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.


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Teaming up with the best in Oregon

Teaming up with the best in Oregon

Teaming up with the best in Oregon

Let's Build a
Better Future Together.

  • Inclusive

  • Strategic

  • Grounded

  • Impactful

  • Collaborative

  • Sustainable

  • Purposeful

  • Empowering

Let's Build a
Better Future Together.

  • Inclusive

  • Strategic

  • Grounded

  • Impactful

  • Collaborative

  • Sustainable

  • Purposeful

  • Empowering

Let's Build a
Better Future Together.

  • Inclusive

  • Strategic

  • Grounded

  • Impactful

  • Collaborative

  • Sustainable

  • Purposeful

  • Empowering