Thanks to Rural Business Development Grants from the U.S. Department of Agriculture, Main Street America is working with three states — Wyoming, Kentucky, and California — to implement digital small business coaching programs. Wyoming Main Street’s program wrapped up in August 2025, providing business coaching support to 15 small businesses located in Douglas, Evanston, and Gillette. The communities were paired with an experienced coach who led educational sessions via in-person visits, ongoing virtual check-ins, and statewide webinars. Business owners left the cohort with stronger digital foundations, greater confidence to undertake their marketing efforts, and in some cases, pivots that reshaped business models. 

The program identified lessons and opportunities that can inform similar efforts across the broader Main Street America network. Here’s how to build your own digital coaching program that works, based on lessons from the pilot in Wyoming. 

1. One-on-One Coaching 

The defining feature of the program was its individualized coaching model. Each business received tailored advice aligned with its current business stage. Owners valued the chance to confidentially share challenges and test ideas with someone who understood their unique context.

This level of personalization built trust and ensured that progress was meaningful. Participants frequently cited accountability as the most valuable aspect of the program — knowing that they would be checking in with a coach motivated them to follow through on goals that might otherwise have been put aside by the day-to-day activities.

2. In-Person Visits

The program began with in-person assessments, and coaches noted how invaluable it was to see storefronts, team dynamics, and customer interactions firsthand. These visits provided context that simply cannot be captured in surveys or virtual meetings. Business owners agreed: several recommended adding a closing in-person session as well, giving them the chance to showcase progress and receive final feedback in person.

This bookend approach — starting and ending with in-person visits — would strengthen program impact, provide closure, and inspire continued commitment to growth. 

3. Build Flexibility into Your Program

We recognize that running a business requires adapting to shifting priorities. While most businesses were able to participate fully, a small number had to pivot their focus to manage critical needs like staffing shortages, seasonal demands, or personal matters. Coaches responded by developing a ​“Digital Presence Starter Guide” so even those who could not fully participate still received actionable tools.

The lesson here is clear: small business owners juggle many responsibilities. Programs must adapt to their realities by offering flexible timelines, supplemental resources, and recognition that even partial participation can yield long-term value.

4. Focus on Foundations

While many owners sought creative marketing or promotional campaign ideas, most first needed to strengthen their basic digital infrastructure. This included optimizing Google Business Profiles, cleaning up inconsistent online listings, and building user-friendly websites. Only after these essentials were addressed could more advanced strategies — such as AI-assisted marketing, loyalty programs, or cross-business collaborations — be effectively addressed.

Future programs should plan to dedicate significant early time to these fundamentals, ensuring a solid base before suggesting higher-level tactics.

5. Add Peer-Learning Sessions

Beyond individual coaching, statewide webinars allowed businesses to learn from one another and share ideas. Topics included leveraging AI, sustaining momentum after the holiday rush, and essential digital tools. While one-on-one sessions built depth, these group sessions created breadth and reinforced that businesses were not alone in their challenges. A combination of both formats proved highly effective.

6. Shorter, More Intensive Programs

The six-month structure worked well, but coaches recommended testing a three- to four-month intensive model with bi-weekly check-ins. This condensed timeline could help maintain momentum, prevent drop-off, and make it easier for business owners to commit during peak seasons. Scaling nationwide, this shorter format could also allow Main Street programs to serve more businesses annually.

7. Embed Coaches in the Onboarding Process

Some Wyoming participants entered the program without fully understanding its hands-on, time-intensive nature. Future programs could integrate coaches directly into recruitment and onboarding — through welcome webinars, orientation packets, or short pre-program interviews. Clear expectations from the outset would improve engagement, retention, and outcomes. 

8. Leverage Alumni as Mentors

The ripple effect of one business’s success on Main Street is powerful. In Wyoming, businesses that improved their digital presence often inspired their neighbors. A formal alumni mentorship component could extend this effect: past participants could serve as peer coaches or ambassadors, strengthening community ties and spreading knowledge at minimal additional cost.

9. Scale Knowledge Resources

The ​“Digital Presence Starter Guide” proved invaluable for disengaged participants and could be developed into a national resource. Main Street America could standardize such toolkits — covering core topics like Google optimization, website basics, and social media strategy — then adapt them for local contexts. This would ensure every business, regardless of participation level, benefits from a baseline of digital knowledge.

10. Balance Local Context with National Reach

The Wyoming program highlighted the importance of understanding local dynamics — foot traffic patterns, community culture, and even seasonality. Scaling nationwide will require balancing these hyper-local insights with universal digital marketing principles. A blended model, where national frameworks are customized locally, may be the most effective.

Why Digital Coaching Matters

At its core, the program demonstrated that digital readiness is now essential for small business resilience. Business owners who previously relied on traditional marketing saw the transformative power of Google reviews, targeted social media, and AI-enabled tools. Businesses that once struggled with visibility became destinations; others pivoted entirely into new ventures with confidence.

For Main Street programs across the country, expanding this model could mean equipping thousands of small businesses with the tools to not only survive but thrive in today’s hybrid physical-digital economy. By investing in coaching, training, and resources, the network can amplify local impact while building a stronger, more connected national ecosystem of entrepreneurs.

The Wyoming Digital Small Business Coaching on Main Street Program was more than a local pilot — it was a proof of concept. One-on-one coaching, grounded in trust and tailored strategies, produced results for businesses at all stages. In-person visits, accountability, and flexible resources enhanced outcomes, while group webinars and peer learning extended the value.