We Are Category Designers

Al Head Shot

Al Ramadan



Mary Forman



Ashli Walkiewicz



Jason Wellcome


Carrie Drew Category Design

Carrie Drew


Brad Bio-1

Brad Drew


Christopher Lochhead

Chris Lochhead



Naomi Allen



Jennifer Johnson


Al Ramadan is the Founder and CEO of Play Bigger and co-author of “Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets”
He enjoys helping others achieve their full potential and pushing them to play bigger. He’s obsessed with technology and building categories, companies and products.

After almost 30 years of being an executive, he feels lucky to have discovered a role that suits his style. A supporting role, behind the scenes, for some of the greatest founders, teams and companies of tomorrow.

Building categories is a messy business. He is often involved in the ugly parts of category design as well as the glamorous ones.

Over the course of the last decade as a category designer he’s supported founders and teams create more than 50 new categories.

Al loves the alignment of Play Bigger's business model - we win by helping our portfolio companies win. 

Prior to co-founding Play Bigger, he enjoyed working with some of the great executives at Adobe Systems, Macromedia and Quokka Sports. Prior to that he was CTO for an Americas Cup campaign and founder of an Australian Software company.

He cut his teeth writing Fortran 77 on a PDP/11 and a Vax 11/780 and still writes the odd piece of Python code when necessary. He’s excruciatingly organized, focused on results and very data driven. He likes spreadsheets, charts and diagrams.

Al’s had the honor of being named as one of the most influential people in the digital economy by Time Magazine. He’s raced in the Americas Cup, taken multiple companies public, won big (and lost big), all the while never taking himself too seriously.

He loves the outdoors and still charges big waves and big mountain lines (for a guy his age!)

Mary Forman is our fearless Ringleader and she directs all aspects of Operations. As a member of the original Play Bigger team, she manages our cast of characters through every inquiry, project, event, and category outcome. Mary manages our client engagement process -- from scoping to overseeing strategic deliverables. If you need anything done at Play Bigger, ask Mary. 

Before Play Bigger, she was a Corporate Concierge for Spieker Properties, Sun Microsystems and American Express. Starting in college, Mary earned her stripes in the hospitality industry managing some of the hottest Bay Area restaurants and hotels.  Mary has a bachelor’s degree in Business Management from Santa Clara University. 

When she’s not Playing Bigger, Mary can be found picking fruit on her family’s farm, planning high touch events, running the PTA, taking or teaching Pilates, and keeping up with her three spectacular children. Mary is a San Francisco Bay Area native with a fabulously wicked sense of humor.

Ashli Walkiewicz is a Category Designer In Residence and specializes in Strike Execution. She has led strikes at Play Bigger portfolio companies including Livongo, Domino and Clear Metal. She is an energetic, motivated multi-tasker who can wear many diverse hats simultaneously and is not afraid of a challenge.  Ashli truly takes the bull by the horns - no matter what her exact role is - with her southern charm and always exceeds expectations. Prior to Play Bigger she had an impressive 20-year career in traditional and digital marketing working with start-ups and Fortune 500 companies.  When she isn't telling folks how passionate she is about category design, you can find her spending quality time with her husband Scott and her adorable mini bernedoodle, Dunkel (his full name is Munich von Dunkelstein if you wanted to know).  

Jason Wellcome is a Category Designer who brings nearly two decades of experience driving transformative work for leading communications agencies, technology companies, global consumer brands, and fast-growing startups.

Born and raised in the Pacific Northwest, Jason was captivated by the region’s flourishing tech scene and worked on launch efforts for start-ups during the first dot-com boom. He eventually found his way to global PR giant, Weber Shandwick, where he worked closely with companies like Microsoft, Toshiba, and Universal Pictures to create new categories for entertainment in the digital era.

Jason believes the pace of today’s technology-led change requires a bias for continuous learning and transformation — on both a personal and organizational level. This led him to New York City where he spent much of the past 10 years reshaping the communications landscape and establishing a new category-defining capability, Mediaco. Ultimately the allure of west-coast living pulled Jason back to his native coast to lead the go-to-market function for a fast-growing software startup focused on supply chain.

When not obsessing about new opportunities for Category Design, Jason loves to hike with his rescue pup, Harley, and add to a growing list of 30+ countries explored with his wife.

Carrie Drew began her career at legacy brands Quiksilver and Volcom, giving her a strong foundation in product design, production, and apparel construction. Later, she travelled the world while working as the Lead Graphic Artist for O’Neill, PacSun, and Urban Decay Cosmetics, before becoming the Senior Art Director for Fox Racing, Inc.

Carrie’s last full-time role as the Global Art Director for Rip Curl, Inc. spanned just under a decade. She produced hundreds of textile prints, graphics, and apparel which you can find in stores and online today.

Just after starting a Boutique Creative Agency with her husband Brad six years ago, Carrie launched her first Lightning Strike by going to market as an exhibitor with a collection of original art at the PrintSource Textile Show in New York.

Carrie loves inventing new ways to tell stories through the prism of Art and Category Design. When she's not working in her studio, she's tending to her garden, cooking colorful recipes, working with horses, and foster-parenting babies.

Carrie and Brad Drew are a husband-and-wife team from Southern California who lead Play Bigger’s in-house Creative Agency. Together, they possess a uniquely broad set of skills which allow them to solve problems for us, and ultimately our customers.

Brad Drew has 15+ year’s experience within the Film, TV and Media realm and owned his own content production company for nearly a decade. Brad began his career working at Surfer Magazine and the Los Angeles Times where he traveled the world as a freelance writer before moving on to an Editorial Director role at a groundbreaking desktop publishing company. Brad led the Marketing Departments at Ambiguous Clothing and Rusty Apparel -- where he helped execute numerous Lighting Strikes – before branching into TV production. Working as a Sports Emmy-nominated writer and producer, Brad’s produced programming for Fox Sports, NBC Sports, FUEL TV, Red Bull Media House, Monster Energy, and many others. He worked as a Webby-nominated senior producer for both Network A and Nitro Circus and was writing and producing content for pro surfing's World Surf League before taking a leap and joining creative forces with his wife. 

Brad loves inventing new ways to tell stories through Category Design. When he's not neck deep into a project, he's enjoying a day at the beach, golfing with friends, adventuring with their dog Bandit, and planning the next trip.

Christopher Lochhead is a co-founder of Play Bigger and co-author of “Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets”

Today he’s a #1 Apple Podcaster and one of the “godfathers of Category Design”. He has been a Category Design advisor to over 50 venture-backed startups, is a venture capital limited partner investor and a former three-time Silicon Valley public company CMO (Vantive, Scient, Mercury), and entrepreneur.

On rare occasions he helps design categories with Play Bigger portfolio companies.

Naomi is a member of our Category Designer in Residence program. She brings two decades of experience to the intersection of healthcare and technology. She’s helped companies like Kaiser, Microsoft, Yale Hospitals, HP and myriad others on their digital health and technology strategies.

Early in her career she worked in hospital operations and enterprise resource planning at Deloitte Consulting, which led to her love of technology enabled healthcare. After receiving her MBA at Stanford, she helped build McKinsey’s healthcare technology practice on the West Coast.

She was a founder for Castlight Health and ran most of the business teams during her 8 years tenure — taking the company from an unformed idea with seed funding to IPO. Naomi ran Strategy, BD, Sales, Professional Services, Product and Operations during her time at Castlight. During that time, she developed Castlight’s first data rights with payors, landed Castlight’s first customers, hired and built the enterprise sales team, led the company from a single product to an enterprise platform, led the Series A-1 and B financing, and participated in the IPO roadshow. She also helped develop (and received) two patents, lectured on digital health at business schools and in the media, and became a thought leader on enterprise healthcare. She was instrumental in the Category Design process with Play Bigger, creating the Enterprise Healthcare Cloud and launched the category at Castlight’s first category lightning strike.

After Castlight, Naomi, her husband and their three kids took an epic adventure -- visiting 22 countries in 14 months. Now back at it, she is excited to return to her technology and startup roots, helping world-class companies develop their Category and POV.

Naomi is currently the CEO and Co-Founder at Brightline. 

JJ is Play Bigger’s first Category Design in residence. She believes category design is the missing link in the CMO’s arsenal - articulating a problem that didn’t exist before and conditioning an entire market to adopt a new and different way of working or living. And that those who embrace it will win in this new era.

Born and raised in Wisconsin, JJ grew up around her family business, a 70 year old level and tool manufacturing company founded by her grandfather and now led by her father. At a young age she was ingrained with the values of a strong work ethic, a sense of urgency, and a relentless ability to succeed even faced with the most challenging of circumstances. JJ has lived in San Francisco for almost 25 years now, but will always keep the foundation of her upbringing at the core of her leadership style. This has served her well in CMO roles at high-growth start-ups including Coverity and Tanium, as well as a year in between as a partner at the venture capital firm Andreessen Horowitz. Prior to being CMO, JJ held product marketing and marketing roles at enterprise software giants including Veritas Software, Symantec, Mercury and HP Software.

When not designing categories, JJ loves to travel, play tennis (she is a lefty with a mean backhand) and is a huge football fan (she even loves the 49ers when they are as terrible as they are now).

In October 2020, JJ joined Amplitude as its first-ever Chief Marketing and Strategy Officer.

Brand Ambassadors

Bianca Bio

Bianca Valenti





Bianca Valenti is a professional big wave surfer, Italian wine specialist and Changemaker. She plays to win. And her victories extend beyond the water. She’s recognized as a champion for winning equal pay and access for women in professional surfing. Bianca is Play Bigger’s first Category Design Brand Ambassador, and she developed the Women’s Big Wave Surfing category alongside three of the world’s top female big wave surfers.

Possessing a rare ability to navigate risk with remarkable composure and elegance, Bianca breaks barriers in and out of the water. Named one of Outside Magazine’s Most Accomplished Athletes in 2018 (alongside climber Alex Honnold and tennis champ Naomi Osaka), her surfing performance and advocacy work has been highlighted in the New York Times Magazine, BBC World News, ESPN, Surfer Magazine, and the San Francisco Chronicle, among other outlets. 

As a Category Designer, entrepreneur, public figure and leader, Bianca selectively works with partners who stand for excellence, environmental stewardship, equality and equity.

She volunteers with Brown Girl Surf and MeWater Foundation to ensure the next generation of female surfers can experience the stoke and awe-inspiring power of the ocean. And as an ambassador for Save the Waves Coalition and Sustainable Surf she contributes to ocean-positive, surf ecosystems at home and abroad. 

When not tackling Mt. Everest-sized waves, Bianca hosts wine tastings as an Italian wine specialist. A graduate of UC Santa Barbara with a bachelor’s degree in Global Studies and Sports Management, she went on to study with the Association of Italian Sommelier to become an Italian Wine Specialist. She co-owns Valenti & Co Ristorante Vinobar in Marin County and lives in San Francisco, where she can be found surfing two notoriously scary big wave breaks -- Ocean Beach and Mavericks. 



Hi, I am Skittles. I don’t listen to Dave or Al. I am Play Bigger’s plutonium and make all the decisions around here.

Woof! — (translated to Play Bigger!)

We're Hiring //

Category Designer in Residence


Two open positions