Chester Chipperfield — Creative Director & Advisor
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 and Founders I Advise
AON3D
Randeep Singh
LinkedInAtomic Machines
Jeff Holden
LinkedInBoom Supersonic
Blake Scholl
LinkedInCalifornia Forever
Jan Sramek
LinkedInFabric
Clare Laverty
LinkedInChester Chipperfield
Friend
Avi Schiffmann
LinkedInKindred
Kinship
Hana Azab
LinkedInKnown
OQmented
Quantune
Radia
Mark Lundstrom
LinkedInReconceive AI
Charlie Buchbinder
LinkedInShareWell
CeCe Cheng
LinkedInSkyway Private
Adam Schuit
LinkedInWispr AI
Advisory Thesis
Investment Principles
I back founders who are building category-defining companies at the earliest stages. I look for strong thesis-driven conviction, unique market insight, and the ability to execute against a bold vision.
Company Criteria
I favour technology-enabled businesses with defensible moats: proprietary data, network effects, or deep technical IP. I also selectively back consumer brands in CPG, health, and wellness where the founder has genuine domain expertise and a differentiated product. I avoid pure services businesses without a scalable platform component.
Founder Criteria
I look for founders with unfair advantages: deep domain expertise, prior startup experience, technical depth, or unique market access. Coachability, resilience, and intellectual honesty matter as much as pedigree.
Target Industries
My core sectors are: Consumer Technology, EdTech, HealthTech, Digital Wellness, CPG/D2C brands, deep tech requiring 10+ year timelines, and industries where regulatory risk is the primary moat.
Companies I have worked for
Tesla
Global Creative DirectorResponsible 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
Apple
Head of Special ProjectsPart 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 DesignI 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.
Juno
Co-founder and Creative DirectorOverseeing User Experience, Art Direction, Brand and all other outward facing aspects of the company.
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 unify 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.