About Ryan Gentry Ryan Gentry is an entrepreneur, business strategist, and technology leader with more than a decade of experience scaling SaaS platforms in the telecommunications and marketing automation industries. As the CEO and Co-Founder of Drop Cowboy, he has built one of the most recognized platforms for ringless voicemail, SMS marketing, power dialers, and business automation tools. Recognized for his forward-thinking approach, Ryan combines technical expertise with a deep understanding of business growth and compliance in an evolving digital communications landscape. His leadership has positioned Drop Cowboy as a trusted solution for businesses of all sizes—from startups to enterprise organizations—seeking to engage customers with speed, efficiency, and measurable ROI. Entrepreneurship & Leadership Ryan’s entrepreneurial journey is rooted in solving real problems for businesses through innovative technology. His ability to anticipate shifts in telecom regulation and digital marketing trends has allowed Drop Cowboy to remain a leading platform in TCPA-compliant communication, automation workflows, and enterprise integrations. Beyond Drop Cowboy, Ryan is actively involved in building new ventures under Cowboy Concepts LLC, focusing on SaaS, automation, and accelerator opportunities that help entrepreneurs bring innovative technology to market. Areas of Expertise SaaS & Telecommunications Platforms Marketing Automation & Business Growth Strategy Ringless Voicemail & SMS Technology Compliance, FCC Regulations, and A2P Messaging Entrepreneurship & Venture Development Vision & Impact Under Ryan’s leadership, Drop Cowboy has helped thousands of businesses streamline communications, reduce costs, and grow customer engagement. His long-term vision is to continue expanding automation technology across verticals, enabling companies to scale smarter and compete globally.