Steven Cox on Building High-Performing Teams and Transforming Customer Experiences with AI-Driven Leadership

Bossing It: Steven Cox on Leadership, Team Building, and AI-Driven Customer Experiences

Steven Cox, CEO of Ryff, is focused on transforming how customers discover products online through generative artificial intelligence (AI) and computer vision (CV) powered machine learning. His team is scaling an innovative ad product that dynamically inserts relevant products into video streaming content in real-time, creating personalized and immersive experiences via Virtual Product Placement (VPP).

With over 20 years in technology and ecommerce product development, Steven brings deep expertise in customer-centric, data-driven solutions that boost growth, engagement, and loyalty across omni-channel environments. His background spans online search, personalization, advertising, merchandising, and technology management.

First Leadership Experiences

Steven’s introduction to leadership began in high school sports, where he saw firsthand how aligned teams can exceed expectations. Professionally, his leadership path started early at Microsoft, where he led operations for their largest product shortly after finishing his undergraduate degree.

Defining His Leadership Style

Learning from both effective and failed leaders helped Steven shape what kind of leader he wanted to be. He aims to develop his team’s potential without relying on heavy-handed or dictatorial methods.

Biggest Leadership Lessons

As his organizations grew, Steven realized he could no longer rely on deep subject matter expertise alone. Leadership effectiveness shifted to how well he communicated, listened, and influenced through others across a broad group. Setting up strong communication mechanisms became key.

The Path to Leadership

Steven never set out explicitly to become a leader but recognized that solving complex problems was best achieved in leadership roles. Confidence grew as his teams delivered increasingly complex products. His satisfaction now lies in seeing team members grow and evolve.

Leadership: Nature vs. Nurture

Steven believes leadership is a skill to be learned, not an innate personality trait. While charisma helps gain initial trust, maintaining that trust requires continuous effort, self-improvement, and providing growth and support to the team.

Challenging Aspects of Leadership

Providing honest feedback when a person or team has tried their best but hasn’t met goals is the toughest part for Steven. Sometimes, difficult decisions must be made to reallocate resources, reinforcing that success is based on merit.

Experiencing Failure in Leadership

Steven recalls a time when his entire team was laid off due to a business relocation decision made by higher management. He views this as a failure to effectively advocate for his team’s value and to build strong executive relationships that could have influenced outcomes.

Openness and Authenticity in Leadership

Authenticity doesn’t mean sharing everything. Steven emphasizes balancing transparency with the need to protect sensitive information due to legal or business reasons. Teams appreciate honest communication about direction and challenges without being burdened by unnecessary details.

Mentorship and Paying It Forward

Though Steven never had a formal mentor, he built close relationships with leaders he admired and learned from them. He offers similar support to others by providing access and opportunities to anyone who reaches out.

Leading Through Uncertainty

As CEO of a startup, Steven faces constant uncertainty and avoids making long-term promises. He leads by openly sharing challenges and plans with his team. Transparency about potential pivots helps maintain trust and stability despite market unpredictability.

Prioritizing Diversity and Inclusion

Diversity starts with recruitment—bringing in talent that reflects the customer base. Equally important is fostering a culture where all voices are heard and encouraged to contribute. Leadership sets and models these expectations consistently.

Maintaining Company Culture Remotely

Culture defines a company’s success. Ryff shifted to fully remote work across three continents, offering flexibility to meet goals. To keep everyone aligned, Steven relies on constant communication through video, calls, emails, and chats, ensuring the team stays connected as if working side by side.

Top Resources for Leadership Growth

Steven finds the best leadership lessons come from engaging with people—learning what works and what doesn’t from other leaders and team members alike. While books and formal resources help, real-world interaction remains his top teacher.

For product developers interested in integrating AI into their workflows or improving team leadership skills, exploring targeted AI courses can provide practical tools and insights. Resources like Complete AI Training offer tailored learning paths to stay current in AI-driven product development.