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Tech at the Gap 2025: Pioneering Possibility in Western Maryland

Posted on 8/20/2025

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Shaping the future of Western Maryland’s Tech Economy

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Tech at the Gap will return for its ninth year this fall, bringing industry professionals, students, and entrepreneurs from across the Mid-Atlantic to explore the future of technology in Western Maryland. Hosted by the Western Maryland I.T. Center of Excellence, Tech at the Gap 2025: Pioneering Possibility will be held on Thursday, October 16, 2025, at the Rocky Gap Casino Resort in Flintstone, Maryland.

What began as a small-scale event of around 100 participants has more than doubled in size, evolving into a top-tier regional showcase for innovation and technology. “It's hard to believe that we’ve been holding this conference for nine years,” said Autumn Becker, Executive Director of the Western Maryland I.T. Center of Excellence. “It's incredibly rewarding to see how we've grown and how we've fostered some great relationships. Some of which include our sponsors, Allegany County Economic and Community Development, TEDCO, and the Maryland Tech Council, which have been supporting us since the very beginning.”

Beyond its growth in attendance, Tech at the Gap has expanded in scope. Originally focused on highlighting tech trends in IT, the conference has evolved into a platform that elevates the broader entrepreneurial ecosystem of Western Maryland. “We've been able to highlight what's happening in the IT, tech, cyber, and AI industries,” said Becker. “But, we've found our niche in being able to highlight what's really happening in Western Maryland and what's unique to our region that makes us stand out.”

This year’s theme, Pioneering Possibility, emphasizes the importance of entrepreneurial thinking as a catalyst for innovation. The idea is simple: whether it’s applied within emerging tech startups or established organizations, adopting the entrepreneurial mindset empowers individuals to drive change, develop new solutions, and lead with agility in an evolving digital landscape.

“All of our keynote and breakout presenters are entrepreneurs in their own right,” noted Becker. “Or they've embraced that entrepreneurial spirit within the organization they work for—taking new, cutting-edge technology, a lot of times related to AI, and implementing it into their workplace. They're developing new products and new processes within their organization and really being key players in that realm.”

The same spirit extends to the next generation of innovators as well. While not designed specifically as a student conference, the event draws emerging talent and fresh ideas and offers a launching point for those looking to innovate, build, and contribute to the region’s growing tech economy.

Each year, Tech at the Gap features expert voices across cybersecurity, data science, artificial intelligence, and innovation. From seasoned executives to creative technologists, the conference offers insights that resonate with both creative technologists and emerging leaders. Here’s a preview of the dynamic keynote speakers who will lead this year’s conversations:

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Robbie Bach

Former Chief Xbox Officer and President, Microsoft, and Innovation, Leadership & Culture Expert

Robbie Bach spent 22 years at Microsoft, helping launch and grow cornerstone products like Microsoft Office before serving as President of the company’s worldwide entertainment and devices division. He has become a respected voice on strategy, civic innovation, and organizational culture.

“He is an entrepreneur, but he's probably best known for his work when he was at Microsoft,” said Becker. “He led the team that developed the Xbox. He is going to talk about the mindset, the discipline, and the principles he followed to develop Xbox and make it such a staple in the gaming industry.”

At Tech at the Gap, Bach will explore how bold leadership and team alignment drove innovation inside a massive tech corporation, and how that same mindset applies to today’s entrepreneurs and changemakers.

Tony Sager

Tony Sager

Senior Vice President and Chief Evangelist for The Center for Internet Security

Tony Sager has been a cybersecurity leader for over 47 years. Most of his career he spent at the National Security Agency, where he served as one of its first software vulnerability analysts and helped create two of its top cyber defense units. He is now Senior Vice President and Chief Evangelist at the Center for Internet Security, where he led the development of the widely adopted CIS Controls.

Sager’s talk will focus on “intrapreneurship,” driving innovation from within large institutions, highlighting true stories from his time at the NSA, where his team created tools, rewired processes, and advanced the mission despite rigid hierarchies and classification barriers.

“[Sager] presented in 2021, and everyone loved his talk about cybersecurity,” noted Becker. “Tony has some local ties, and he’s kind of a cybersecurity legend in the industry.”

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Cherry Rose Tan

Serial Entrepreneur & Venture Capitalist

Cherry Rose Tan is a fifth-generation entrepreneur, venture capitalist, and author. With 20 years of experience building, scaling, and investing in startups, she’s coached 350 companies across 27 verticals that have raised over $60 million in venture capital. She currently serves as Entrepreneur in Residence at the Schulich School of Business, leading an ecosystem of 250 startups focused on exponential technologies like Web3 and AI.

“Cherry is coming all the way from Canada to talk about being a minority in this field, and the mindset she’s had to carry herself through to be a successful entrepreneur,” said Becker. “Anytime I can highlight and uplift a female in the tech industry, I’m always excited to do that.”

Tan will share her raw and inspiring journey from hardships to success, offering a proven roadmap for becoming a “one percenter,” powerhouse leader in competitive, high-pressure industries without burning out along the way.

For those interested in attending the 2025 Tech at the Gap, an early bird discount is available through September 16. Visit the official conference website for more information on the conference speaker lineup, schedule, and more.

To learn more about what’s happening in Allegany County’s economic development space, read our blog here.

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