Skipper Chong Warson

Skipper Chong Warson

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Product discovery & design strategy • Turning customer signal into clearer product direction and better bets • Less “I think,” more “they said”
California, United States

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Jobs verified_user 0% verified
  • Karmascore
    Chief product officer (fractional)
    Karmascore
    Jun 2025 - Current (1 year 5 months)
    Advise the founding team on product strategy, design, and customer discovery for a relationship-wellness app.
    • Helped the team answer “Who is this for?” before committing to the next feature and framed its Bullseye Customer hypothesis through customer interviews
    • Turned observed behavior into clearer audience, positioning, and product decisions
    • Prioritized roadmap questions around customer evidence rather than feature momentum
  • How This Works co
    Principal advisor, founder
    How This Works co
    Aug 2024 - Current (2 years 3 months)
    Partner with founding and product teams on audience, positioning, product direction, and go-to-market decisions using direct customer evidence; personally lead interviews, synthesis, and decision-making working sessions.
    • Developed and delivered the Bullseye Customer Sprint and Listening Cycle; completed 11 Bullseye Customer Sprints, three separately scoped follow-on Listening Cycles, and seven other client projects
    • Bring founders, product leaders, and engineers into live interviews and debriefs so firsthand evidence shapes audience, positioning, product direction, and the next product or go-to-market decision
    • Led Replay’s engagement across five customer-hypothesis cycles, conducting 34 structured interviews within a bro
  • How This Works show
    Creator, host, and producer
    How This Works show
    Nov 2020 - Current (6 years)
    Create and independently produce an interview podcast built around a version of the question, “What do people do all day?” The show explores what people do, how they work, and what changed along the way. 35 episodes to date.
    • Own editorial direction, guest selection and outreach, research, interview preparation, recording, editing, publishing, and promotion
    • Season 1 ranged across work and craft; season 2 focused on product, design, research, facilitation, leadership, and organizational learning
    • Developing a third season about people building products, organizations, practices, communities, and creative work in real time
  • The Consulting Lab Inc
    Senior principal
    The Consulting Lab Inc
    Aug 2025 - Jun 2026 (11 months)
    Provided fractional product strategy and design support to organizations navigating growth and complexity, applying the same customer-evidence approach used through How This Works co across multiple markets.
  • SoftServe
    Regional design director - Americas
    SoftServe
    Jan 2021 - Jul 2024 (3 years 7 months)
    Led design strategy, business development, team growth, and consulting delivery for the Americas design group.
    • Directed an 18-month Duke Energy program with a six-person core team inside a 40-person group; led research and synthesis across 70+ initiatives and developed visual frameworks group leaders used to focus deeper work on roughly 20; shipped lab dashboards, project-tracking tools, communications templates, facility concepts, an implementation roadmap, and two working prototypes; turned an initial 12-week discovery into 18+ months of commissioned follow-on work for the Emerging Technology Office (ETO) 
    • Built and managed a distributed 12-person design team across the U.S., Canada, Mexico, Colombia, and Chile, including tw
  • thoughtbot
    Studio design director
    thoughtbot
    Aug 2019 - Dec 2020 (1 year 5 months)
    Helped lead a 20-person product development studio, directly managing three while shaping discovery, product strategy, and early-stage client engagements.
    • Co-managed staffing, project health, sales qualification, staff development, and studio operations, balancing team interest, project fit, client needs, and delivery risk
    • Co-led approximately 50 early-stage and enterprise opportunity conversations, helping founders and product teams clarify customer problems, product strategy, MVP scope, validation plans, design sprints, and proofs of concept
    • Helped steer the studio through COVID-19 disruption and the consolidation that followed
  • Sesame
    Founding product design director
    Sesame
    Sep 2018 - Aug 2019 (1 year)
    Joined as the first in-house design leader and led research, product design, prototyping, and design-system development as a direct-pay healthcare marketplace moved from early concept to conference demonstration and subsequent beta launch.
    • Ran 21 customer interviews and prototype tests before launch; combined live observation with Hotjar recordings to revise the booking flow, shopping basket, and other features within days
    • Built Macaw, a Figma design system connected to Storybook through Chromatic with the front-end architect; launched on schedule with approximately 500 providers in the marketplace by Aug 2019
    • Designed, tested, and iterated provider-side prototypes with a physician advisory council
  • Shep
    Founding product design director (fractional)
    Shep
    Apr 2017 - Dec 2021 (4 years 9 months)
    Worked ~10 hours a month as a fractional design and product lead through its shift into enterprise travel, the collapse of business travel, and its 2021 acquisition by Flight Centre.
    • Personally shaped design and product direction through work sessions, backlog reviews, and leadership meetings
    • Hired and directed two contract designers for the 2020 rebuild of Shep’s website, browser extension, and experience therein
    • Helped translate the company’s duty-of-care strategy into traveler guidance for health advisories, policy exceptions, emergency assistance, and traveler support integrated into the booking experiences travelers already used
    • Backed enterprise pilots with Adidas and Discovery Channel
  • Fjord Part of Accenture Song
    Senior service designer
    Fjord Part of Accenture Song
    Sep 2014 - Sep 2018 (4 years 1 month)
    Completed 20+ engagements across North America and Europe spanning customer research, service design, facilitation, product strategy, and opportunity framing for Accenture.
    • For a healthcare-financing client, led workshops and 10 customer interviews that showed uncertainty around timelines and approval mattered more than affordability; turned those findings into recommendations for clearer steps, flexible payments, and a more open application experience; the client business case projected a 10% increase in signups and approximately $2M in annual retained revenue
    • Led two Bank of America engagements: one unifying banker experiences across more than 10 business lines, and another consolidating three research applications into an i
  • Fjord Part of Accenture Song
    Senior visual designer
    Fjord Part of Accenture Song
    Aug 2013 - Sep 2014 (1 year 2 months)
    Led interface design and prototyping for Fortune 100 clients using Axure, Sketch, and InVision.
    • Worked across product and service-design teams to translate complex requirements into clear digital experiences
    • Helped organize a visual-design guild focused on peer learning, skill development, and career growth
  • s
    Web, graphic designer
    scw creative
    Jan 2011 - Aug 2013 (2 years 8 months)
    Delivered web, visual design, and illustration work for Rx.com, Keller Williams HQ, PBS FRONTLINE, and Mediabistro through direct relationships and partners including GSD&M, T3, Aquent, and directly. Recognized with Silver Addy Award and How Magazine Merit Award.
Education verified_user 0% verified
  • S
    Product, service & experience design
    Selected professional development
    Programs include Object-Oriented User Experience UX Masterclass (OOUX), Design Systems 101 (Design Systems University), Workshop Design and Facilitation (Hyper Island), Human-Centered Service Design (IDEO), and illustration coursework at the School of Visual Arts.
  • The University of Texas at El Paso
    Bachelor of Arts, Double major: Playwriting and English Literature
    The University of Texas at El Paso
  • AltMBA
    altMBA
    AltMBA
    Apr 2016 - May 2016 (2 months)
    One-month cohort-based leadership program developed by Seth Godin, completed in 2016. NYC community organizer 2016–2019 and active until it closed in 2024.
Projects (professional or personal) verified_user 0% verified
    Awards verified_user 0% verified
    • H
      Merit Winner
      HOW Magazine International Design Annual
    • American Advertising Federation
      Silver Addy Award
      American Advertising Federation
    Publications verified_user 0% verified
    • M
      Damien Newman’s “squiggle” as a critical look at design thinking
      Medium Oct
      In examining Damien Newman’s "squiggle" as a critique of design thinking, I contrast its messy, iterative process of creation with the structured steps often promoted by design thinking. I explore criticisms of design thinking's tendency to simplify innovation into a linear or "theatrical" process. A better way might be to integrate the structure of design thinking with the "squiggle" to better embrace uncertainty, foster iteration, and avoid performative innovation, leading to a more authentic problem-solving experience.
    • M
      Perfect is the enemy of done + get out of your own way
      Medium Dec
      Two of the four principles by which I best have done and, more recently, directed design work.
    • M
      Our go-to books for improving craft and quality in our design work
      Medium Dec
      With SoftServe’s design team dispersed across various locations globally, including the U.S., Ukraine, Bulgaria, Poland, Germany, Romania, the U.K., Singapore, Mexico, Colombia, and Chile, fostering effective collaboration while working remote (fully or partially) has become increasingly important. The rise of video calls, online workshops, and digital whiteboards has allowed us glimpses into our colleagues’ home and work environments, complete with human interactions, personal artifacts, plants, the occasional appearance of pets, and our bookshelves.

      Inspired by this, we pondered the question: as designers, what books do we keep on our respective shelves? Whether physical or digital, displayed for aesthetic purposes, a quick ref
    • M
      The mystique of innovation
      Medium Oct
      Innovation is often perceived as a sudden breakthrough, but in reality, it is a slow, iterative process of experimentation and refinement. The creative paths of individuals like Paul Cézanne, who took years to develop his mastery, contrast with prodigies like Pablo Picasso, highlighting different approaches to innovation. The distinction between "conceptual" and "experimental" innovators reflects how some succeed quickly with bold ideas, while others rely on persistent exploration. IDEO's framework of desirability, viability, and feasibility emphasizes that successful innovation combines creativity with practicality, and requires patience, self-management, and a commitment to continuous improvement.
    • M
      Practice, practice, practice makes…
      Medium Oct
      The constant drive for perfection is a ubiquitous aspect of our lives, fuelled by societal expectations and the need for external approval. However, perfection varies from individual to individual, making it a subjective and elusive target. Instead, we should focus on iteration and practice as the keys to achieving excellence. While the adage "Practice makes perfect" is well-known, it's repetitive practice, refinement, and growth that will result in mastery, an ongoing journey marked by continuous iteration and personal development.
    • M
      The art of embracing chaos: understanding creativity through the ‘squiggle’
      Medium Oct
      This article explores the creative process using Damien Newman's 'squiggle' as a metaphor for navigating chaos and uncertainty toward clarity. It emphasizes that creativity and problem-solving often begin in a state of disorder, but through iteration, collaboration, and adaptive thinking, patterns and solutions emerge. By adopting a mindset of "strong opinions, loosely held," individuals can confidently act in uncertain situations while remaining flexible to new insights, ultimately transforming chaos into actionable clarity.
    • M
      Unlocking collective power with workshops, HMWs, and BHAGs
      Medium Oct
      In this article, I emphasize the power of workshops, "How Might We" (HMW) questions, and Big Hairy Audacious Goals (BHAGs) as tools to tackle complex challenges. By creating structured, collaborative spaces, workshops empower teams to reframe problems, align on goals, and generate clear, actionable solutions. Also includes real-world examples, demonstrating how these methods lead to breakthroughs by combining ambition with a supportive, iterative process.
    • M
      The $2M insight: what 10 customer interviews found that a "data lake" missed
      Medium Jan
      Part of the Customer interviews 101 series, a Fortune 500 healthcare financing company — let's call them Acme Co — had mountains of data. Surveys, focus groups, polished personas, so data-rich they called their data lake a "double Baikal." And yet. Not one piece of it surfaced what Valerie told us from her car in a parking lot: she wasn't avoiding the service because she couldn't afford it. She was avoiding it because she couldn't see where she was going. No clarity on timelines. No answer to whether applying would hurt her credit score. No way to know if this was a smart move or a trap.

      7/10 people we talked to described variations of the same thing. The fix wasn't longer payment terms. It was transparency, dignity, and a clear
    • M
      Rethinking meetings, why they don’t work
      Medium Oct
      Meetings are often unproductive and consume a significant portion of work time, leading to frustration and diminished focus. To improve their effectiveness, strategies like setting clear agendas, encouraging asynchronous communication, using timeboxing to keep meetings concise, and establishing meeting-free days can be employed. Optimizing meetings in these ways can enhance collaboration and decision-making while freeing up time for deep, meaningful work. Insights from successful leaders show how purposeful and well-structured meetings can improve overall team productivity.
    • M
      Interviewing customers: the unsung superpower that your product company needs right now
      MEDIUM May
      Why product teams drift into assumption-driven decisions when they lose regular contact with customers—and why direct conversations about recent behavior remain one of the simplest ways to test what a team thinks it knows.
    • M
      Why I started How This Works co
      Medium Oct
      The launch story behind How This Works co: an advisory practice helping teams use customer interviews, shared evidence, and facilitation to make clearer product and strategic decisions. To celebrate, I'm sharing a specially curated mixtape.
    • M
      The real currency of lean research isn't insights — it's shared understanding
      Medium Jan
      Part of the Customer interviews 101 series, the most underrated part of customer interviews isn't what you learn. It's who's in the room when you learn it. At Sesame, we brought co-founders, engineers, our copywriter, and product managers into every other Fri session on the WeWork common floor. $20 gift cards. Under 10 questions. 21 people over three (3) mos.

      When a co-founder watches a user struggle with a flow directly, you don't need a report. You don't need a meeting. You already have alignment. Tomer Sharon calls it "shared understanding" — the collective knowledge that builds when a team learns together. That's what made a three (3)-month launch to JPM not just possible, but grounded.

      Who else on your team shou
    • M
      Understanding creativity, structure, and balance with Eames, design thinking, and Newman’s Squiggle
      Medium Feb
      Design isn't magic, though it can look that way. After stumbling across Charles Eames' 1969 design diagram during a conversation with Bumhan Yu on the How This Works show, I found myself reconsidering how we balance structure and intuition in creative work.

      Eames' diagram shows three overlapping spheres — client needs, design capabilities, and societal interests — with the sweet spot at their intersection. Unlike step-by-step frameworks, it's about navigating constraints with "conviction and enthusiasm."

      Comparing this with design thinking's structured phases and Newman's chaotic-to-clear "squiggle," I realized these aren't competing models but complementary maps of the same territory. Each illuminates different aspect
    • M
      Constructing the best pitches in football is as important as having safe spaces in our design work
      Medium Jul
      Drawing a parallel between groundskeeping in football (soccer in the U.S.) and the importance of creating "safe spaces" in design work, advocating for structured rituals like critiques, core values, and retrospectives to foster trust, collaboration, and quality outcomes in design teams.
    • M
      AI, generative AI, and machine learning walk into a bar — stop me if you’ve heard this one before…
      Medium Jun
      A 2024 explainer on artificial intelligence, generative AI, and machine learning, using metaphors to clarify how the concepts differ and where they were beginning to affect design, entertainment, and other fields.
    • M
      A lightweight framework for interviewing customers that actually works
      MEDIUM May
      Part of the Customer interviews 101 series, this article breaks down a lightweight framework that makes customer conversations practical rather than aspirational. After years of trial and error with teams, I've found what actually works: involve everyone (not just researchers) through watch parties where cross-functional team members observe interviews together; establish weekly touchpoints (even 15-minute calls count) to build rhythm rather than treating each session as a major event; ask questions about past behaviors ("Walk me through the last time you tried to solve this problem") rather than hypothetical futures; and combat data overload by documenting assumptions before interviews and capturing insights immediately after. The math mak
    • M
      How Margaret Gould Stewart and Adaptive Path helped me build and manage teams remotely
      Medium Dec
      Leading a remote design team up and down the Americas, I borrowed "attribute cards" from "Org Design for Design Orgs" by Peter Merholz & Kristin Skinner — simple cards showing traits we value in ourselves and teammates. What started as an experiment became our secret weapon for building trust across borders.
    • M
      Don't know where to start? Focus/task management and prioritization techniques to get sh*t done
      Medium Aug
      Exploring the myths of time management and offering practical techniques for prioritizing tasks and maintaining focus. Discover strategies like the 1–3–9 method, Cal Newport's "Deep Work," and the Pomodoro technique to help you get more done and stay productive. Includes links to books and other resources.
    • M
      What is a workshop and what it isn’t?
      Medium Oct
      This article explains the key differences between workshops and meetings, highlighting that workshops are hands-on, facilitated sessions designed for problem-solving, idea generation, and achieving specific outcomes. In contrast, meetings are generally more passive and focus on information sharing or decision-making. Workshops require active participation and structured facilitation, leading to tangible results like prototypes or action plans, whereas meetings are more suited for updates or quick decisions. Understanding when to use each format is crucial for optimizing productivity and collaboration in the workplace.
    • M
      A handful of thoughts on general artificial intelligence
      Medium Jun
      A 2024 reflection on artificial intelligence and general AI, including ethical questions and Roy Bahat’s framing of AI tools as looms, slide rules, or cranes — systems that automate work, extend human performance, or enable capabilities that were previously out of reach.