EO Charleston Member Spotlight: Will Pearson

From Indianapolis to Silicon Valley to Charleston, Will Pearson's journey exemplifies innovation, adaptability and perseverance. This feature delves into his background, experiences and insights, offering valuable lessons for aspiring entrepreneurs.

The Genesis of an Entrepreneur

Will Pearson grew up in Indianapolis with a burgeoning aspiration to start his own company. After graduating, he joined Target's corporate headquarters but soon realized the corporate world was too vast and impersonal for his entrepreneurial spirit.

Driven by a desire for technological innovation, Will moved to San Francisco and joined Vivino, a wine app startup. At the time, Vivino had around 5 million users but no revenue stream. As one of the first eight employees in the San Francisco office, Will helped transform Vivino from a user-centric app to an e-commerce powerhouse, scaling the revenue from zero to $200 million.

This experience ignited Will’s deeper desire to start his own venture. In 2019, Will co-founded a new company specializing in email marketing software with Brant Cebulla, a colleague with aligned ambitions, drawing on their extensive experience with email marketing at Vivino.

Evolution of the Business

The initial vision was to create a software tool to help companies collaborate and build emails efficiently. After securing venture capital, the two began developing their software. However, they soon realized their target market—large enterprises—was hard to penetrate as a nascent startup.

Faced with challenges, Will and Brant pivoted their business model to start an email marketing company, Scalero. They shifted from pure software development to offering tech-enabled services, managing email marketing strategies, design and execution. This pivot allowed them to generate revenue without relying solely on outside investors. They developed internal tools like Tiramisu and Cannoli, streamlining email production and collaboration.

Personal Growth and Business Milestones

Since starting Scalero, Will has experienced significant personal growth. Becoming a father in October 2020 has profoundly shifted his perspective, teaching him to prioritize family over work. Moving from San Francisco to Charleston further enhanced his quality of life, showing how entrepreneurship can offer a better work-life balance.

Under Will's leadership, Scalero achieved a global presence, working with clients from diverse backgrounds and industries. Notably, they landed Notion as a client, leveraging their use of the tool for project management to offer email marketing services. This partnership has been mutually beneficial, exemplifying the power of strategic collaborations.

Industry Insights and Future Outlook

Will believes that email marketing will continue to be a vital revenue channel for businesses. The industry must evolve to meet consumer expectations for personalized experiences. AI and machine learning will play significant roles, enabling marketers to understand and cater to individual consumer profiles more effectively.

To stay ahead in the rapidly changing landscape, Will emphasizes continuous learning and adaptation and believes that entrepreneurs must pivot and adjust strategies in response to market feedback and emerging trends. Building a sustainable business requires focusing on profitability and financial stability rather than relying solely on external funding.

Reflections and Advice for Aspiring Entrepreneurs

In the early stages, Will and his team frequently encountered clients who loved their work and wanted additional services. Initially unprepared for this demand, they built a freelance network to complement their core offerings, allowing them to meet client needs more effectively. This adaptability and willingness to expand their service model have been key to their growth.

Reflecting on his journey, Will acknowledges that the 'Silicon Valley mindset' of prioritizing revenue growth over profitability can be risky. He advises aspiring entrepreneurs to consider profitability early on to mitigate financial stress. 

He also highlights the importance of not overthinking the initial business idea. Taking the leap and starting the journey is often the most crucial step, and ultimately, Will believes, “It’s all part of the journey.”

Will encourages new entrepreneurs to leverage their networks and seek support. He advises, “Reaching out for introductions and advice can open doors to valuable opportunities. Even if the initial venture doesn't succeed, the experience gained will be invaluable for future endeavors.”

Joining EO and Facing Challenges

Will's journey with EO exemplifies that entrepreneurial success doesn't always require building a massive tech company. By focusing on a specific niche and delivering exceptional value, entrepreneurs can achieve significant success and recognition.

The Road Ahead

Looking forward, Will Pearson remains optimistic about the future of his business and the broader industry. By staying attuned to technological advancements and consumer expectations, he plans to continue delivering innovative email marketing solutions that drive client success.

For aspiring entrepreneurs and business owners, Will's story is a powerful reminder that success is a journey of continuous learning, adaptation and perseverance. Whether you're just starting or looking to scale your business, the lessons from Will's experience can provide valuable guidance and inspiration.