The Download: Hayley Sullivan, Founder and CEO of The Styled by Collective

Before launching The Styled by Collective a tech-forward personal styling company that’s quietly redefining how women dress – former Palantir employee Hayley Sullivan spent ten years working in cybersecurity.

It’s the kind of unexpected career pivot that makes perfect sense in retrospect: precision, systems thinking, and a deep understanding of digital ecosystems are all baked into her approach to style.

Now at the helm of a growing business, Hayley’s less about trend-chasing and more about designing tools that strip away the overwhelm. Her team is currently integrating a digital wardrobe tool that uses AI to surface the right pieces at the right time – and filter out the rest.

But don’t let the polished exterior fool you. Hayley’s still the kind of founder who lives in the Notes app, swears by a good dongle, and believes the best tech is the kind you don’t even notice working. “Systems should be designed for ease of use, not to show off how smart they are. If a tool takes too much effort to maintain, it becomes background noise,” says Hayley.

From her Leica Q2 to her Kindle, she’s mastered the art of balancing sleek software with sophistication. Scroll on as Hayley shares the tools, gadgets, and software shaping her streamlined digital life…

The Download with Hayley Sullivan:

My top three gadgets are…

My iPhone is both a mobile command centre and a creative diary. I use it to capture everything from client fittings to moments of inspiration. My Leica Q2 is essential for travel. It brings a cinematic quality and a sense of spontaneity that a phone camera just cannot match. I also rely on my Kindle, which is always within reach when I need to reset. And while it may not be glamorous, I swear by the dongle that connects my Leica SD card to my phone. My friends joke that I live by the phrase “always be dongling.”

My favourite softwares platforms are…

ChatGPT, Reclaim AI, and Notion. AI helps me brainstorm, structure strategy, and reshape long-form content into usable outputs. Slack keeps our team in sync across time zones. We also built proprietary software that manages every detail of the inventory lifecycle across our vendor network and then visualises that data for each client inside their digital wardrobe. We plan to release it publicly as an app next year.

My top tech tip is to…

Keep it simple. Systems should be designed for ease of use, not to show off how smart they are. If a tool takes too much effort to maintain, it becomes background noise. I build our workflows the same way we build wardrobes. They are intuitive, functional, and beautifully streamlined. And while it may be basic, I live in the Notes app. It allows instant collaboration with anyone who uses an iPhone, without needing logins or licenses.

I stay up to date with tech by…

Habit and instinct. I spent ten years in enterprise cybersecurity before founding The Styled by Collective, so I naturally pay attention to how systems evolve. I read The Wall Street Journal and scroll TikTok and Instagram just like everyone else. Most importantly, I learn through conversation with other founders, stylists, and engineers who are shaping what is next.

I am excited about AI…

But only when it enhances something human. What excites me is its ability to support high-touch personalisation. We are building tools that surface the right product at the right time and filter out what does not match a client’s identity. The idea is to transform the noise of online shopping into something calm, intentional, and beautifully edited. That said, style is emotional. Technology should assist, not replace, that human connection.

My favourite books and podcasts are…

The Tipping Point by Malcolm Gladwell helped shape my thinking around cultural momentum. A Short History of Nearly Everything by Bill Bryson offers the kind of perspective I need when things feel intense. And The Journal by The Wall Street Journal is my go-to podcast when I want fast, smart reporting without the fluff.

The fashion-tech innovation I love…

Alta by Jenny Wang is brilliant. It is reimagining the way fashion and media coexist, especially for those who value quality but move quickly.

My favourite beauty gadget right now is…

The Shani Darden red light mask. Huge price point, but worth it.

The Modems’ Byte-Sized Questions:

💻 iOS or Android? 

iOS always

🎧 Earbuds or over-ear headphones? 

Earbuds if I must

📱 Text or voice notes?

Text, I like precision

📸 Phone selfie or proper digital camera?

Leica forever

💡 Dark mode or light mode?

Dark mode

💄 Filters or no filter?

No filter

💳 Apple Pay or designer wallet?

Apple Pay

📺  Netflix marathon or TikTok scroll?

Netflix

📖 E-book or audiobook?

E-book

🎶 Spotify playlists or YouTube deep dives?

Spotify, currently loving the Jazz for Autumn playlist

🖥️ Desktop setup or laptop on the go?

Laptop on the go, although nothing beats working from a proper monitor