Steven M. May Jr. is the President and Founder of Ask the Egghead, Inc., a Washington, DC-based technology and business development firm he launched in 2015. With more than three decades of entrepreneurial leadership spanning technology, real estate development, construction, marketing, and enterprise sales, Steven has built a career around one central principle: growth must be intentional, strategic, and measurable.
At Ask the Egghead, Steven serves as Chief Egghead, leading business development strategy, high-level negotiations, and cross-functional collaboration across sales, engineering, and marketing teams. He specializes in identifying overlooked opportunities, whether new markets, new partnerships, or new service offerings, and converting them into revenue-producing initiatives. His approach is analytical and disciplined. He evaluates opportunity against cost, prioritizes based on return, and then executes with precision. The deals he structures influence not only immediate results, but the long-term direction of the organizations he serves.
Steven works closely with small and medium-sized businesses to develop acquisition strategies that strengthen profitability and operational efficiency. He maintains a vetted portfolio of vendor partners to ensure clients receive comprehensive solutions while maintaining high standards of quality and service. His strength lies in aligning internal teams and external partners toward a shared objective, then negotiating and closing agreements that create lasting impact.
In 2021, Steven founded the Slavic Art Alliance, a cultural organization dedicated to preserving and promoting Eastern Europe’s historic mosaic heritage. As Founder and President, he provides strategic oversight and leads initiatives to catalog, conserve, and showcase mosaic art across public and historic spaces. Under his leadership, the organization collaborates with artists, cultural institutions, and community partners to deliver tours, workshops, and exhibitions that connect communities to a shared cultural legacy. His work with the Alliance reflects his belief that leadership is not only about building companies, but also about preserving culture and contributing to something larger than commerce.
Steven’s professional foundation was built in enterprise sales and technology. As Vice President of Sales at Socrates Technologies, Inc., he helped scale the company into a major single-source integrator serving government, defense, and contractor clients. He expanded sales teams, opened new regional offices, established dedicated sales divisions, and helped guide the company through its transition to the public markets. His focus throughout was building scalable systems, disciplined teams, and sustainable growth.
In 1999, Steven founded SolarHost Corporation, a web services company powered entirely by solar energy, well before renewable-powered infrastructure became common. SolarHost provided hosting, programming, system administration, and database management services to hundreds of clients, many in the renewable energy and nonprofit sectors. He also implemented international development and support strategies to improve efficiency and service delivery across time zones.
Over the years, Steven has held senior leadership roles in real estate development and construction management, overseeing residential units, mixed-use development projects, and full-cycle construction operations. These experiences sharpened his ability to manage complex projects, coordinate diverse stakeholders, and execute under demanding timelines.
Beyond his professional work, Steven divides his time between Ask the Egghead’s Washington, DC, and Massachusetts offices. He lives with his wife, Sasha, and their three dogs: Beanie, a six-year-old Beagle; Yuna, a one-year-old Saint Bernard; and Rafael, a one-year-old Dalmatian. He enjoys spending time with his two sons, Christopher and Nicholas, and values the balance between building businesses and building a life grounded in family, loyalty, and long-term commitment.
Today, Steven continues to lead Ask the Egghead, Inc. with a focus on disciplined opportunity evaluation, cross-functional leadership, and sustained growth. Whether developing partnerships, guiding digital transformation initiatives, or supporting cultural preservation efforts, he remains committed to building organizations that are resilient, effective, and purpose-driven.