Craig J. Lewis: Empowering Gig Economy Workers with Efficient Payment Solutions

Ladderworks is a publishing platform of diverse picture books and online curriculum with the mission to empower over a million kids to become social entrepreneurs. Our current series features interviews by our interplanetary journalist Spiffy with inspiring Social Entrepreneurs, Entrepreneurship Ecosystem Builders, and Changemakers who are advancing the UN SDGs. 

Spiffy here! I’m back with the scoop on the entrepreneurial leaders of Planet Earth. As the only interplanetary journalist stationed on this blue planet, I’m thrilled to present this galactic exclusive with Craig J. Lewis, founder and CEO of Gig Wage. Let’s see what he is doing to make a positive impact in the world.

Spiffy: Thanks for joining me, Craig! Tell me, what challenge are you addressing at Gig Wage?

Craig: Thanks for having me, Spiffy! Gig Wage fills a crucial gap in the payroll market, catering specifically to businesses employing gig workers. Traditional systems, designed for W-2 employees, struggle with the unique needs of 1099 independent contractors. Gig Wage's platform offers flexible, efficient payment solutions, allowing for instant payments and streamlined administrative tasks, greatly enhancing worker satisfaction and organizational productivity. This innovation addresses the evolving demands of today's gig economy.

Spiffy: That’s amazing! What motivated you to do it?

Craig: I read a McKinsey & Company report on the growth of independent work—the gig economy. Uber, Lyft, and others had gotten the world’s attention and I realized other companies would need similar capabilities. Gig Wage was founded with the vision of modernizing the payment tools for the future workforce, accelerated by the explosion of the gig economy. The motivation lies in bringing innovation to an industry that has traditionally been slow to make the shift, with a focus on creating a service that is simple, fast, and easy for the on-demand workforce​​.

Spiffy: How would you say that your organization is working towards a more equitable world?

Craig: Gig Wage focuses on empowering gig economy workers, especially the underrepresented. In partnership with Green Dot Corporation and Commonwealth, we study financial interventions for these workers' security. We aim to support groups like Black, Hispanic, and female workers through inclusive financial products. We offer benefits like health insurance and tax tools, ensuring 1099 workers have access to W-2-like benefits, catering to the unbanked in the gig economy for their financial well-being.

Spiffy: Tell me about a recent organizational milestone or initiative. What impact does it make on your audience/community?

Craig: Gig Wage recently passed a major milestone of 600,000 independent workers signed up through the platform. In 2023, Gig Wage will have helped businesses pay out hundreds of millions of hard-earned dollars to independent workers in all 50 states and territories of the United States, and we will eclipse USD 1 billion in 2024.

Spiffy: Congratulations on reaching the milestone! Please share an experience when you faced failure and didn’t give up. What did you learn from it?

Craig: I personally bring toughness, urgency, grit, and agility to my role as the founder and CEO, honed on both the hardwoods as a pro basketball player and in meetings on Sand Hill Road in Silicon Valley. You are going to hear “no” a lot on the path to raising USD 20 million in venture capital and building a scalable technology startup. I have never had a “Woe is me” mentality. For me, it's about having resilience. I keep showing up and I keep figuring things out. Keep making the best next move!

Spiffy: Is there anything else you would love to tell our audience?

Craig: One of my biggest joys has been becoming an angel investor. Building and operating Gig Wage has given me a unique lens on entrepreneurship that I’ve been able to apply to funding other entrepreneurs. Being born to teenage parents in the projects, I never would have imagined I’d be an investor. Even thinking back to my earliest difficult fundraising days, I couldn’t have known that I’d one day be on the other side of the table writing checks. Investing provides a platform for me to have an even greater impact outside of what we are building with Gig Wage and I’m excited to lean into it even more.

Spiffy: Thanks for speaking with me today, Craig—it’s been an honor!

Craig J. Lewis is the founder and CEO of Gig Wage, a venture capital-backed Software-as-a-Service company that’s raised USD 16 million to date to meet the demands of the future workforce powered by modern payment tools. Craig prides himself on leading a fully distributed, remote team that is focused on building a high-growth and capital-efficient company. Gig Wage investors include Steve Case and his Revolution’s Rise of the Rest venture fund, Foundry, Green Dot Corporation, and more. Craig is also an active angel investor and a limited partner in various fintech and consumer packaged goods companies. Craig’s bold vision for innovation and audacious work ethic have pushed an antiquated industry to modernize and take better care of the independent workers that fuel their growth. (Nominated by Josef Scarantino at Hubspot Ventures. First published on the Ladderworks website on January 29, 2024.)

The views and opinions expressed herein are those of the interviewee and do not necessarily reflect those of Ladderworks LLC.

© 2024 Ladderworks LLC. Edited by Sujit Kunte. Spiffy’s illustration by Shreyas Navare. For the Ladderworks digital curriculum to help K-3 kids advance the UN SDGs, visit Spiffy's Launchpad: Creative Entrepreneurship Workshops for K-3 Kids and their caregivers here.