Lesley Pinckney

Lesley Pinckney has spent two decades building brands, launching products, and figuring out what makes people pay attention. Now she runs The Big Idea Catalyst, a Chicago-based marketing and AI enablement consultancy that works with small and medium-sized business owners and startups on strategy, creative concepting, channel strategy, content, paid media, and creator marketing. Through The Big Idea Catalyst's AI For All workshop, she helps organizations move past the hype and put AI to work in ways that actually change how a team operates.

Her path to founding The Big Idea Catalyst ran through some of the biggest names in media and tech. At Intel, she led marketing for an AI robotics incubation group, managing everything from product research to go-to-market strategy for a portfolio of vision-based AI tools, including Intel PT Metrics, built to improve outcomes for physical therapy patients. Before that, she was General Manager of Essence.com, where she negotiated a joint venture between Time Inc. and Warner Bros. Television and turned the site into Time Inc.'s most profitable digital property per unique visitor, growing revenue 20 percent year over year. She got her start at MTV Networks, and later built two agency capabilities from scratch as Executive Strategy Director for GMR Marketing and the Omnicom Experience Group, work that earned her a spot in Omnicom University out of a pool of 70,000 employees.

Along the way she's led campaigns for Target, Nissan, Twitter (now X), US Bank, and Visa, including Target's influencer strategy for the Tabitha Brown collection. Whatever the brand, her focus has stayed the same: reaching young and diverse audiences with work that actually resonates rather than just checking a box.

Lesley writes What's Piqued Pinckney?, a newsletter for founders, CMOs, and SMB leaders that connects marketing, brand strategy, culture, and AI to whatever's happening in the news that week.

She's also a Black Venture Institute Fellow and an active angel investor. Lesley backs pre-seed, underrepresented founders building at the intersection of culture and utility, and she looks for founders who stay curious rather than ones who think they've already got it figured out. Her background in marketing, strategy, and technology gives her a sharp read on how startups scale authentically in the age of AI, and she tends to work closely with the founders in her portfolio, well beyond the check she writes, helping with customer insights, growth, and marketing strategy. Over time, she hopes to be known for backing the right people and being one of the good ones to have on your cap table.

She serves on the board of Near North Montessori School in Chicago and has spoken at SXSW, EventTech, the ANA, BlogHer, and the Mediapost Summit.

Lesley lives in Chicago with her wife, Tiffany, their daughter, Penelope, and their cockapoo, Ziggy. She's serious about food, in the eating and cooking sense, and will tell you about the night she had pancakes with DMX at a Las Vegas IHOP if you give her half a chance.