All Events & Webinars

Futures on the Road: Burlington, MA and Burlington, VT

Futures on the Road: Burlington, MA and Burlington, VT

Big Ideas. Local Conversations.

Two Burlingtons. Two dates. One agenda built for technology and business leaders.

Burlington, Massachusetts Wed, October 28, 2026 | 10 AM to 2:30 PM Microsoft, 5 Wayside Rd
[Register for Burlington, MA]

Burlington, Vermont Wed, November 4, 2026 | 2 PM to 6 PM Hula Lakeside, 50 Lakeside Ave
[Register for Burlington, VT]

ABOUT THE SERIES

The future of technology is being shaped right now by breakthroughs in AI, evolving cybersecurity threats, and new ways organizations create value through innovation. The most meaningful conversations don’t always happen on a conference stage.

That’s why we’re bringing Futures on the Road to a city near you.

Inspired by the most impactful sessions from our annual Futures Conference, this regional event series delivers thought-provoking content in a more intimate setting, creating opportunities for deeper discussion, one-on-one conversations, and meaningful connections with fellow technology and business leaders.

Whether you’re evaluating your AI strategy, preparing for emerging security threats, or looking to learn from peers navigating similar challenges, Futures on the Road offers a unique opportunity to engage, connect, and think differently about what’s next.

Same speakers. Same sessions. Pick the Burlington that fits your calendar.

CHOOSE YOUR EVENT

Burlington, MA

Wednesday, October 28, 2026 10:00 AM to 2:30 PM

Microsoft 5 Wayside Rd Burlington, MA 01803 [Get directions]

Daytime format with lunch and a Microsoft Innovation Tour to close the day.

[Register for Burlington, MA]

Burlington, VT

Wednesday, November 4, 2026 2:00 PM to 6:00 PM

Hula Lakeside 50 Lakeside Ave Burlington, VT 05401 [Get directions]

Afternoon format with a networking happy hour on the waterfront to close the day.

[Register for Burlington, VT]

WHO SHOULD ATTEND

This event is ideal for:

• CIOs and IT Executives
• CISOs and Security Leaders
• Infrastructure & Operations Leaders
• AI and Innovation Leaders
• Technology Decision Makers
• Business Leaders Interested in the Impact of AI
• Technology Professionals Looking to Stay Ahead of Emerging Trends

FEATURED DISCUSSIONS

Same three sessions at both locations.

How AI Would Break Into Your Company Tonight

Presented by Randy Becker

Artificial intelligence is rapidly changing the economics of cyberattacks. What once required weeks of planning, specialized skills, and significant resources can now be executed faster, cheaper, and increasingly autonomously.

In this session, Randy Becker walks through the anatomy of a modern AI-driven attack against an enterprise environment. From AI-powered reconnaissance and social engineering to voice cloning and credential compromise, attendees will gain a clearer understanding of how the threat landscape is evolving and what that means for security strategy moving forward.

The discussion also explores the growing security implications of copilots, agents, and autonomous systems, helping leaders understand where traditional security approaches need to evolve.

Key Takeaways:

• How AI is reducing the time and effort required to execute cyberattacks
• The emerging security risks surrounding AI agents and copilots
• What’s real versus what’s hype when it comes to AI-driven threats
• Strategic questions every technology leader should be asking now
• How to prepare their organization for the next generation of attacks

This session includes a live demonstration that illustrates how a modern attack can unfold without malware, stolen credentials, or traditional security alerts.

The Tokenomics Trap: Why Successful AI Projects Blow Up the Budget

Presented by Richard Amos

Most organizations are focused on what AI can do. Few are prepared for what AI will cost.

As enterprises move from pilots to production, AI economics shift from fixed costs to consumption-based costs driven by tokens, models, agents, orchestration, data processing, and infrastructure. What appears affordable with a handful of users can quickly become a major budget consideration at enterprise scale.

In this session, RIchard Amos demystifies AI economics and explores the hidden costs that often sit beneath successful AI initiatives. Through the lens of the “AI Cost Iceberg,” attendees will gain practical frameworks for understanding, forecasting, and governing AI investments before costs begin to outpace expectations.

Key Takeaways:

• Why AI is creating a fundamentally new technology cost model
• How token consumption impacts long-term AI spending
• The hidden cost multipliers behind AI workflows and agents
• Strategies for forecasting AI costs before scaling
• How to align AI investments with sustainable business outcomes

Everyone is talking about what AI can do. This session focuses on what AI actually costs and why understanding AI economics may be the difference between success and a budget overrun.

Put Your Agents to Work

Presented by Jeff Cratty

AI agents are ready to do more than assist. They are ready to execute. AI agents are moving from concept to execution, and organizations are starting to use them to reduce manual work, improve productivity, and accelerate everyday business processes. This session will explore how teams are identifying the right work for agents, applying governance and guardrails, and deploying agentic AI in ways that create real operational value. Attendees will hear practical examples of how agents can be put to work across the business, what it takes to build and manage them responsibly, and how to think about agent adoption as part of a broader AI readiness strategy.  

Key Takeaways:

Walk away with ideas for using agents to reduce toil, support teams, and improve business execution.

Understand where AI Agents can create practical value beyond traditional automation

Learn how to identify the workflows, tasks and operational pain points best suited for agents. 

Explore the governance, guardrails and readiness considerations needed to deploy agents responsibly.

AGENDA

Burlington, MA | October 28

Burlington, VT | November 4

WHY ATTEND

• Hear from industry experts on the topics that matter most, from AI and cybersecurity to strategy, governance, and innovation.
• In a smaller, regional setting, you’ll have the opportunity to engage directly with speakers and connect with local leaders facing many of the same challenges and opportunities.
• Walk away with new perspectives, actionable ideas, and strategic considerations you can apply within your own organization.

FAQ

Are these the same event? Same speakers and sessions, two locations. Attend whichever is closer or fits your schedule.

Which Burlington is which? Burlington, MA is October 28 at Microsoft, about 15 miles northwest of Boston. Burlington, VT is November 4 at Hula Lakeside on Lake Champlain. Registration is separate for each.

Can I attend both? Yes. Register for each separately.

Is there a cost? No, this event is completely free.

Stay Connected and Sign Up for Communications

Contact Us