Start the day with a relaxed networking opportunity over breakfast.

Kick off the event with a brief welcome from our president and co-founder, Jennifer DiPasquale, and get an overview of the day’s schedule.

For action-sport enthusiasts whose passion is their lifestyle, personalization is paramount to driving engagement and building loyalty.

Join Insider CMO Merve Nazlioglu and Nicole Roundy, World Champion adaptive snowboarder, two-time Paralympian, and Senior Marketing Operations Consultant at Tactics, to learn how the lifestyle retailer reaches its unique audience of skate and snowboarding enthusiasts.

Inspired by Nicole’s personal journey, we’ll reveal how Tactics leverages Insider’s AI-native platform to make marketers unstoppable in customer engagement. From creating personalized journeys across every channel their customers prefer to leveraging predictive, generative, and agentic AI to deliver relevance at the moments that matter most, this session shows how cutting-edge technology meets human-centered strategy.

As founder of The RealReal, Julie Wainwright built a billion-dollar brand that reshaped the luxury resale market and set a new standard for sustainability, trust, and innovation in retail. In this keynote, Julie shares the lessons she’s learned from leading a disruptive business — from navigating growth and change to staying relentlessly focused on the customer. She offers her perspective on the future of retail; the role of AI and technology in enhancing customer experiences; and why experiential, in-store moments remain essential in a digital-first world. Filled with practical insights and forward-looking strategies, this keynote will inspire you to embrace reinvention, innovation, and the power of putting customers at the center of everything you do.

Each year, Women in Retail Leadership Circle partners with a nonprofit that gives back to our community in some way. This year we are partnering with Susan G. Komen, the world’s leading breast cancer organization that addresses breast cancer on multiple fronts, including research, community health, global outreach and public policy initiatives in order to make the biggest impact against this disease.

By 2026, being AI-first won’t be a competitive advantage — it will be the baseline for every retail brand. In this fireside chat, Kelly Thacker and Zoe Meeran discuss what it takes to lead in this new era, cutting through the hype to reveal what “AI-first” really means in practice. They’ll explore three key shifts shaping the future of retail:

• Automate campaign creation and execution so marketing moves at the speed of the customer
• Deliver always-on, personalized customer support without adding headcount
• Turn data into a real-time decision engine that fuels growth and efficiency

Join Kelly and Zoe for a candid conversation that will leave you with clarity, urgency, and a roadmap for thriving in the AI-first world of retail.

Retailers are entering the 2025 holiday season facing uncertainty from evolving tariffs, rising costs, and unpredictable consumer behavior. This panel session brings together retail and brand leaders to share actionable strategies for navigating these challenges. Attendees will gain insights on anticipating consumer reactions, optimizing pricing and inventory, building supply chain resilience, and making data-driven decisions that protect margins while driving growth. Learn practical approaches to turn uncertainty into opportunity and position your business for success during the critical holiday season.

This interactive session is designed to help you spark a meaningful connection with a fellow attendee. Meet one person you’ve never met before for a five-minute conversation, using the question prompt displayed on the screen to guide your discussion. It’s a simple, engaging way to break the ice and start building relationships that can continue long after the event.

Take an extended break to connect with other attendees and reflect on the morning’s sessions.

What’s it like to be a part of the Women in Retail Leadership Circle? Hear directly from a member of this amazing community of women.

What would your life look like if you designed it around what fuels you instead of what depletes you? This talk empowers audiences to rethink time and energy as sacred resources. Through interactive reflection exercises and mindset shifts, attendees learn how to “make space” in their lives — for joy, purpose, growth and presence — by letting go of draining obligations and constant “shoulds.” Audience takeaways:

• Identify beliefs and patterns that prevent you from making time for what matters most.
• Reframe self-care and boundaries as leadership and performance tools.
• Learn a framework for weekly personal accountability toward purpose-driven activities.
• Walk away with a renewed sense of agency over your time, priorities and peace.

We’ll kick off this five-minute break with a group photo to capture the moment together. Afterward, take the opportunity to grow your network by scanning as many LinkedIn badges as you can. It’s a quick, fun way to make connections and create a lasting memory from the event.

Join us for lunch and roundtable discussions! Each table has a different topic related to some of the pain points you’re facing in the world of retail: Creating Customer-Centric Journeys; Innovating In-Store Experiences in the Digital Era; Leveraging Data Insights for Trust and Transformation; Embracing Next-Gen Payment Solutions

In this TED Talks-style segment, three retail leaders deliver powerful, 15-minute talks centered on leadership insights and inspiration.

• Meenakshi Lala on Exceeding Customer Expectations by Empowering Your Team;
• Victoria Lozano on Championing Creativity as a Leadership Imperative;
• Lori Singer on Leading Through Life’s Toughest Moments

What makes a physical retail experience truly resonate with guests? ChangeUp’s Experience Report analyzed over 200 brands, gathering data from thousands of consumers to reveal what they actually think about shopping today. In this session, Lynn Gonsior, chief operating officer at ChangeUp, will share key findings, including why some retailers create lasting loyalty, what common pitfalls are holding others back, and what drives repeat visits.

This interactive session is designed to help you spark a meaningful connection with a fellow attendee. Meet one person you’ve never met before for a five-minute conversation, using the question prompt displayed on the screen to guide your discussion. It’s a simple, engaging way to break the ice and start building relationships that can continue long after the event.

This session spotlights rising leaders who are driving change across retail — from accelerating innovation to shaping team culture and collaboration. We’ll explore how reverse mentoring and fresh approaches to leadership are fueling growth, agility, and connection in today’s fast-moving retail landscape. You’ll walk away with fresh leadership insights and actionable strategies to harness the power of rising talent—and to learn from them in the process.

Get ready for an unfiltered, energizing conversation with some of the most influential women of retail. This candid discussion goes beyond the highlight reel to explore what leadership really looks like — from bold career moves to navigating setbacks, managing high-performing teams, and staying grounded through it all. These powerhouse leaders will share the habits, mindset shifts, and sources of inspiration that fuel their success, including the books, podcasts and rituals that keep them going. Walk away with fresh perspectives, actionable advice, and a renewed sense of purpose. This is one session you’ll be talking about long after the event ends.

Thank you for joining us at our On the Road New York event! Our o-founder and president, Jennifer DiPasquale, sends us off.

An opportunity to unwind, network, and continue discussions in a more informal setting.