Anna Ondaatje

Anna Ondaatje is a seasoned brand strategy executive with a diverse background in creative direction and brand transformation. She most recently served as the Global Brand & Franchise VP of Strategy at Playboy, where she played a crucial role in leading a significant transformation of the brand over a three-year period that culminated in the company going public.2

Career Highlights

Current Roles::

• Founder of Red Notebook (since 2022)
• Head of LA Office & Creative Strategy at ReflexGroup (since 2023)1

Previous Positions::

• VP of Brand & Creative Strategy at PLBY Group (Playboy)
• Brand Specialist & LA Office Lead at Pramana Collective
• Strategist at Giant Spoon
• Digital Account Executive at Uplifted
• Fellow at The Wyss Institute for Biologically Inspired Engineering and the Programmable Nanomaterials Platform
• Mixing Board Founding Community Member
• Brand & Marketing Consultant at Earnin1

Education

Anna holds a Bachelor of Arts (B.A.) degree from Harvard University, where she majored in Comparative Literature with a minor in Visual & Environmental Studies and received a citation in Italian.1

Expertise and Interests

Anna is known for her ability to bridge the gap between business and creative teams, developing strategies that are both commercially viable and creatively expressive.2 Her work often focuses on complex brand transformations, particularly those with quantitative goals tied to significant business events like going public or being acquired.2

Throughout her career, Anna has demonstrated a keen interest in the representation of women in media and literature. This passion informed her academic work at Harvard and later influenced her professional choices, including her decision to work at Playboy.2

Anna is described as outspoken, curious, and detail-oriented, with a passion for brand strategy, art, and creative pursuits. Her expertise extends to shaping brand identities and strategies for more than 20 companies.

In her role at Playboy, Anna was instrumental in navigating the challenges of transforming a legacy brand, emphasizing the importance of consistency, open communication, and willingness to embrace change fully.2