Engineer leaders investing in Infrastructure, Data Engineering, AI, DevOps, Security, Observability and Developer Productivity startups, at the pre-seed and seed stages

Irregular Expressions (IrregEx for short), backed by a group of seasoned software engineering and product leaders, invests in and advises early stage infrastructure, data,  and machine learning startups.

We’ve spent many cumulative decades bringing high-growth software products to market, and are focused on helping founders scale their own teams, products and businesses faster, leveraging both our know-how and our network.

Having co-founded, built and scaled hundreds of companies, primarily in the San Francisco and New York ecosystems, we love working closely with the founders and teams we back, and thinking together through thorny challenges on the product, engineering, and business fronts alike.

TEAM Spotlight

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Vlad Rachev

Software Engineer @NextDoor, Principal @Irregular Expressions, Software Engineer - Developer Productivity @MongoDB

Alexandre Attia

Co-Founder & CTO @AZmed

Hrishi Dixit

Founder/Principal @Gordian Labs, Founding CTO @Yieldstreet, Founding CTO @LearnVest

Cyril Deremble

Quantitative Portfolio Manager @Point 72 Cubist Systematic Strategies, Quantitative Investigator Intern @AMF France, Co-Head of Directional Strategies @Capital Fund Management

Ben Roberts

Director of Data @Remote, Director of Data & Analytics @Brooklyn Data Co., Head of Data & Analytics @Nested

Achin Batra

VP of Engineering @Thirty Madison, VP of Engineering @Flatiron Health, Sr. Software Engineer @Bazaarvoice, Software Engineer @Goldman Sachs

Benjamin Fabre

Co-Founder & CEO (former CTO) @DataDome, COO @Linkfluence, Co-Founder & CTO @TrendyBuzz

Julie Hubschman

Head of Developer APIs @FIS, Senior Product Manager @DriveWealth, Developer Relations Lead @Gusto, Engineer @Pinterest, @Micrsoft

Kellan Elliott-McCrea

Head of Engineering Frame.io @Adobe, VP of Engineering @Dropbox, SVP of Engineering @Blink Health, CTO @Etsy

Katelyn Lesse

Head of API Engineering @ Anthropic, Engineering Leader @Stripe, Senior Director of Engineering @Betterment

Laura Florescu

Founder @Generative Alpha, AI Researcher @MosaicML, Principal Engineer @SambaNova Systems, Software Engineer @Groq

Junaid Ahmed

VP of Engineering @Datadog, Director of Engineering @Apple, General Manager @Microsoft

James Turnbull

VP of Product & Engineering @Smartrr, SVP of Engineering @Sotheby's, VP of Engineering @Timber.io,VP of Engineering @Glitch

Taylor Leese

Senior Director of Core Infrastructure Primitives & Storage @LinkedIn, Senior Director of Platform Services @Twitter

James Psota

Co-Founder & CTO @Panjiva (acquired S&P Global)

Michele Catasta

VP of AI @Replit, Head of Applied Research @Google Labs, Head of Applied Research @X, the moonshot factory

Pablo Mendes

Co-Founder & CEO @Objective, Senior Researcher & Engineering Manager @Apple

Jonah Cohen

VP of Analytics & Business Operations @MongoDB, Strategy Director @PepsiCo, Management Consulting @Various Firms

Fazal Yameen

Advisor @Wombat Invest, VP of Product @Stash, VP of Product @GPShopper (Synchrony), Head of Product @comiXology (Amazon)

Sam Moore

VP of Architecture @Betterment

Renaud Visage

Founding Partner @Slate Venture Capital, Co-Founder & CTO @Eventbrite, Venture Partner @Point Nine, Venture Partner @Index Ventures

Zachary Ozer

VP of Engineering @Column Tax, VP of Engineering @Shortcut, Director of Engineering @Compass, Tech lead @JW Player

Matthew Drooker

CTO @SoundCloud, SVP of Platform Technology, Products & Operations @Turner

Nick Rockwell

EVP of Engineering & Infrastructure @Fastly, CTO @TheNewYorkTimes, Mentor @Techstars

Jurica Cerovec

Co-Founder & CTO @Microblink, Software Engineering @Racuni.hr

Zach Abrams

Co-Founder @Bridge, CPO @Brex, Director Product Management @Coinbase, @Remind, Lead Product Manager @Square

Yony Feng

Co-Founder & CTO @Ernesta, Co-Founder & CTO @Peloton, Software Engineer @Skype& @Cisco

Varun Srinivasan

Co-Founder @Farcaster, Senior Director of Platform @Coinbase, Product Management @Microsoft

Theresa Vu

CTO @Praxis Labs, SVP of Engineering @Xandr (previously AppNexus)

Tejpaul Bhatia

CRO @Axiom Space, Executive Engagement & Thought Leadership @Google, COO @Explain Everything

Sylvia Isler

Senior VP, Head of Engineering @Better Life Partners, Senior Engineering Manager @Google, VP of Engineering @Cityblock Health, SVP of Engineering @Turbonomic

Swaroop Butala

Director of Engineering @Box, Co-Founder @Stealth

Supreet Oberoi

SVP of Engineering @BriteCore, SVP of Engineering @Demandbase, VP IoT & Big Data Applications @Oracle

Steven Kuyan

Co-Founder & CEO @Luro Health, Co-Founder & Co-CEO @Culina Health, Director @NYU Center for Responsible AI, Managing Director @NYU Tandon Future Labs

Sheba Rasson

Global Product Lead @Google, CX Strategy Manager @The New York Times

Serkan Kutan

CTO @Zelis, Co-Founder, Fractional CTO/CPO @WorldClass Health, CTO/Advisor @Kutan Technology Partners, CTO @Amwell, CTO @Haven, CTO @Zocdoc

Scott Breitenother

Founder @Brooklyn Data Co., Co-Founder @LocallyOptimistic, VP Data & Analytics @Casper, Consultant @L.E.K

Samuel Rozenberg

SVP of Engineering @Hinge, CPO & CTO @Artsy, Engineering Manager @Instagram, Tribe Lead @Spotify, Quant Trader @Nomura

Sameer Jain

CIO @Nomura, Co-Founder & CTO @USREM, CTO @Barclays

Romain David

E-commerce Entrepreneur, Product @Uber

Robyn Peterson

SVP of Advertising Technology & Technical Advisor @Warner Bros. Discovery, CTO @CNN, CTO @Mashable

Rachana Kumar

CTO @Etsy

Peter Bell

CTO @Engineer Access, Founder & CTO @CTO Connection, Senior Director @The Flatiron School, SVP of Engineering @General Assembly

Ori Schnaps

Vice President of Engineering, Core Product @Reddit, Director of Engineering @Facebook, VP of Engineering @Zocdoc, Global Head of Technology @Thomson Reuters

Oliver Plattner

Chief Product & Technology Officer @Alto, SVP of Engineering @Skillsoft, CTO @Codeacademy, Head of People Engineering @Uber, Director of Engineering @Anaplan

Nate Wiger

CTO @Pipe, VP of Product Management @Intuit, Founder @Amazon San Diego Tech Hub, Head of Specialist Solutions Architects @AWS, Director of Engineering @Playstation

Mircea Pasoi

Co-Founder @Istari Co., Engineering Manager @Clubhouse, Engineering Manager @Novi Financial, Head of Identity Engineering @Coinbase, Senior Engineering Manager @Twitter, Founder of 2 companies that were sold to Twitter & Coinbase

Mike Reust

President @Betterment

Mike Boufford

Co-Founder & CEO @Otti, CTO @Greenhouse, Software Developer @Thomson Reuters, Independent Consultant @LendingTree

Michael Coyne

Software Architect @Huntress, CTO @Publicist, Strategic Technology Advisor @ThriveFantasy, VP of Engineering @Knotch

Matt Driscoll

Group Product Manager @Google, Director of Product @Cadre, Lead Product Manager @Square

Maria Belousova

CDO @Indigo, CTO @Grubhub, VP Technology @Bluefly, Founder and CEO @Davai.com, Lead Software Development Engineer @Microsoft

Marcus Frödin

VP Engineering @Spotify

Marc Meyer

Executive Coach and Advisor, Trustee and Advisor Council Chair @UC Berkeley SkyDeck, Founder @Tibco

Marc Brown

CTO @Caire, Director of Engineering @Ro, Co-Founder & CTO @Lever Health

Mackenzie Kosut

Startup Leader @Microsoft, earlier @AWS, @Oscar Health

Liz Maida

Co-Founder & CEO @Fathom, Co-Founder & CEO @Uplevel Security, Senior Director Product Development @Akamai Technologies

Leonid Igolnik

EVP of Engineering @Clari, General Partner @IA Seed Ventures

Laurent Paris

SVP of Engineering @Datadog, SVP of R&D @Astronomer, Co-Founder & CEO @Datakin, CTO @WeWork

Kurt Schrader

Co-Founder & CEO @Shortcut, Co-Founder @CTO School

Kathleen Yanolatos

Head of Engineering @Exos, Senior Director of Product Engineering @WW, SVP of Product & Engineering @Aaptiv

Julie Sommerville

Senior Director of Engineering @1Password, VP of Engineering @ChartHop, VP of Engineering @Capsule, Director of Engineering @Blue Apron

Joel Witten

Data Science @Meta, Head of Data @Rec Room, Data Science Manager @Facebook, Head of Data Engineering & Analytics @Venmo, Data Engineering @SquareSpace

Jay Signorello

VP of Engineering @Zillow Group

James Boehmer

CTO & Co-Founder @Stealth, Senior Manager of Engineering @Etsy, VP of Engineering @Altana, VP Content Engineering @Disney Media

Irina Krechmer

CTO @Blue Apron, VP Engineering @XO Group, Executive Director of Engineering @Amplify

Ilia Papas

CEO & Co-Founder @Band, Founder & Former CTO @Blue Apron

Ilan Man

SVP, Data Strat & Insights @Brooklyn Data, Head of Data Science @Lokavant, Head of Data @TrialSpark & @Paperless Post, Data Science @Squarespace

Greg Ratner

Senior Director of Software Engineering @Slack, Co-Founder & CTO @Troops

Gil Shklarski

CTO @Thirty Madison, General Partner @Operator Partners, CTO @Flatiron Health, Startup Mentor @First Round Capital, Software Engineer @Facebook, @Microsoft, R&D manager @IDF

Geoff Calkins

Chief Product and Strategy Officer @Canopy, SVP Product Management & Operations @Flatiron Health, Consultant @Bain & Company

Elijah Meerson

CTO @Paradigm, CTO @Orchard, VP Engineering @Flatiron Health, Engineering Manager @AppNexus

Doug Bemis

Co-Founder @Syntracts, Head of Engineering @Redesign Health, CTO @Optoro, Co-Founder & CTO @Uber

David Andre

Chief Science Officer @X, Founder and CEO @Cerebellum Capital

Danny Morrow

CTO @Extend, Technical Team Lead @Elephant

Dan Preston

Board Member @Dave, SVP of Strategic Initiatives @Lemonade, CEO @Metromile, Software Engineer @Google

Chris Crane

Co-Founder & CPO @fiveonefour,  Head of Product @Datalogue (acquired by Nike), GM & VP Product @Sysdig, Associate @Bain Capital Ventures

Carter Perez

CEO @SaaSy Sales Leadership, Co-Founder & CEO @Revenue Chemists, Head Coach @ScaleWise

Carlos Aguilar

Founder & CEO @Hashboard, VP of Data Insights Engineering @Flatiron Health, Systems Engineer @Amazon Robotics

Camille Fournier

Head of Engineering & Architecture @JPMorgan Chase, Head of Platform Engineering @Two Sigma, CTO @Rent The Runway

Bryan Mahoney

Co-Founder and CEO @Chord, CTO @Glossier, Co-Founder @Dynamo

Brian Murphy

CTO @SeatGeek, CTO @Tumblr, VP Engineering @The New York Times

Ben Birnbaum

Co-Founder, President, and CTO @Inductive Bio, Senior Engineering Director @Flatiron Health, Senior Software Engineer @Google

Ashley Miller

VP of Application Infrastucture @Datadog, Senior Software Engineering Manager @BuzzFeed & @Birchbox

Arun Nagarajan

CPO & CTO @Evolve, Co-Founder & CTO @BigSpring, Director Engineering @Uber, VP Engineering @Twenty, Tech Lead, Developer Platform @Google

Ariana Poursartip

Product Lead @Bridge, Product Lead @Shopify, VP of Product @Petal

Antoine Boulanger

Engineering Leader @Stripe, Co-Founder & CEO @Okay, Senior Director of Engineering @Box, Engineer @Google

Anthony Johnson

CTO and Co-Founder @Lighty AI, CTO @Swiftline, CTO @Thrasio, CTO @Giphy

Andrey Akselrod

Co-Founder @Stealth, CTO @People.ai, Founder & CTO @Smartling

Andrew Hogue

Engineering Director @Google, VP Engineering @Blue Apron, SVP Engineering @Foursquare

Andrew Bunner

Senior Staff Software Engineer @Google, Director of Engineering @Six Apart

Ali Heron

Managing Director @GrowthCurve Capital, CTO @Petal, SVP of Engineering @Two Sigma, EIR @NYU

Alexis Lê-Quôc

Co-Founder & CTO @Datadog, Director of Live Operations @Wireless Generation (now Amplify)

Alexandre Winter

Co-Founder & CEO @Norbert Health, Founder & CEO @LTU Technologies, Founder & CEO @Placemeter

Alex Ingram

Co-Founder @Zest, Co-Founder @Sunlight Health, Director of Product Management @Flatiron Health

Alan Warren

CTO @The Commons Project, CTO @ Oscar Insurance, VP Engineering @Google

Adam Perelman

Product Engineering @OpenAI, CTO @Affinity, Software Engineering @Facebook & @Google

Adam Bildersee

Global Head of Engineering @ Moon Creative Lab, Founder @ Axle Medical, Tech Lead & Manager @ Verily Life Sciences

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Meet the team

Portfolio Highlights

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4D Sight

4D Sight creates virtual billboards for e-sports leagues. Audiences see ads, gamers do not. As such, the company acts as a stream monetization platform for e-sports and streamers. The company’s technology inserts ads into the game environment in real-time but doesn’t require any integration with the game engine, and doesn’t interfere with gamers’ experience either.

Bubble

Bubble is a no-code software development platform that empowers people without programming skills to design, develop, and launch their own applications, tech products, or tools for solving their business problems.

People.ai

People.ai delivers the industry’s leading ROI platform. It transforms business activity data into recommendations that increase the impact of Sales, Marketing, and Operations.

Canva

Canva is a simple-to-use online design and publishing platform that allows everyone to create professional quality designs.

Treasure Data

Treasure Data is a global leader in Customer Data Platforms (CDP) and enterprise data management. Providing the ability to aggregate and translate massive volumes of scattered and siloed data.

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View Portfolio

Latest

what founders say about us

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If I had one thing to say about Jean, it would be that everything that he does is purposeful and meaningful! Few investors put as much time and effort into understanding our technology, our business model and our challenges; but once Jean decided to make the jump, he was all in and has been one of the most precious allies to Alectio and to me so far. If I need an introduction, he will just make it happen. Jean is one of those people you feel better having by your side, who are there when you need them - whether it's because you need strategic advice, or just because you need a listening ear.
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Jennifer Prendki
,  
Alectio
Jean and Irregular Expressions have been great partners and investors for User Interviews. Even before we were fundraising, Jean was able to give helpful intros and advice on scaling. His experience as an operator allowed him to understand and get up to speed on the market incredibly quickly. Once we began to fundraise they moved fast and had a very smooth, founder friendly process. Everyone in Irregular Expressions is a successful operator, so the questions and conversations felt more like a mentor session than a pitch. Post-investment everyone has been available and engaged whenever I had a request. I’ve done working sessions on GTM strategy and product philosophy with people from Irregular Expressions network. I also have very helpful quarterly meetings with Jean to go over the business. I’m very grateful I’ve had the opportunity to work with Irregular Expressions and look forward to scaling User Interviews with them as partners.
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Basel Fakhoury
,  
User Interviews
I found Jean to be very thoughtful and structured in the way that he approached his investment decision. He takes the time to make sure that he understands the nuance of your business and to offer valuable perspectives drawn from his past experiences. He is very much a “System 2” thinker, which I greatly appreciate. Post-investment, he has been very proactive in finding ways to support our initiatives -- from making valuable intros to meeting with candidates on our behalf. He's been a great partner to Atomic.
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David Dindi
,  
Atomic Invest
Jean was incredibly helpful brokering introductions and investments from stellar engineering experts who could be force multipliers to our business. These experts have been tremendously helpful in my recruiting process as I grow my company post Seed investments. Jean has also made himself available post-investment for any help needed. It's been a great relationship to us and would recommend to founders with a strong focus on capital that is strategic.
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Eli Polanco
,  
Nivelo
Jean is one of the best technology leaders out there, hands down. I'm very lucky to have him as my investor and mentor.
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Oleg Rogynskyy
,  
People.ai
Jean was one of the first investors we ever pitched and shared the vision for Canva with, back in 2012 when he was on a trip to our home town in Perth, Western Australia. Jean was incredibly supportive back then, and his support has continued over many years - letting us crash at his apartment for *months* as we pitched for our first round of funding, he listened to our unpolished pitch many times, he introduced us to great people in his network, gave great advice and lent a friendly ear too many times to count. We're really lucky to have met Jean along our path.
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Melanie Perkins
,  
Canva
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