Anu Gupta | B2B Online Chicago

B2B Online Chicago 2026

May 4 - 6, 2026

Chicago Marriott Downtown

Anu Gupta

Anu Gupta

Group Vice President eCommerce Tessco Technologies

Wednesday, May 6, 2026

1:20 PM Mastermind Roundtables & Key Takeaways

Mastermind Roundtables are a wonderful way to continue to network and engage with your peers on a topic of your choosing. Each roundtable will have a specific theme for you to learn from.

The Mastermind Roundtables at B2B Online are designed to foster intimate conversations around common hurdles. Come prepared to engage in small groups of 10-15 of your peers to discuss ways to re-strategize and overcome common roadblocks to success. This is an hour-long session. After the first 45 minutes, we’ll go around and hear what each table discussed.

1. Product Discovery & How Customers Are Finding Your Products -- Hosted by Nicole Alboushi - Sr. Director of eCommerce, Imperial Supplies

2. Search, discovery, and the shift from search engines to AI assistants – Hosted by Lisa Kowalkowski - Director Onsite Search, W.W. Grainger, Inc

3. Change Management – What Works and What Doesn’t When It Comes To Dealing With Change – Hosted by Michael Barber, CMO, StarTech.com

4. Getting Started W/ AI -> What you’re Doing, And How You’re Scaling – Hosted by Anu Gupta, Group VP, Tessco Technologies

5. Channel vs Marketplace: Navigating B2B Growth, Pricing Conflicts, and Go to Market Strategy – Hosted by Firat Ozkan, Chief Sales & Marketing Officer, Mount-It!

6. Leveling Up: Advancing Your Career To Be Your Companies Next Leader

7. Data Foundations That Actually Power AI and Personalization

8. Omnichannel Reality Check: Connecting Online and Offline Experiences

9. Amazon Marketplace: What’s Your New Ideas With Selling On This Marketplace?

10. B2B payments modernization: Net terms, embedded finance, and integration hurdles

2:20 PM B2B Online 2026 Group Therapy: Working Session to Process What We Learned (and What Still Feels Hard)

B2B eCommerce transformation is messy, overwhelming, and often feels harder back at the office than it sounds on stage. This facilitated, no-slides working session is designed as a group “therapy” moment for leaders to openly share what resonated, what felt unrealistic, and where they’re still stuck. Together, we’ll turn B2B Online 2026 insights into clarity and practical next steps.

  • Talk openly about what excited you—and what felt intimidating—throughout the conference.
  • Validate common challenges and frustrations by hearing from peers facing the same realities.
  • Unpack which ideas are truly actionable versus aspirational in your organization.
  • Pressure-test strategies, tech, and frameworks discussed during the event in a safe, peer-driven environment.
  • Co-create practical next steps you can realistically take in the next 30–90 days.
  • Leave feeling less alone, more confident, and clearer on how to move forward. 

Check out the incredible speaker line-up to see who will be joining Anu.

Download The Latest Agenda