Scaling Smart: Navigating U.S. Expansion in 2025 & Beyond w. the Chamber of Commerce for Greater Philadelphia

As Manager of Business Attraction & Expansion, Lindsey builds coalitions of regional partners to engage and empower companies considering locating in Greater Philadelphia. She manages data analysis to help companies assess their business cases in the region and proactively attends conferences and trade shows to market the region. Lindsey holds a Master of City and Regional Planning and a Professional Certificate in Energy Management and Policy from the University of Pennsylvania’s Stuart Weitzman School of Design and its Kleinman Center for Energy Policy. Her professional background has touched regional planning, economic development research, campaign strategy, class action law, and tech hubs.

Nikisha Bailey is a community-driven entrepreneur, entertainment executive, and philanthropist committed to impact and change. She is the owner and operator of Win Win Coffee, Philadelphia’s first Black woman-led coffee roaster and distributor and the first coffee brand backed by supply chain technology to create a more streamlined, transparent, and sustainable industry. In 2024, Win Win Coffee was named a Top Product by Technical.ly and listed as a Top 10 Startup to Watch by the Philadelphia Business Journal. The brand was also handpicked by Goldman Sachs as a featured vendor at its 10KSB National Summit, where over 5,000 attendees enjoyed Win Win’s African blend from Ethiopia. Brand partners include PayPal, FedEx, Black Girl Ventures, The University of Pennsylvania, Oatly, and more.

Before entering the coffee supply chain, Nikisha spent over a decade in the music industry, serving as VP/Head of A&R Admin at Atlantic Records and leading A&R, marketing, and label operations. She has been recognized as a Billboard R&B/Hip-Hop Power Player (2020, 2021, and 2022) and was named to Forbes’ Next 1000 list for her entrepreneurial work. Additionally, she is a Trustee for The Recording Academy’s New York Chapter, an Ambassador for the Black Music Collective (BMC), and a founding member of CHIEF, a private network for women executives. She also teaches as a Professor at Drexel University’s Westphal Media Arts and Design Program.

“Community is everything,” Nikisha affirms. “You are only as strong as the team with you. I always want to connect people and draw on the power in numbers.

James Chester is the Co-founder and CEO of Gumband, an award-winning SaaS platform that allows brands to measure, control, and monitor their built environments in real time from anywhere. With his expertise spanning architectural design, marketing and tech, he has worked on multi-million dollar building and development projects, and led the digital transformation of Samsung's global media business at Starcom. In 2021, he launched Gumband as a product division out of Deeplocal, a creative technology and experience design company. Since then, Gumband has powered experiential activations and spaces for global tech and retail brands including Google, TikTok, Stripe, Meta, Activision, Nike and the NFL. James is most passionate about innovation, design, and technology. He is based in Nashville, TN.