SYDNEY ALLEN-ASH is a strategist and writer. Her practice is grounded in deep research and interdisciplinary collaboration. She likes working upstream, at the beginning of new initiatives, and is adept at steering major projects with many stakeholders from idea to execution.

Born outside of Toronto, Sydney studied Fashion Communication at Ryerson University. She joined Virtue, Vice Media Group’s creative agency, in 2016 as a social strategist managing a major telecom client. She grew quickly into a cultural strategist role where she was tasked with helping brands authentically and sustainably engage with communities. In 2019, she relocated to Vice’s New York City headquarters, where she led an effort to define Vice’s values for the first time in its 30-year history, redesigned the company’s onboarding protocols, led the development of Vice Media Group's first company website, and oversaw the development of an internal app designed to keep their global workforce connected to one another, to management, and to the work they produced together.

Since leaving Vice in 2021, Sydney has focused on projects that leverage her experience in transforming organizational dynamics while also providing opportunities for her to pursue subjects of special interest. In her writing and podcasting, she dives deep into the interstitial zones bridging athletics, race, history, equity, art, and popular culture. Sydney’s interest in podcasting developed out of her experience as a host and moderator—a role she’s taken on time and again in her career, moderating panel discussions, helming interactive workshops, conducting live artist interviews, and even hosting a short documentary produced for On Running.

Presently, Sydney writes and produces Toenails, a podcast about running, history, and the future of sporting culture supported by Ciele Athletics, and does a variety of freelance strategy, communication, and writing work.

Select Projects




Ciele Athletics

Condé Nast



Nomad Toronto


On Running




VICE Media Group



Toenails - A podcast about running and also not about running.

Work/Place - Exploring the futures of where and how we work.

Re:Search - Interviews on a wide range of themes.


BetterDone | VICE Media Group

Design For An Equitable Future | RGD Design Thinkers

DripKing & New American Sexy | From Later

In Talks with Es Devlin | HXOUSE

Internal Communications 101 | Bright + Early

Internal Innovation Workshop | adidas & Slow Factory

Importance of Execution Project Management Workshop | HXOUSE

Various Internal Talks | VICE Media Group

Yasin Osman and Jamal Burger | The Design Exchange

Year End Keynote | George Brown College School of Design