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John Sillings

Founder at Mini Exhibitions (YC W20)

John Sillings is a professional with a background in product and growth. He co-founded Mini Exhibitions and Art in Res with John Friel and has an extensive educational history, including studies at Y Combinator, New York University, and Hamilton College. John has held various roles in different organizations, such as Head of Growth at Checksum.ai, Growth Lead at super{set}, Director of Product Management at Stanza, and multiple positions in equity analysis and portfolio management. His experience ranges from financial institutions to educational settings, showcasing a diverse skill set.

Highlights

Sep 6 · linkedin

Last Friday was my last day at super{set} and Checksum.ai.

First: I’m extremely grateful for my time at (what Supersetians endearingly refer to as) “the hive.” It was a great experience. Fun and curious colleagues, caring and trusting managers, and a high autonomy, fast, slightly chaotic, very collaborative culture.

And obviously, I’m incredibly excited about my new role, and I’m excited to share a lot more about it in subsequent posts. But first, some reflections on career-related stuff:

The pace of learning as a founder is incredible. Part of it is the sheer scope because you’re, in some real sense, responsible for everything. And part of it is the desperation to succeed and all that comes with it: longer hours, heightened focus, speed and resourcefulness.

After I decided to take a full-time job – the first time I did that in about 5 years of running my own startups – I was pretty worried about getting bored or feeling unchallenged. But I was really intentional about my next moves, and it honestly went great.

The growth role at a startup has a lot of the same founder dynamics. The scope is narrower, but still huge. The success & desperation dynamics are similar, too: it’s one of the less forgiving jobs (basically perform or die), and the potential upside is basically uncapped, and very much in your control.

Team and culture was, and continues to be, a non-negotiable for me. I think this is the single biggest factor that basically permeates into everything else: how much fun you have, how much you learn, how motivated you feel, etc. I loved my super{set} team and I’m totally excited about my new team.

Startup studios have many interesting features, especially as an employer. There is 100% a structural advantage when it comes to learning. Startups were founded, shut down, acquired, etc. – but on average, we had 12 companies running at any given time. Different phases, sales motions, industries. It really made the commonalities stark – and the pace of experimentation was ridiculous because as soon as something worked at startup 1, I could try it at startup 2 through N.

Working with founders is also a huge, huge plus for me. Rather than feel like some weirdo egghead for being obsessed with learning new stuff, or overly enthusiastic about some esoteric growth hack, or just overly ambitious, I feel appreciated and seen. I figured this would be the case, and it totally is.

When it comes to my new role, I really couldn’t be more fired up about it. These were major considerations in making the move over to my new company. And I hope these reflections might be helpful to some others out there, especially other founders and ex-founders, who are thinking about their next thing.

And one more big thank you to super{set} – it was an awesome ride.

Jun 12 · linkedin

Does Checksum ... actually work? 🤔

This is a pretty common objection we get. And we probably miss out on a lot of opportunities because people just assume it doesn't work.

It's also a fair objection, because yes – a lot of AI products just don't work well.

Quick context on the Checksum.ai product: we write and maintain E2E tests for web apps, using AI.

I am THE ONLY non-technical person on the Checksum team. (And I'm more technical than your average non-technical person.) Literally everyone on the team, other than me, is obsessing over the product performance, 24/7.

Checksum isn't just a ChatGPT wrapper (like I suspect some competitors are) – it's actually a pretty sophisticated orchestra of vision, action, and large language models. This multi-model approach has led to huge performance gains.

Users can actually see that the thing works before they buy it – for 2 months, which is a pretty generous trial period, FOR FREE. This has been huge in dealing with this objection. But obviously, this approach only works if you have confidence in the product performance (which we obviously do).

So there you have it. Enjoy this photo of me traveling to SF...

Does Checksum ... actually work? 🤔

This is a pretty common objection we get. And we probably miss
John Sillings
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Kingston, New York, United States