Sasha Orloff

Visionary
DISC Type : Ds

Podcast Host - Tech Finance by A16Z Studios at Turpentine

San Francisco, California, United States

Overview

Sasha Orloff is the Cofounder and CEO of Puzzle, an AI-powered accounting platform. A self-described "modeler, " he has over 20 years of experience using data and analytics to drive decisions. He has co-founded companies that have collectively raised over $1 billion in capital and pursued continuing education at Harvard and Stanford.

Outside of his entrepreneurial ventures, Sasha is a husband and a father to two children. He leverages his extensive experience in the tech and finance world to host the "Tech Finance" podcast in partnership with Andreessen Horowitz (A16Z), exploring insights from leaders in the CFO office.

In 2016, Sasha was named a Young Global Leader by the World Economic Forum.

Personality Overview

Risk Tolerant

Fast But Thoughtful

Goal-Oriented

They exhibit a rare combination of being result-oriented but patient at the same time.  They might take some time to make their mind up but once they do, they don't change it easily. They are very professional in their approach and can weigh multiple perspectives together.

Topics They Care About

AI in Accounting
He is building Puzzle as an AI-native accounting platform and frequently discusses how AI agents and automation are fundamentally changing the accounting industry for the better.
Startup Finance
His company, Puzzle, is built specifically for startups, and he hosts a podcast dedicated to the finance challenges and strategies for high-growth tech companies.
Data-Driven Decisions
Identifies as a "modeler" rather than a CPA, emphasizing his core belief that accurate, real-time financial data is essential for making sound business decisions.

Media Appearances

Sasha Orloff (Co‑founder & CEO of Puzzle). Featured in Spotify

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EP 4: Sasha Orloff, Co‑Founder & CEO at Puzzle. Featured in Slice of Finance

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Sasha Orloff, Co‑Founder & CEO of Puzzle on Accounting, …. Featured in YouTube

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Work History

4-2024
Podcast Host - Tech Finance by A16Z Studios at Turpentine
9-2019
Cofounder & CEO at Puzzle
9-2019 - 1-2022
Non Executive Director at Revolut
1-2019 - 1-2022
Investor at Limited Partner
12-2018 - 10-2019
Advisor at Mission Lane

Education

2019 - 2019
Continuing Education from Harvard Business School Online
2019 - 2019
Continuing Education from Stanford Continuing Studies

More Information

Social Presence :

Prographics :

Exp : 24 Location : San Francisco, California, United States Job Level : Leadership Designation : Podcast Host - Tech Finance by A16Z Studios at Turpentine
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Insights For Selling To Sasha

During A Call Or A Meeting

DO's

  • Let them know of potential risks but suggest mitigation methods alongside
  • Come across as a trustworthy professional and be respectful, they usually know their game
  • You can spend time on BANT (or other qualification methodology) but keep it to the point

DONT's

  • Don't take their patience for granted, avoid long-winding sermons
  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them
  • Don't get into pricing discussions early on, steer conversation towards proven results

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Sasha is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Sasha

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Sasha move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Sasha take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Sasha

Personality Compatibility


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