WHO WE ARE
At FedWin Academy, our team of experts is dedicated to helping businesses win and grow in the federal marketplace. With decades of experience in government contracting, compliance, and business development, our instructors provide the knowledge and strategies you need to succeed.
Instructors
Guest Instructors
Monica Padron-Harris brings over 30 years of federal acquisition experience, including 21 years with the DoD/Navy and 12+ years at USCIS. As a Senior IT Acquisition Advisor, she supported both the Office of Information Technology (OIT) and the Office of Contracting (OCON), guiding strategic procurement decisions across complex IT portfolios. With deep expertise in DHS acquisition strategy, policy, and source selection, Monica offers FedWin Academy participants unparalleled insight into the federal contracting landscape—particularly within the Department of Homeland Security. Her extensive industry relationships and strategic approach to acquisition make her an invaluable voice in helping businesses understand how to navigate, compete, and win in the federal space.
Chris Hamm is the CEO of FIN Acquisitions LLC, an acquisition consulting firm that supports businesses navigating the federal market, from major defense contractors to tech startups and software firms targeting growth through GSA acquisitions. Chris and his team specialize in strategic consulting for large federal procurements, providing capture support and market positioning across both DoD and civilian agencies.
Previously, Chris served as a Senior Executive (SES) at GSA, where he led GSA’s Assisted Acquisition Services (AAS) for Defense—an organization that managed over $75 billion in active contracts. He was also GSA’s first Acquisition Innovation Advocate, recognized for championing non-traditional acquisition methods and fostering greater agility in federal buying.
Rip Singh the Principal Consultant at PrycePoynt Strategies. He is a innovative senior leader with a proven ability to win contracts in the Federal Health IT market. Skilled at intensive research to analyze client buying patterns, potential competitors, and a realistic assessment of contract costs for successful delivery. Interested in leading pricing strategy and business development efforts in the Federal Health IT market.
A former professional baseball player turned cybersecurity leader, Greg is an international keynote speaker and author of Cybersecurity for Everyday People. After a cyberattack wiped out his first company, he founded Valor Cybersecurity to help defense contractors build scalable, budget-conscious, and threat-adaptive programs. Greg delivered a top-level perspective on CMMC readiness and business considerations, offering practical insights into pitfalls to avoid and how to plan compliance without straining growth.
Lori leads a family-owned small business serving government clients since 1990. Having worked her way up from cleaning typewriters to running the company, she brings a hands-on understanding of leadership, technology, and small-business perseverance. Lori delivered a top-level perspective on the IT side of CMMC 2.0, helping GovCon leaders understand requirements and prepare effectively.
Todd Richards is the founder and CEO of Richards Procurement Group, with 34 years of federal service, including 30 years in contracting. A former U.S. Air Force officer and senior contracting officer, he spent over two decades at GSA supporting assisted acquisitions and major contract vehicles. Todd is the principal creator of OASIS, OASIS SB, and ASTRO and is widely recognized as a leading expert in IDIQ contracting and source selection. He has trained tens of thousands of acquisition professionals worldwide and is a frequent industry speaker and award-winning advocate for acquisition innovation.
Jacob is a seasoned accounting and government contracting professional with over 15 years of experience in accounting and more than a decade specializing in federal contracting. He holds a B.S. in Accounting from James Madison University and completed the Masters Academy in Government Contracting at George Mason University. His deep expertise spans DCAA/DCMA compliance, proposal pricing, and contract administration — making him a trusted resource for small businesses navigating the financial complexities of government work.
Carlos Fuentes is an accomplished government contracting executive with extensive experience driving strategic growth, building customer relationships, and supporting mission success across the federal marketplace. Throughout his career, he has partnered with government and industry leaders to develop innovative solutions that address complex challenges within the Department of Defense and civilian agencies. A graduate of William & Mary, Carlos combines a strong foundation in business with decades of experience in federal contracting. He currently serves in a leadership role at General Dynamics Information Technology (GDIT), where he focuses on customer engagement, strategic partnerships, and business growth initiatives that deliver measurable value to government clients such as Commerce, GSA, Labor, USPS, ED, USDA, Interior, HUD, FCC, SBA, and Legislative Branch agencies, among others.
Vik Singh is an accomplished government contracting finance executive with extensive experience developing financial strategies, building internal controls, and driving growth across the Department of Defense contracting industry. Throughout his career, he has helped government contractors manage indirect rates, incurred cost submissions, and financial reporting to support compliance and long-term growth. A graduate of George Mason University with a Bachelor of Science in Accounting, Vik combines a strong foundation in finance with over 20 years of experience in corporate finance and government contracting. He currently serves as Founder and Managing Partner of VSingh CPA LLC, where he focuses on FAR and CAS compliance, financial controls, and cost management initiatives that deliver measurable value to government contractors.
Tom is an accomplished government contracts attorney with extensive experience managing multimillion dollar government contracts from both within and outside the government. He understands the needs of all parties involved in a supply or distribution contract and uses his experience to negotiate on behalf of his clients regarding non-disclosure agreements, teaming agreements, reseller agreements, distribution agreements and more, with a focus on information technology and software procurement. In addition, Tom provides strategic guidance on Small Business programs, FAR/DFARS regulations, government expectations, compliance, and risk mitigation.