Failure is not an option with Cyndee Woolley

Cyndee Woolley is a prominent public relations executive and community leader based in Naples, Florida. She is best known as the founder and president of C2 Communications, a strategic marketing and PR firm she established in 2009.

Professional Career & Business

• C2 Communications: Cyndee leads this boutique agency, providing branding, strategic communications, and community outreach for local and international businesses, non-profits, and government agencies.
• Accreditation: She is an Accredited Public Relations (APR) professional, a designation signifying a high level of expertise in the field.
• Podcast Host: She is a frequent contributor to the Mission Matters podcast network, where she hosts interviews with business leaders and experts on topics ranging from AI and leadership to crisis communication.
• Author: She wrote the book Building Brand [You], which focuses on personal branding and has been used in academic settings, such as the MBA program at Hodges University.

Community Involvement in Southwest Florida

Cyndee is highly active in the Southwest Florida (SWFL) community:

• Keep Collier Beautiful: She serves as the Executive Director for this affiliate of Keep Florida Beautiful.
• Farm City BBQ: She is a key organizer for this long-standing annual SWFL tradition that bridges the gap between the business and agricultural communities.
• Leadership Collier: A graduate of Leadership Collier (2012) and Leadership Bonita (2009), she has remained involved as a board member for the Leadership Collier Foundation.
• League of Courageous Women: She founded this organization to empower professional women and foster community growth.

Notable Awards

• Naples Chamber Chairman’s Award (2018): Recognized for her significant support of the Chamber and its youth programs.
• 40 Under 40: Named to these lists by both Gulfshore Business Magazine and the Gulf Coast Business Review early in her career.

Cyndee is widely recognized as a “power player” in Florida communications, frequently speaking on how remote work, AI, and authentic storytelling are reshaping the industry in 2026.

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