About WON.ai
WON.ai helps retail, travel, hospitality, and financial services brands transform operations and customer experience through AI native intelligence, strategic execution, and modern systems thinking.
Backed by leading investors and operators
Aglaé Ventures
Pari Passu Venture Partners
Centre Street Partners
Founderville VCThe Thesis
The companies that thrive in the next decade will not be the ones that bolt AI onto legacy structures. They will be the ones that redesign how work moves, how decisions are made, and how customers are served.
Consumers now expect anticipatory, intelligent, personal experiences across every surface. Most organizations are still optimizing yesterday's funnel.
Disconnected systems, siloed teams, and tactical AI experiments quietly compound friction, slow growth, and erode margin.
Customer experience and operational design are no longer separate disciplines. The future belongs to businesses that treat them as a single, connected fabric.
What WON.ai Is
We help retail, travel, hospitality, and financial services brands identify where intelligence, automation, operational redesign, and customer experience modernization can create meaningful business impact, then bring those initiatives to life.
The Practice
Division 01
Smarter, more effective customer experiences through AI assisted insight, experience strategy, design, optimization, and lifecycle thinking.
Division 02
Modernized workflows, operational visibility, automated inefficiencies, and intelligent operational systems built on AI.
The Layer Beneath
Customer insight, operational context, business goals, behavioral patterns, and market intelligence flow into a unified analytical fabric, then back out as decisions, automation, and orchestrated execution.
Inputs
Outputs
Philosophy
AI is a means. Business performance is the end.
Embedded intelligence outperforms isolated pilots.
How something works is inseparable from how it feels.
Built by people who have shipped, scaled, and operated.
We deliver. Strategy without launch is theater.
Every engagement ties to growth, margin, or leverage.
Where We Focus
We focus on industries where customer experience, operational efficiency, and digital systems directly influence growth and profitability.
The People
A small, deliberate team that has shipped consumer products, run operations, built brands, and integrated AI into real businesses. We work across functions because modern problems no longer respect them.
Dylan Whitman is the Founder and CEO of WON.ai. A serial entrepreneur, software executive, and active technology investor, he has spent more than 15 years building and scaling technology companies while helping organizations leverage AI, enterprise software, and digital commerce to accelerate growth, improve operations, and create competitive advantage.
Julia Connell is COO + Integrator at WON.ai, bringing more than two decades of leadership experience across ecommerce, SaaS, and consumer brands. Before joining WON.ai, she led digital commerce and operations for companies including NuFACE and Inveterate, where she specialized in scaling organizations, driving growth, and translating ambitious strategy into disciplined execution.
Kelsey Lancaster is VP of Design at WON.ai, leading the firm's Experience Intelligence practice. Her background spans enterprise SaaS, venture-backed commerce, and leading consumer brands, including GRIN, Thrive Causemetics, Thrive Market, and BVAccel. She specializes in designing AI-powered digital experiences that blend exceptional user experience with measurable business results.
Allyson Helms is Director of Delivery at WON.ai, bringing extensive experience building delivery organizations and operational systems for high-growth technology companies. Before joining WON.ai, she led cross-functional delivery and operations initiatives at Loop while partnering with enterprise organizations including Tesla, Google, GE, and McKinsey. She specializes in building scalable delivery models, aligning teams, and creating the operational systems that enable complex AI engagements to execute consistently at scale.
How we work
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WON.ai helps retail, travel, hospitality, and financial services brands rethink operations, customer experience, and business performance for the AI era.