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

A selection of companies I advise. Please contact me for a access to the full list.

3D print high performance parts in the world’s most advanced thermoplastics and composites, including PEEK & ULTEM™.
Manufacturing
AI
Deep-Tech
Montreal
Series A
Airband develops unique dynamic sensing technologies to provide cost-effective mapping and monitoring of environmental factors.
Health
Environment
London
Pre-Seed

Atomic Machines

Atomic machines are nanoscale devices constructed from individual atoms or molecules that operate through controlled atomic-scale interactions to perform specific tasks.
Manufacturing
AI
Berkley
Series B

Boom Supersonic

Boom Supersonic is a commercial airplane manufacturer that builds supersonic airliners designed for speed, safety, and sustainability.
Transport
Denver
Series C
Bringing literature to life through conversational books. Rather than having a linear journey, interrupt and ask questions at any time.
AI
Culture
London
Pre-Seed
Giving parents another option. Freckle satisfies your child’s curiosity, and helps parents manage their safety.
Consumer
New York
Seed
Friend is an AI device company that offers a toy companion that boosts users’ self-esteem through positive conversations.
AI
Consumer
San Francisco
Seed
The global community for female entrepreneurs.
Community
Paris
Seed
Kindred is a members-only network for house sharing.
Travel
San Francisco
Series B

Lore / Drake Labs

Lore Cycling is a sportswear manufacturing company that creates custom road cycling shoes.
Consumer
Manufacturing
Sports
Salt Lake
Seed
Bringing Laser Beam Scanners, the next generation of display technology, to market.
Photonics
Deep-Tech
Itzehoe Germany
Series B
Delivering a non-invasive glucose monitor that delivers what the market demands.
Photonics
Deep-Tech
Health
Berlin
Seed
Radia is enabling the best onshore wind energy and cheaper green electrons – through a unique aerial transportation solution.
Transport
Environment
Boulder
Series B
Analogue processing to power the AI revolution.
AI
Processing
San Francisco
Pre-Seed
Additive Manufacturing
Manufacturing
Transport
San Francisco
Series B
Online support groups for any topic at a price everyone can afford.
Health
New York
Seed
Stardust is a cycle tracker that integrates science, ancient wisdom, astronomy and AI.
Health
Consumer
New York
Seed
Personal computing platform for an AI-first world, Wispr is redefining our relationship with technology.
AI
Consumer
San Francisco
Seed

Companies I have worked for

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

Consultancy

Ursa Major

Creative Direction
Creative direction for a new breed of rocket engine

Cabin

Creative Direction and Industrial Design
Industrial design and creative direction for Cabin on their new generation interior

Boom Supersonic

Creative Director
Creative Director, working on all design elements, including industrial design, brand design and direction, exterior loft, interior design and art direction

Creative and cultural projects

Robot Heart

Artist and fabricator
A new ‘back of the bus’ artwork for Burning Man 2019 Materials: PVC, Spandex

Stool no.1

Artist
I’ve been thinking a lot about the role of designers in the world since Covid-19. We need to do better, to think harder, and push ourselves into a new way of approaching projects. We are spoilt without supply chains, with the availability of any material we want. We don’t care enough about where these things come from, or how our products are finally shipped. I gave myself a brief of designing more with less, 3 materials (OSB, glue, and paint) to create a product and its packaging.

Fare Forward

Creative Direction and Build Lead
Not only was this the first time ever that the original Robot Heart bus came out of the desert dust, but the two days of performances we brought to Central Park’s Wollman Rink, was the first time live music was heard there in over 43 years, since The Pretenders last played in 1979.

Sonic Sphere @ The Shed

Creative Direction and Build Lead
The Sonic Sphere team works through rapid iteration. Conceived in the tradition of German composer Karlheinz Stockhausen’s Kugelauditorium, a nearly spherical concert hall built for the 1970 World Expo in Osaka, the sphere at The Shed is the 11th and most advanced sphere so far, after iterations of increasing size and technical sophistication, beginning at Chateau du Feÿ’s creative commune, and appearing since in London, Mexico, at Black Rock City, and in Miami.

Robot Heart Residency

Creative Direction and Build Lead
In November 2023, Robot Heart Foundation set out to bring a temporary community space to the Bay Area, with the intention of sharing music, art installations, educated conversations, a platform for youth to learn about electronic music, wellness, documentary screenings and dining.

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.