Jean Sini

Trailblazer
DISC Type : DI

Founder + Managing Partner at Irregular Expressions

New York, New York, United States

Overview

Jean Sini is the Founder and Managing Partner at Irregular Expressions, a venture fund investing in early-stage technical founders. A serial entrepreneur and former CTO at companies like Mint. com and Cadre, he has over two decades of experience building and scaling software companies. He holds Masters degrees from Télécom Paris and Pierre and Marie Curie University.

Outside of his professional life, Jean is described as having an adventurous spirit and is an avid kiteboarder and snowboarder. He has a long-standing passion for mentoring founders, which began in 2012, and he famously let the Canva co-founders live with him for months during their first seed round.

Unique fact: Jean was an early angel investor in the graphic design unicorn, Canva, and still serves as an advisor to the company.

Personality Overview

Friendly But Fast

Informal

Achievement-Oriented

They are more likely to be open to unproven but exciting technologies.  They will fight for you if they come to believe in you. They respond better to a combination of speed and relationship.

Topics They Care About

Early-Stage Investing
As the founder of Irregular Expressions, his focus is investing in pre-seed and seed stage companies, particularly those led by technical founders.
Infrastructure Software
His fund and personal investment thesis are centered on infrastructure, data engineering, AI, DevOps, security, and developer tooling.
AI in DevOps
His recent social media activity shows excitement for backing companies using AI to innovate in software architecture and DevOps automation.

Media Appearances

Jean has no verified media appearances

Work History

4-2018
Founder + Managing Partner at Irregular Expressions
Investor + Advisor at Canva
6-2016
Investor + Advisor at People.ai
3-2015
Investor at Antheia, Inc.
6-2025
Venture Partner at Partech

Education

1993 - 1996
MS from Télécom Paris
1995 - 1996
DEA from Pierre and Marie Curie University

More Information

Social Presence :

Prographics :

Exp : 10 Location : New York, New York, United States Job Level : Leadership Designation : Founder + Managing Partner at Irregular Expressions
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Insights For Selling To Jean

During A Call Or A Meeting

DO's

  • Build a trustworthy relationship while keeping the product center-stage
  • Ask them for a lunch or coffee once some rapport has been established
  • Address your competition clearly and confidently

DONT's

  • Don’t hesitate from asking questions or pushing them, but take a friendly approach
  • Don’t force involvement of other stakeholders unless it is critical
  • Don't make any commitments that you might not be able to fulfill

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jean is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Jean

  • If they are not convinced, they will say no albeit in a friendly manner.


Insights For Deal Planning

    How fast (or slow) will Jean move?

  • They can reach decisions quickly if they develop trust and confidence in the product.
  • Can Jean take some risk or not?

  • They can take risks if necessary.

You And Jean

Personality Compatibility


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