Chicago
October 6, 2026
Le Méridien Chicago - Oakbrook Center
2100 Spring Rd, Oak Brook, IL 60523
Join the WaitlistThe decisions facing retail leaders aren’t getting any simpler. Customer expectations are shifting, growth is harder to unlock, and the playbook keeps being rewritten.
WIRLC: On the Road brings together executive leadership development and the real-world business challenges shaping retail today.
Through candid conversations with C-suite leaders, founders and industry innovators, thought-provoking panels, and valuable peer connections, you’ll gain fresh ideas and practical strategies for making smarter decisions, driving growth and leading through constant change.
At WIRLC: On the Road Chicago, we’ll have honest conversations about what it takes to build a brand, win customers and move a business forward when there’s no perfect playbook.
What Are the Big Themes We’ll Tackle?
* Turning AI into real business impact: Moving beyond experimentation and hype to identify where AI can create meaningful value.
* Prioritizing the biggest bets: How to decide where to invest your time, money and resources — and what to let go of.
* Using technology to better serve customers: How AI and innovation can help your business better understand, acquire and retain customers.
* Leading through what’s next: How to keep teams focused and moving forward when priorities, technology and customer expectations are constantly changing.
What Will You Take Back and Apply?
* Fresh ideas for uncovering growth opportunities and responding to changing customer expectations.
* Practical frameworks for prioritizing initiatives and making difficult tradeoffs.
* New ways to keep teams focused and aligned through uncertainty and change.
* Candid lessons from leaders about what worked, what didn’t and what they would do differently.
Speakers
Tuesday, October 6
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1:00 pm
1:30 pm
Registration and Networking
Arrive, check in, and connect with fellow attendees as the event begins.
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1:30 pm
1:40 pm
Welcome and Introductions
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.
Moderator
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Jennifer DiPasquale Co-Founder Women in Retail Leadership Circle
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1:40 pm
2:10 pm
From Mother’s Kitchen to National Brand: Lessons in Entrepreneurship, Leadership and Legacy
Building a national brand rarely happens according to plan. In this candid keynote, Monica Nassif, founder of Mrs. Meyer’s Clean Day will take us behind the scenes of the journey from a simple idea born in her mother’s kitchen to building Mrs. Meyer’s Clean Day into a nationally recognized brand. She’ll share the real decisions, risks, failures and unexpected turns along the way — including how she identified an opportunity, found her first customers, figured out what would resonate, and learned from what didn’t work. She’ll talk openly about the choices she made about where to invest, what to prioritize and, just as importantly, what to say no to. Through honest stories and hard-earned lessons, Monica will offer a real-world look at understanding customers, building a brand people care about, navigating growth and staying true to your purpose while evolving with the market.
Keynote
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Monica Nassif Founder and Former CEO Mrs. Meyer's Clean Day
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2:10 pm
2:20 pm
Meet Our Nonprofit of the Year
Each year, Women in Retail Leadership Circle partners with a nonprofit that gives back to our community in a meaningful way. Join us as we welcome this year’s nonprofit, the American Heart Association (AHA). The AHA is the nation’s oldest and largest voluntary organization dedicated to fighting heart disease and stroke.
Speaker
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Sarah Casalan Board Chair, Heart Challenge American Heart Association, Chicago
Moderator
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Julie Troyer National Senior Corporate Relations Lead American Heart Association
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2:20 pm
2:40 pm
Move, Mingle and Meet
This high-energy, facilitated networking activity is designed to spark authentic conversations and connections. Participants stand up, take a quick reset breath together, and walk around the room for about 30 seconds. When prompted to stop, attendees pair up or form small groups and respond to a fun or thought-provoking question. After three minutes of conversation, the process repeats with a new prompt and new connections.
Moderator
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Katie O'Malley Founder & Principal Coach (en)Courage Coaching
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2:40 pm
3:00 pm
Networking Break
Take an extended break to connect with other attendees.
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3:00 pm
3:05 pm
Member Moment
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.
Speakers
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Liz Allison CEO Tricoci Salon & Spa -
Susan Koger Senior Director, Membership Women in Retail Leadership Circle
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3:05 pm
3:15 pm
Finding Hidden Dollars: Creative Ways to Fund What’s Next
Join Jennifer DiPasquale, president of Women in Retail Leadership Circle, and Jenifer Hermann, chief marketing officer of Evergreen Trading, for a conversation about finding funds for what’s next. They’ll explore how retailers can unlock value from excess inventory, real estate and other overlooked assets to support new growth initiatives.
Speaker
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Jenifer Herrmann Chief Marketing Officer Evergreen Trading
Moderator
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Jennifer DiPasquale Co-Founder Women in Retail Leadership Circle
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3:15 pm
3:45 pm
Leading What Matters: Focus Influence and Results for Your Organization
In today’s fast-paced business environment, leaders are constantly navigating competing priorities, rising expectations, and limited time to focus on what truly drives impact. This keynote helps executives cut through the noise and focus on what matters most to create meaningful momentum for their teams and organizations.
Speaker
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Jennifer DiMotta Managing Partner and Founder Uprisors Growth Partners
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3:45 pm
4:30 pm
Top Challenges: A Collaborative Discussion
Join us for an engaging and interactive session where we will tackle the most pressing challenges facing retail leaders today. This collaborative forum will provide valuable insights, peer-to-peer learning, and practical takeaways as we explore solutions to the issues that matter most to you.
Speaker
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Stephanie Pugliese President and CEO Duluth Trading Co.
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4:30 pm
4:50 pm
Networking Break
Take an extended break to connect with other attendees.
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4:50 pm
5:30 pm
Leading With Impact: Real Stories, Tough Decisions and Lessons LearnedJoin an engaging conversation with senior women leaders as they share candid stories about the decisions, challenges and turning points that have shaped their careers and businesses. From navigating uncertainty to failures, pivots and lessons learned, this session offers a practical look at what it takes to lead through constant change. We’ll explore how leaders prioritize when everything feels important, where they’re using AI, how they’re developing talent, and the difficult decisions they’ve made — including what they’ve had to let go of and what didn’t work.
Speakers
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Roxanne Weng Chief Supply Chain Officer Dollar Tree -
Kim Lefko Chief Marketing Officer Ace Hardware -
Karen Daoust Executive Vice President, Sephora, Footwear & Accessories Kohl's -
Kim Lewis CEO and Co-Founder Listener Brands
Moderator
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Caroline Lombardi Partner, Global Hospitality and Leisure Practice Egon Zehnder
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5:30 pm
6:30 pm
Reception/Networking
An opportunity to unwind, network, and continue discussions in a more informal setting.
Partners
Supporting Partners
