Cheryl Monroe
Cheryl Monroe is a decorated U.S. Army combat veteran, business strategist, and nationally recognized government contracting expert who has transformed the discipline and leadership gained from six combat deployments into a thriving entrepreneurial legacy. A retired Chief Warrant Officer Five, she made history through her distinguished military service, earning multiple leadership awards while managing complex operations in high-pressure environments.
She is the Founder and CEO of CK Management & Consultant Group, a strategic advisory firm she established to help small- and medium-sized businesses successfully navigate the complex world of government contracting. Through hands-on guidance in certifications, SAM registrations, capability statement development, proposal readiness, compliance systems, and operational optimization, Cheryl equips entrepreneurs with the tools needed to compete and win in federal, state, and local procurement spaces. Her firm specializes in positioning businesses for set-aside programs and supplier diversity opportunities, ensuring they are structurally prepared to scale. Through this work, she empowers entrepreneurs especially women- and minority-owned businesses to access procurement opportunities, build sustainable operations, create jobs, and generate generational wealth for their employees and communities.
She is also the Founder of The Cleaning Advantage, a commercial janitorial and facilities services company recognized for operational excellence, workforce development, and community-centered employment practices. Under her leadership, the company implements advanced compliance systems, industry-aligned service standards, and structured workforce training models designed to support both large public facilities and private-sector clients.
Beyond business, she is deeply committed to generational impact. She leads philanthropic and mentorship initiatives focused on financial literacy, STEM education, and youth empowerment. Through immersive programming and strategic partnerships, she equips the next generation with practical tools to build ownership, confidence, and economic mobility.
A sought-after speaker, panelist, and best selling author, She addresses audiences nationwide on leadership, procurement strategy, disciplined wealth-building, and legacy creation. Her work bridges military precision, entrepreneurial execution, and community empowerment demonstrating that government opportunities, when strategically leveraged, can become powerful vehicles for sustainable economic advancement.
Her mission is clear: build systems, create access, and turn contracts into legacy.
• Project Management Professional
• Webster University - MBA/HRM
• Sustainable Business Innovator of the Year award
• Women Elevating Women
• Wall Street Juniors Nonprofit Organization
What do you attribute your success to?
I attribute my success to the discipline, leadership skills, and institutional knowledge I gained during 28 years of military service, serving in global combat deployments as well as strategic assignments at the Pentagon and in NATO operations. Those experiences sharpened my ability to operate under pressure, manage complex logistics, and execute mission-driven strategies with precision. Combined with persistence, operational expertise in logistics and government contracting, and a deep belief in structure, systems, and process, I built a foundation that translates seamlessly into entrepreneurship. Success, for me, is the result of preparation, adaptability, and an unwavering commitment to excellence.
What’s the best career advice you’ve ever received?
The best career advice I’ve ever received was: “Master your craft before you chase the spotlight.”
That advice shaped the way I approached both my 28 years of military service and my transition into entrepreneurship. Titles, recognition, and revenue follow competence. When you invest in understanding the systems, the policies, the processes, and the people your foundation becomes unshakable.
I also learned to never walk into a room unprepared. Preparation builds confidence, and confidence creates opportunity. When you combine discipline, expertise, and integrity, your work will speak long before you ever have to.
What advice would you give to young women entering your industry?
My advice to young women entering the government contracting and strategic consulting space is simple: get in the room. Attend industry events, show up in government spaces, introduce yourself, and confidently claim your seat at the table. Relationships matter, and proximity creates opportunity.
Equally important, build your expertise. Learn the certifications, registrations, compliance requirements, and procurement systems required to successfully sell to government agencies. Master the structure behind the opportunity. When preparation meets visibility, doors open. Confidence is powerful, but competence is what sustains long-term success.
What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in government contracting today is the continued underrepresentation of women in procurement and decision-making spaces. While supplier diversity initiatives exist, access to information, relationships, and capital still creates barriers. Another significant challenge is the transition veterans face when moving from military service to civilian careers many have exceptional leadership and operational expertise but lack guidance on how to translate those skills into entrepreneurship or federal contracting success.
At the same time, the opportunity is tremendous. With over $800 billion spent annually in government procurement, small and medium-sized businesses that understand certifications, compliance, and strategic positioning are well-positioned to compete and scale.
What values are most important to you in your work and personal life?
The values most important to me both professionally and personally are service, impact, and legacy. Giving back to the community is not optional; it is a responsibility. I believe in mentoring others, openly sharing knowledge, and creating pathways so the next generation does not have to start from scratch.
I am deeply committed to fostering generational wealth not just for my family, but for employees and partners who grow alongside the mission. Inclusion matters, opportunity matters, and service remains at the core of everything I do. Success means little if it doesn’t uplift others.