Small Business Week

MONDAY MAY 4TH

BUSINESS AWARDS CELEBRATION

Kick off Small Business Week by celebrating the outstanding businesses that make our community thrive. Join us for an evening of connection, recognition, and inspiration as we honor excellence & impact across the region.

TUESDAY MAY 5TH

HOW AI IS CHANGING MARKETING

Discover how AI is reshaping marketing. Join Jonathan Liebert & Taylor Draper as they discuss how to move beyond keyword marketing strategies & align with AI-driven intent based marketing.

Taylor Draper is the founder of Draper Company LTD, a performance marketing and lead generation agency specializing in helping businesses grow through Google Ads, Meta Ads, AI-driven automation, and conversion-focused strategy. With years of experience scaling campaigns across industries—from finance and real estate to healthcare and hospitality—Taylor focuses on helping small businesses move beyond traditional marketing tactics and build systems that generate measurable results. His work centers on combining paid media, AI tools, customer data, and automation to create smarter marketing that drives real revenue, not just clicks.

WEDNESDAY MAY 6TH

SMALL BUSINESS LISTENING TOUR

A collaborative session where small business owners share challenges and opportunities directly with policymakers. Lunch tables will be structured as working groups to facilitate meaningful feedback and discussion.

Moderator: Craig Carle, Vice President of Membership, Marketing & Events at the Colorado Springs Chamber & EDC, brings more than a decade of experience in strategic sales leadership, revenue growth, team development, and member engagement. As moderator, Craig will help guide the conversation with a people-first approach rooted in strong relationships, clear strategy, and practical execution. Known for building high-performing teams and creating cultures of accountability, empowerment, and pride, Craig is passionate about strengthening partnerships and supporting a thriving small business community in the Pikes Peak region.

Brian Risley, Colorado Springs City Council President Pro Tem, brings a deep understanding of local government, community planning, infrastructure, and economic development to his service on City Council. A Colorado Springs native and Colorado Springs Leadership Institute alumnus, Brian has spent years working at the intersection of civic leadership, architecture, land use, and public policy. His experience includes service on regional boards and committees, leadership with the El Paso County Planning Commission, and extensive work helping communities plan for responsible growth and secure funding for major public projects. Brian is passionate about bringing people together, listening to community needs, and finding practical solutions that support a strong and thriving small business environment.

Crystal LaTier, Economic Development Executive for El Paso County, leads a holistic approach to economic development across the Pikes Peak Region, supporting businesses, communities, housing, and long-term regional vitality. Her work focuses on strengthening a diversified economic ecosystem by leveraging business incentives, federal and state resources, community development tools, and strategic partnerships. Serving a region that includes eight municipalities and unincorporated areas across El Paso County, Crystal is committed to thoughtful, transparent, and collaborative economic development that builds trust and delivers meaningful impact. Through her leadership, the County’s Economic Development team advances programs, outreach, and initiatives that support a strong, resilient, and business-friendly environment for residents, entrepreneurs, and small businesses.

Jessie Kimber, Economic Development Officer for the City of Colorado Springs, brings extensive leadership, military, and economic development experience to her role supporting the city’s business community. A 24-year U.S. Navy veteran, Jessie has held command, executive, operational, human resources, and policy development roles, with deep experience building collaboration across diverse stakeholders. She previously served as Vice President of Defense Development at the Colorado Springs Chamber & EDC and as Special Assistant to former Mayor John Suthers. In her current role, Jessie works to strengthen Colorado Springs’ economic vitality by supporting business growth, attracting new opportunities, and helping create a vibrant environment for entrepreneurs, job seekers, and small businesses.

Commissioner Lauren Nelson, El Paso County Board of Commissioners District 5, brings a practical, service-oriented perspective to local government. A Colorado Springs native and proud District 11 graduate, Lauren was appointed to the Board of County Commissioners in June 2025 after serving on the Colorado Springs School District 11 Board of Education, where she focused on academic growth, fiscal responsibility, and community engagement. Before entering public service, she worked as a food scientist in product development, managing large-scale launches and cross-functional teams. Lauren remains active in the community through volunteer leadership, children’s ministry, and the Pikes Peak Philharmonic, and is committed to transparency, accountability, and supporting families, businesses, and residents across El Paso County.

THURSDAY MAY 7TH

PITCH COMPETITION

This exciting pitch competition will showcase innovative small businesses & startups leveraging AI to solve real-world problems. Attendees will hear live pitches from entrepreneurs competing for a $50,000 prize package of AWS AI services.

FRIDAY MAY 8TH

CLOSING CEREMONIES

Wrap up Small Business Week with a celebratory closing event. Reflect on the week, connect with fellow business owners & partners, & help us close out the celebration of small businesses.