Ola Olusoga

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A British, African, and American design executive, and product leader based in the United States.

Over the last decade and a half, I’ve designed experiences and led teams that work at the intersection of design, business, and technology. I have strong values, and believe in working cross-functionally, and in facilitating a communicative, high-trust, and autonomous work environment. When we set clear goals and well-defined expectations, we lay a path for strong outcomes and accountability.

I’m currently the Head of Design at CaptivateIQ.

Previously, Head of Design and Experience at WordPress.com, an Automattic company, where we work on creating experiences for over 43% of the web. I support the design and experience organization that works horizontally across the business to ensure the end-to-end experience is useful, usable, and desirable on all platforms (web browser, iOS, Android, and other devices).

Prior WordPress.com, I led the design team responsible for the WooCommerce mobile application, WooCommerce Marketplace, and shipping product. I cofounded a direct to consumer business called Populum where my cofounder and I bootstrapped the business from $0 to >$2.5M by helping people live healthier with quality, ethical, and honest CBD products . During this time, we scaled the business and team to support work across the value chain. Populum was eventually acquired.

Previously, I worked as a Design Director for Tuft and Needle where we help people sleep better. Spent some time agency side at Publicis.Sapient as a Senior Art Director working on brands like Diesel, Master Card, Lord Abbott, and other household brands, and early in my career worked at DDB Worldwide as an Art Director and Designer.

My start in design was through freelancing for different brands, businesses, and clients across print and digital mediums from websites to brochureware.

I support designers through a mentorship program with GrowthSpace.

Featured

2022 UX Design Trends w/ Proto.io

Convo with My Soulteam

Automattic Profile, The Muse

Guest Lecturer, University of Pennsylvania

Panelist, Remote Design week

Panelist, Tech Jobs Tour

Guest Lecturer, The College of New Jersey

Speaker, CMS Africa

Computation Art Director, Discussion w/ John Maeda

Featured, 28 Days of Web

Speaker, NABJ 2019

Interview with the CEO Library

Interview with Indie Hackers

Speaker, I-Beta Lisbon

Experience

Head of Design and Experience, WordPress.com
Jan 2017 – Present

Mentor, GrowthSpace
Feb 2021 – Present

Co-Founder, Populum
2016-2021 (Acquired)

Founder, CANNNY
2015-2016

Director, Design, Tuft & Needle
2014-2015

Sr Art Director, Publicis Sapient
2012-2014

Sr Art Director, DDB
2010-2012

Designer, Freelance
2004-2010

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