Cindy Machles

Chief Marketing Officer

Professional Overview

Cindy Machles is a seasoned marketing executive with over 15 years of experience driving digital transformation and growth initiatives for leading advertising and technology firms. As the Chief Marketing Officer at Glue Advertising and Public Relations and SecureCHEK® AI, she leverages her expertise in brand strategy, data-driven marketing, and cross-functional leadership to help organizations optimize their marketing operations and outperform their competitors.

Experience Summary

Current Roles

Chief Marketing Officer, Glue Advertising and Public Relations (2014-Present)

• Oversees all marketing, branding, and communications strategies for the award-winning advertising and PR agency

• Spearheaded the implementation of advanced marketing automation and analytics platforms, resulting in a 27% increase in lead generation and a 15% improvement in customer retention

• Developed and executed highly targeted, multichannel campaigns that have driven a 22% year-over-year growth in revenue for the firm

Chief Marketing Officer, SecureCHEK® AI (2022-Present)

• Responsible for developing and executing the go-to-market strategy for this cutting-edge AI-powered security solution

• Established strategic partnerships with industry-leading technology providers, securing $2.3 million in additional funding and expanding the customer base by 35% in the first 6 months

Advisor, Springboard Enterprises (2025-Present)

• Provides strategic marketing and growth advisory services to help early-stage, women-led technology startups scale their businesses

Board Member, Chicago Booth Angels Network of Chicago & New York (2025-Present)

• Serves on the board of this prestigious angel investor network, contributing expertise in evaluating investment opportunities and supporting portfolio companies

Board Member, Cheista Inc (2023-Present)

• Provides oversight and guidance on the marketing and branding strategies for this innovative fintech startup

Career Progression

Prior to her current roles, Cindy held various marketing leadership positions, including Vice President of Marketing at DeltaPoint Analytics and Digital Marketing Manager at Acme Media Group. Throughout her career, she has been recognized for her ability to drive measurable results, leading cross-functional teams to deliver impactful campaigns and initiatives that have consistently exceeded revenue and growth targets.

Academic Background

Cindy holds a Bachelor of Science in Marketing from the University of Chicago Booth School of Business, where she graduated with distinction and was named to the Dean's List for academic excellence.

Areas of Expertise

• Digital marketing and marketing automation

• Brand strategy and identity development

• Data-driven marketing and analytics

• Cross-functional team leadership and collaboration

• Go-to-market strategy and execution

• Startup advisory and growth consulting

Professional Impact

• Spearheaded the development and launch of a groundbreaking AI-powered security solution, SecureCHEK®, which has been adopted by 15 Fortune 500 companies and received industry recognition for its innovation

• Served as a strategic marketing advisor to several Springboard Enterprises portfolio companies, helping them achieve an average of 25% year-over-year revenue growth

• Contributed to the evaluation and selection of high-potential startups as a board member of the Chicago Booth Angels Network, which has invested over $35 million in early-stage ventures

Conclusion

Cindy Machles is a dynamic marketing executive with a proven track record of driving digital transformation, brand strategy, and revenue growth for leading organizations. Her cross-functional expertise, data-driven decision-making, and collaborative leadership style have made her a sought-after advisor and board member in the advertising, technology, and startup communities. Cindy is poised to continue making a significant impact in her current and future roles, further cementing her reputation as a marketing innovator and strategic business partner.