I'm Chester Chipperfield, a Creative Director and Advisor based in San Francisco, Jackson Hole and London. I focus on advising startups between pre-seed and Series B. I work with small creative teams around the world such as Berger & Föhr, Manual and Engraff and VC's such as YesVC, Pace, NFX, Shine and VSquared. Previously I have worked as the Global Creative Director at Tesla, Head of Special Projects for Apple, and VP of Digital Design for Burberry.

You can get in touch with me on LinkedIn or chesterchipperfield "at" gmail.com

Companies I advise:

Atomic Machines

Blackrock Neurotech

Boom Supersonic

California Forever

Lore / Drake Labs

Companies I have worked for

Juno

Co-founder and Creative Director
Overseeing User Experience, Art Direction, Brand and all other outward facing aspects of the company.

Apple

Head of Special Projects
Part of a small team overseeing all aspects of Apple Watch (including Product Development, UI, Hardware, and Marketing). I interacted closely with the ID, HI, Product Design, Marcom, Operations, Retail and Channel teams. Also involved in various confidential future projects.

Burberry

VP Digital and Interactive Design
I ran the Digital Design, Experience Design, UI, UX, and Platform Design teams, growing the digital department from 5 to 65 people over 4 years. Responsible for the design and direction of all owned platforms, as well as campaigns, product launches and retail. I was responsible for the company’s vision of the future of retail, being the strategic and creative lead on the Regent Street flagship store.

Tesla

Global Creative Director
Responsible for all customer facing visual elements of the company including store design, tesla.com, art direction, partnerships, merchandise, brand and communication globally. Collaborated on in car UI and the Tesla App. Worked closely with engineering teams on various projects both public and unannounced

More about me

I’m a multidisciplinary creative leader and advisor, working at the intersection of technology, design, architecture, and culture. Over the past two decades, I’ve helped shape some of the world’s most influential brands, from heritage fashion houses to next-generation energy, mobility, and AI companies.

My professional path began at the Bartlett School of Architecture in London, where I trained as an architect. I was drawn not just to buildings but to the systems, interfaces, and experiences that surround them. That curiosity led me, at 21, to found my first creative agency—a studio focused on digital experimentation, editorial design, and cultural storytelling. We worked with a range of forward-thinking clients including Tank Magazine, Saatchi & Saatchi, Antony Gormley, and the Wellcome Foundation, developing campaigns and platforms that blended design with narrative and emerging technology.

At 26, I joined Burberry, where I was tasked with building and leading the brand’s digital and interactive design function. Over four years, I helped scale the team from five to over sixty, working closely with Angela Ahrendts, Christopher Bailey, and Greg Stogdon. Our team spearheaded the reinvention of Burberry.com and pioneered integrated online/offline retail experiences, including the digital transformation of the Regent Street flagship. At a time when the fashion industry was just beginning to take digital seriously, Burberry’s approach became a benchmark for luxury brands worldwide.

In 2014, I joined Apple as Head of Special Projects, initially focused on the launch of the Apple Watch—Apple’s first new product category in over a decade. This role brought me into the heart of Apple’s product development ecosystem, offering a rare perspective across hardware, software, services, and retail. I worked cross-functionally with teams spanning Industrial Design, Human Interface, Retail, and Marketing, learning firsthand how Apple orchestrates its creative and technical disciplines.

In 2016, I was recruited via SpaceX to join Tesla as Global Creative Director. There, I oversaw all external and internal expressions of the Tesla brand. I led creative across digital platforms (including tesla.com and the Tesla App), retail store architecture, merchandise, and product storytelling. I also worked directly with Elon Musk and Tesla’s senior engineering leadership to evolve the in-car user interface and bring cohesion to the brand’s visual and experiential identity across all touchpoints. Tesla’s scale, speed, and ambition made it one of the most challenging and formative experiences of my career.

Since leaving Tesla, I’ve focused on building, advising, and investing in early-stage companies. I work with teams at the intersection of product, brand, and narrative—often acting as an embedded partner through critical inflection points like early fundraising, product-market fit, and launch.
I’ve co-founded and advised startups across sectors including real estate (Juno, Fabric Living), spatial computing and sound (Sonic Sphere), AI (Wispr, Reconceive AI), clean energy and aerospace (Boom Supersonic, Radia, Sakuu), and digital health (Invicta Medical, Running Tide). I also collaborate with forward-thinking venture funds like YesVC, NFX, Pace, Shine, and VSquared, helping portfolio companies align brand with product and purpose.

Beyond commercial work, I remain deeply engaged with cultural, artistic, and architectural projects. I contributed to the Sonic Sphere, a touring spatial audio venue inspired by Karlheinz Stockhausen’s spherical concert hall, and participated in the Robot Heart Residency—developing interactive art installations that merge technology and public space. These projects reflect my enduring interest in how design can shape perception, community, and experience.

I currently split my time between Jackson Hole, San Francisco, and London, staying close to nature while continuing to advise founders and build meaningful, creative infrastructure for the future.

I ski as much as I can, and moving through the mountains with friends is my happy place.