HDI Chicagoland Boat Cruise turned the Chicago River into a stage for a magnificent moonlit networking experience. Aboard the First Lady, guests sailed from river to lake, gliding past iconic landmarks. Spectacular views framed an evening rich with connection, fresh ideas, and lasting insights.
In our post-Covid industry, professionals are no longer satisfied with surface-level interactions—they crave authentic connection. Gartner reports that 85% of IT leaders seek deeper peer engagement, while Forrester reveals that 70% lack the relationships that spark innovation.
Chicagoland First Lady Cruise began as a networking event but transformed into an unforgettable journey through Chicago’s vibrant heart, glowing beneath the city lights at its most captivating hour.
As twilight deepened, the river shimmered with the fading blush of sunset. Warm hues shifted to the cool glow of night. The boat slipped beneath iconic bridges while the skyline began to sparkle, each lit window promising fresh ideas and bold possibilities.
Soon, we approached the Chicago Lock — an ingenious gateway between river and lake. Thomas Vick, of Robert Half told me of it’s fascinating function. For a moment, the city seemed to pause. The gates opened, the boat glided into open water, and a full moon rose over the horizon. Silver light danced on the waves, illuminating the faces of innovators, leaders, and changemakers immersed in lively conversation.
A Poetic Setting for Powerful Connections
Hosted by Chicagoland HDI, our President Daniel Guinto as Master of Ceremonies, and introduced the generously sponsored by Aisera – William Karges, Greta Varvell, Jess Emerick, and HappySignals, pride of Nashville’s Connor McCort the evening gathered service management professionals, technology innovators, and industry leaders in an environment that was equal parts Chicago charm and professional purpose.
Aisera took center stage with their groundbreaking Aisera Unify platform — the industry’s first multi-agent AI orchestration built on an open architecture. Their vision signaled the end of monolithic AI silos, ushering in a new era of seamless interoperability.
HappySignals inspired with their mission to help organizations shift from SLA-driven metrics to XLA (Experience Level Agreement) strategies, proving that human experience, not just technical resolution time, is the true measure of IT success.
Attendee Highlights & Industry Insights
Highlights of a few of the thought leaders present at this incredible event.
Silicon Valley’s own San Francisco Bay Area , Stephan Ng of Splashtop was a welcome friend from afar!!
- CIBC– Recently won the Best Gen-AI Initiative award in The Digital Banker’s 2025 Global Transaction Banking Innovation Awards. This recognition, for a second year in a row underscores the bank’s leadership in leveraging generative AI to enhance our client experience.
- Cognizant– No. 7 on CRN’s 2025 Solution Provider 500– Operates advanced delivery centers and innovation labs worldwide to co-create solutions with clients in areas like Generative AI, IoT, Automated Test, and data analytics.
- Blue Cross Blue Shield of Illinois – Offers deep insight into delivering enterprise-scale service within highly regulated industries where trust and consistency are paramount.
- Relativity – Strategies for scaling secure, high-performance service operations in competitive, compliance-driven environments.
- RKON (based in Chicago, founded in 1998) is an IT transformation and cybersecurity services provider that delivers strategic, scalable, and secure IT solutions tailored to both private equity and enterprise organizations.
- Robert Half – Discussed current staffing trends and the surging demand for multi-skilled IT professionals in Chicago, especially in AI, automation, and service leadership. Connects employers with top talent in finance, technology, marketing, legal, and administrative support roles.
- Splashtop is widely used for secure, high-speed remote desktop access and remote IT support, often as a cost-effective alternative to tools like TeamViewer or LogMeIn.
- TekSystems – Provided hiring intelligence showing resilient growth in cloud, data, and security roles across the Chicago tech market.
The Chicago Lock Story — A Lesson in Service Management
While approaching the Chicago Lock, I found myself in conversation with Thomas Vick of Robert Half. He explained to me the lock’s elegant brilliance:
Because the Chicago River sits lower than Lake Michigan in order move boats between them without flooding the city, the lock works like an elevator for water. First, gates close behind the boat. Then, water slowly fills or drains the chamber. Finally, when the water levels match, the opposite gates swing open. This precise, controlled process manages water flow and safeguards the city’s drinking supply from backflow.
Great service management works exactly the same way. You create a stable environment, balance all inputs, and open the gates only when conditions ensure a smooth, successful transition.
A Night That Will Be Remembered
Under the moon’s radiant glow, conversations flowed freely — about AI’s transformative potential, the measurable value of experience-led service, and the shared commitment to best practices. The harmony of Chicago’s architectural beauty and our united professional purpose reminded us that progress accelerates when visionary minds gather, share, and collaborate.
Your Invitation to the Next Chapter
If you missed this magical evening on the water, there is still time to step into the movement:
- Join HDI Chicagoland to connect with service and support leaders who are shaping the future.
- Explore Annual sponsorship or event opportunities with HDI Chicagoland’s Dawn C Simmons (VP Sponsorship) or HDI Chicagoland President Daniel Guinto, to align your brand with best practices, innovation and leadership.
- Network directly with professionals leading and participating in the best of Service Management and Support Operations practices to exchange insights and create lasting partnerships.
When we get involved, commit to best practices, and share openly, we elevate everything — together.
HDI Chicagoland Boat Cruise and More Information
- Annual Membership Benefits for Student and Professionals of HDI Local Chapters
- Brew City HDI – Milwaukee
- HDI Brew City | Events
- Bytes and Banter
- Corporate Sponsors Program
- HDI Chicagoland LinkedIn Group for Networking between meetings
- HDI Chicagoland | Events
- Industry News and views- SupportWorld – HDI
- Support and Service Management Training & Certification
- Webinars – HDI Library
HDI Chicagoland Boat Cruise and More events.
Board of HDI Chicagoland Local Chapter – HDI – Events – SupportWorld News – LinkedIn – Instagram