • Alsol (Chiapas, Mexico)
  • Grameen Foundation (Washington DC)

Ingenio

Analyst

Feb 2000Oct 2001 · 1 yr 8 mos · San Francisco Bay Area

  • Ingenio and was acquired by AT&T/Yellowpages in 2007.
  • I held two positions. The first was a Trust & Safety Analyst writing business risk & intelligence queries and transaction analysis to better manage fraud and our business. The second was an Online Marketing Associate developing verticals and partnerships to grow our business.

Education

Harvard Business School Online

Continuing Education — (1) Corporate Finance and Valuations

Jan 2019Jan 2019

Stanford Continuing Studies

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

Jan 2019Jan 2019

Y Combinator

W'12 Batch

Jan 2011Mar 2011

Georgetown University McDonough School of Business

MBA — Finance

Jan 2004Jan 2006

EHU

Semester Abroad — European Art History & Culture

Jan 1998Jan 1998

University of Cambridge

Semester Abroad (Pembroke College) — Economics

Jan 1998Jan 1998

UC San Diego

BS

Jan 1995Jan 1999

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