About
AI-Native. Operator-Led.One mission.
Two former CMOs building AI-native marketing transformation. We've led global brands, taken companies public, and driven billions in growth. Backed by a world-class team, we bring the experience, clarity, and speed that transformation demands.
Why We Exist
Trust
No vendor agendas. No agency spin. Just straight talk, tested strategy, and proven results. We've been CMOs — not career consultants. We know the decisions, the deadlines, and the boardroom pressure firsthand.
Time
Marketing transformation devours the one thing you don't have: time. We give it back. From audits to workflows to pilots, we accelerate what usually takes quarters into weeks. Our roadmaps move fast, so your team can focus on impact, not firefighting.
Leadership
Led by operators. Backed by a team.
Behind Shiv and Ben is a handpicked team of strategists, technologists, marketing practitioners, and purpose-built AI agents who bring deep functional expertise across every engagement. We don't outsource the work — our team, human and AI, is in the trenches with you.
Shiv Singh
CEO, Savvy Matters
Shiv Singh is CEO of Savvy Matters and a business leader and advisor with more than two decades of executive experience in marketing, innovation, and growth at global companies including Visa, PepsiCo, LendingTree, and Expedia Group. His work focuses on helping organizations build enduring brands while navigating transformation in the age of artificial intelligence.
He is Co-Founder of AI Trailblazers, a platform that brings together marketers, technologists, founders, and investors shaping the future of AI. Through Savvy Matters, he advises leading companies on marketing, AI, and business transformation.
Previously, Shiv served as Chief Marketing & Customer Experience Officer at LendingTree, where he led a high-performing team serving more than 100 million consumers and oversaw an annual media investment of approximately $700 million.
His expertise spans brand strategy, customer experience, and AI-driven transformation, with a focus on how emerging technologies are reshaping decision-making, growth, and competitive advantage. His current work also includes doctoral research on how agentic AI is redefining human expertise, identity, and accountability in the workplace.
Shiv serves on the board of United Rentals and is a Board Leadership Fellow at the National Association of Corporate Directors, as well as a member of the Nasdaq Center for Board Excellence.
He is the author of Marketing with AI For Dummies and two additional books, and has been recognized by Forbes, Adweek, Ad Age, and Business Insider, and inducted into the American Advertising Federation Hall of Achievement for his contributions to marketing and innovation.
Ben De Castro
Partner, Savvy Matters
Ben De Castro is a Partner at Savvy Matters and a marketing executive with more than 25 years of experience building brands and driving growth for both global corporations and high-growth innovators. His work centers on creating brands that earn trust, scale efficiently, and compete effectively in dynamic markets.
He is also a leading voice at AI Trailblazers, where he explores how artificial intelligence can amplify creativity, transform customer experiences, and unlock new sources of brand value.
Ben has held senior marketing leadership roles across a range of industries, including ING DIRECT, Bell Mobility, Gardyn AI, Mixbook, Eargo, Rakuten Kobo, Toronto Star Digital, and Finastra.
He is known for leading global rebrands, launching category-defining products, and helping position companies for IPOs and major retail expansion. His experience spans both established enterprises and emerging companies, giving him a practical perspective on scaling brands at different stages of growth.
His expertise includes full-funnel growth, lifecycle engagement, and brand architecture, with a consistent track record of accelerating revenue and strengthening market position. He brings a particular focus to how marketing strategy and execution evolve alongside changing consumer expectations and technology shifts.
Track Record
Growth, IPOs, and global brands
Across multiple industries, we've delivered results at the highest levels.
