AI isn’t a future conversation anymore. It’s already transforming how teams work, how decisions are made, and how quickly things can go sideways if no one is paying attention.
Level Up: Out of Office – The AI Leadership Series is a new monthly, in-person series designed for leaders who want to understand what AI actually means for their organization, without the hype or fear-mongering.
The kickoff virtual session will set the stage for a series of honest, practical conversations about AI, leadership, and what’s coming next. The series rotates through great local venues, bringing business leaders out of the office for discussions that go beyond tools and dive into strategy, risk, and real-world applications.
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What to Expect in the Kickoff Session
In this first session, attendees will explore:
- Where AI is creating real opportunity and where it’s quietly introducing risk.
- Why many organizations jump straight to tools before getting clear on strategy.
- How leadership expectations around AI, security, and governance are evolving.
- What leaders should focus on this year – and what they can safely ignore.
The session will also officially announce a partnership with Optiv, a company helping organizations of all sizes adopt AI and technology securely and responsibly, emphasizing risk, governance, and long-term resilience. Their expertise ensures these conversations stay grounded in reality, not just possibility.
Meet the Speakers
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Alex Aneroussos
Cyber Security Advisor | Results-Driven Account Executive | Championing Customer Success and Building Lasting Strategic Relationships
Alex brings a wealth of experience in cybersecurity and account leadership, helping organizations adopt technology safely while building lasting, strategic relationships. With a focus on results and customer success, Alex ensures AI adoption aligns with both business goals and secure practices.
John Weatherbie
Client Solutions Advisor at Optiv
John is a seasoned security advisor specializing in vulnerability and threat management, information security, and secure technology implementation. At Optiv, he helps organizations adopt emerging technologies like AI while reducing risk and strengthening their overall security posture.
Hosted by Rob Cupello
AI Strategist & Marketing Advisor
With over 20 years of experience leading marketing strategy and running a successful agency, Rob Cupello helps businesses navigate complexity with clarity and intention. Working at the intersection of AI strategy, smart marketing, and business alignment, Rob focuses on practical solutions that help organizations save time, reduce friction, and build brands that actually convert.
What’s Next
The kickoff session will also preview upcoming in-person Out of Office events, where the series will go deeper through curated gatherings, rotating venues, and practical examples, always leading with strategy first, not just tools.
If you’re looking to lead through AI thoughtfully, securely, and without pretending to have all the answers, this session is for you. Join business leaders in navigating the opportunities, risks, and decisions AI presents and take the next step in leading your organization into a future where AI is part of how work gets done.
Register here.
Passcode: 788713
