Small Business Development Services
Practical Support for Small Business Success
Navigating Complexity with Experienced Guidance
Creating Tomorrow's Workforce provides small business development services tailored to the unique challenges of working with public agencies. Whether it’s preparing for a government contract or navigating internal operations, our goal is to help small businesses compete and thrive. With a background that includes leading small business support programs within city and regional government, Greg Wolley brings deep expertise in the processes and relationships that underpin successful small business growth.
Greg has helped businesses understand and overcome the hurdles of public procurement and professional services contracting. His support has included coaching on proposal development, offering strategic insights into teaming and subcontracting, clarifying insurance and bonding requirements, and helping businesses build and maintain professional relationships with agency project managers.
At Creating Tomorrow’s Workforce, we know that the public sector can be a powerful client and partner for small business, and we aim to ensure that more diverse and local businesses can access those opportunities.
Government-Focused Business Support
Demystifying the Public Sector
Many small business owners are unfamiliar with the language, structure, and culture of government contracts. We help demystify these systems and prepare our clients to enter them with confidence. Our services include:
RFP and proposal development coaching
Assistance in understanding government procurement processes
One-on-one coaching sessions
Outreach strategies to connect with agencies
Capacity-building for small and emerging firms
Greg’s experience includes supporting businesses in Portland and beyond with services designed to build long-term capacity and readiness. While working at TriMet and the City of Portland, Greg implemented strategies to help local businesses remain resilient through major infrastructure projects and shifting procurement landscapes.
Our approach is not just about documents and deadlines, it’s about building trust, confidence, and readiness for long-term success.
Creating Stronger Teams Through Collaboration
Connecting People, Building Partnerships
One of the most under-leveraged strategies in small business success is collaboration. Creating Tomorrow’s Workforce helps entrepreneurs develop strong teams and partnerships that allow them to scale, share resources, and deliver on larger contracts. We provide:
Facilitation for team-building meetings
Strategic matchmaking for partnership opportunities
Support in understanding roles and scopes within joint ventures
Coaching for clear and effective communication across partner organizations
Greg’s network and facilitation experience make him a valuable connector, able to help businesses navigate both internal growth and external relationship development. He believes in the power of relationships, and he applies that philosophy to every partnership and team he supports.
In a competitive landscape, it’s not just what you know…it’s who you know and how you work together. Creating Tomorrow’s Workforce helps small businesses unlock that potential.
More Services
Workforce Development Planning & Support
Creating Tomorrow’s Workforce offers customized workforce development planning and support, helping organizations design inclusive, sustainable employment pipelines that reflect the communities they serve.
Coaching and Public Speaking
Greg Wolley offers leadership coaching and dynamic public speaking services rooted in real-world experience, equity, and community empowerment. From one-on-one sessions to keynote talks, he helps individuals and organizations move from ideas to meaningful action.
Non-Profit Strategic Plan Implementation
Creating Tomorrow's Workforce helps non-profits transform strategic plans into actionable implementation frameworks. From DEI and outreach to recruitment and hiring, Greg Wolley ensures your vision becomes a practical and impactful roadmap.
Youth Career Education in Natural Resources
Hands-on youth career education in natural resources. Creating Tomorrow’s Workforce helps organizations design impactful programs that engage, educate, and inspire future environmental leaders.
