Founders: why we should meet, what I invest in, how I can help and founder feedback.
Founding Partner @ Irregular Expressions,
General Partner @ Partech.
Investor @ engineering infrastructure companies Treasure Data [exited], Bison Trails [exited], Medigate [exited], Datakin [exited], Memfault, Bubble, ProdPerfect, Okay, Shortcut, User Interviews, Educative, Alectio, Architect, Coherence, Product Science, Capability, @ fintech startups Nivelo, Trade Up, Atomic Invest, KickPay, Peachy, Nirvana, Anzen, Jeeves,Grove Financial, TeamPay, Amplify, and @ Canva, People.ai, FieldWire [exited], Firefly, MindKick [exited], Companion, Antheia, Constructor, 4D Sight.
Former VP, Engineering @ Mint, Ring, Porch.
Former CTO @ Cadre, One Kings Lane, Twelvefold.
Former Co-founder and CTO @ Fountain, Activeweave.
We should have met yesterday
Whether or not you’re currently fundraising, let’s get to know each other: companies are built over many years, and the investors you bring on to support you on that journey will likely be around through most of it.
So we both want to maximize the odds we’re a great and valuable match. Proxies help: what we’ve done, with whom, etc. But to truly find out, nothing beats getting meaningfully acquainted early, so we can actually find out whether our areas of interest and expertise are aligned and complementary and whether, together, we can grow the company faster and more successfully.
What I obsess over
I focus almost exclusively on business-to-developer companies, i.e. picks and shovels for engineering teams.
Engineering Infrastructure
Two dueling trends are making better developer tooling a core necessity: a chronic, global shortage of engineering talent, coupled with unrelenting appetite to further modernize every industry with software — leaving engineering teams scrambling to accomplish more with limited resources. The one place to turn to unlock productivity gains? Tools and infrastructure.
Business-to-developer tools and platforms transform the work experience of technology builders — whether software developers, machine learning engineers, designers, product managers or data scientists — and as such make them significantly more effective.
Think Dev Tools, Dev Ops, Security, Engineering and Data Infrastructure, Machine Learning, ML Ops platforms, etc.
How I get involved
Once an engineer, always an engineer: I think in systems, whether they apply to refining a recruiting process, a product organization, or a sales playbook.
I spent over twenty years working with amazing teams and co-founders, typically as CTO or VP of Engineering, at several startups: Activeweave, Twelve Fold, One Kings Lane, Fountain, Porch, Ring, Mint and Cadre.
Engineering and Product Teams
In addition to lots of scar tissue, that operating career left me with a continued passion to optimize the tools and practices leveraged by engineering teams so they deliver to their fullest potential.
It’s impossible to overestimate the importance of hiring and retaining astounding people when building the exceptional technology required to meet the needs of demanding markets. Naturally, equipping those teams with the best tools and practices out there is just as critical. So let’s invest early in
- Hiring and candidate experience,
- Team development,
- Organizational design,
- Engineering processes,
- Fine-tuning product-market fit,
- Avoiding scope creep,
- Tooling.
Growth
Building it doesn’t mean they will come, not without a repeatable playbook to acquire and retain customers. Whether it’s centered on product-led growth, top-down or bottom-up motions, an open-core approach, etc. your go-to-market strategy is ultimately what propels the company, or stalls it. Let’s dig in.
Partner ecosystem
The fundamental reason I specialize so narrowly on the business-to-developer category is to be a valuable partner.
I’m obsessed with nurturing a truly relevant ecosystem of investors, customers, partners and acquirers as you grow the company.
Specifically and concretely, in 2018 I started running a syndicate of operating engineering leaders that, in 2022, we morphed into a fund, Irregular Expressions, focused exclusively on backing seed-stage business-to-developer startups.
Over 80 CTOs and VPs of Engineering at high-growth technology companies constitute the fund’s core advisors and investors.
Crucially, this group has proven an incredible resource to founders as an on-going sounding board: the teams those engineering leaders run typically represent the ideal customer profile of any business-to-developer startup.
Founder Feedback
I’ve been extremely fortunate to back incredible founders. Here are a few words from them about our work together.
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.
Melanie Perkins @ Canva
Jean is a super star. Believed in Canva before we even had a prototype and supported us through the fundraising and business building phases. Not to mention, he let us crash at his house for over a month (was supposed to be a couple of days) while we were trying to raise our seed round.
Cliff Obrecht @ Canva
Jean is one of the best technology leaders out there, hands down. I’m very lucky to have him as my investor and mentor.
Oleg Rogynskyy @ People.ai
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.
Jennifer Prendki @ Alectio
Working with Jean and the Partech team throughout the investment process was a highly professional experience. They came prepared with the right level of industry and competitive knowledge to advance the process. The process was also well balanced between the commercial aspects of our company and the technological / product aspects. Finally, they were friendly and easy to work with which helped accelerate the process and create a positive experience. Following the investment, Jean and team have always been attentive to our needs and available to assist within our timeframe. They have provided warm introductions to the right people, professional guidance and insights when requested, and a lending an ear to help address pressing issues. They have been a great investment partner.
Jonathan Langer @ Medigate
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.
Basel Fakhoury @ User Interviews
It’s been a tremendous pleasure working with Jean over the past year and a half. From our very first breakfast in San Francisco, Jean immediately understood the potential of our company and brought his experience as a founder and engineering leader to bear. The team at Partech moved fast and was great to work with throughout the financing process. Since then, Jean has worked alongside us to close hires, find customers, and wrestle with difficult strategic questions. I’m thrilled to have him on my board, and look forward to a long journey together.
François Baldassari @ Memfault
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.
Eli Polanco @ Nivelo
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.
David Dindi @ Atomic Invest
Jean Sini: backing early-stage founders. 