WTA + WI Tech Month Partner Event – The Future of Talent

Join us for this WI Tech Month partner event as we explore the Future of Talent in the age of AI.

2-4pm – Programming

This panel will tell the story on how their organizations are managing talent needs with the growth in AI for their team’s tasks, how they are upskilling or moving their team members into new positions and new responsibilities, and how they expect to see IT change as it comes to hiring and skills in the future.

4-6pm – Networking Happy Hour

As always, please stay to network with our speakers and fellow attendees over refreshments!

Moderator:

Casey, O’Brien, Director of Workforce, MKE Tech Hub Coalition,

Panelists:

Isaac Bennett, VP of IT at Stoughton Trailers

Kevin Alvara, Assistant Director of People Analytics and Data Science, Northwestern Mutual

Michelle Cass, Regional Head of Talent Acquisition, Prime Healthcare

Katie Grillaert, Co-Founder & Chief Strategy Officer, Assessed Intelligence

Casey O’Brien– Director of Workforce, MKE Tech Hub Coalition

Casey O’Brien is the newly appointed Director of Workforce at the MKE Tech Hub Coalition, where she is excited to lead initiatives to strengthen and retain the region’s technology talent pipeline. She previously served as Assistant Director at UW-Milwaukee’s Connected Systems Institute, where she developed online workforce trainings, including Digital Manufacturing Leadership and AI for Manufacturing, and launched industry-driven hackathons that connected students with real-world manufacturing challenges. An award-winning educator and Wisconsin Teaching Fellow, Casey dedicated more than 15 years to higher education as a senior lecturer, mentor, and faculty development innovator. She brings a strong commitment to inclusive, future-focused workforce development.

Outside of work, Casey enjoys collecting and listening to vintage vinyl records, teaching her young children to go analogue, and exploring the Midwest trails and lakefronts with her husband and their wily Australian Shepherd.

 

Isaac Bennett – Vice President of Information Technology, Stoughton Trailers

Isaac Bennett is an accomplished IT executive and digital transformation leader with over two decades of experience driving innovation across manufacturing and industrial sectors. As Vice President of Information Technology at Stoughton Trailers, Isaac leads strategic initiatives that align technology with business objectives, focusing on smart manufacturing, data integration, and operational efficiency.

Prior to joining Stoughton Trailers, Isaac held leadership roles at Tata Technologies, SAF-Holland, and Wright & McGill, where he spearheaded enterprise IT strategies, ERP modernization, and IT/OT convergence. His work has consistently empowered organizations to reduce downtime, improve throughput, and embrace Industry 4.0 technologies.

Isaac is a passionate advocate for leveraging data from sensors, actuators, SCADA, and MES systems to create intelligent, connected operations. He is also deeply committed to mentoring IT talent and fostering cross-functional collaboration to deliver scalable, secure, and user-centric solutions.

Outside of his corporate role, Isaac is actively involved in nonprofit work, including a mission to build a computer lab for a school in Ethiopia in honor of his late father, a former Peace Corps volunteer and educator.

Isaac regularly speaks on topics such as smart manufacturing, digital transformation, and IT strategy, and is known for his practical insights and visionary leadership.

 

Kevin Alvarado – Assistant Director for People Analytics and Data Science, Northwestern Mutual

Kevin Alvarado has built a robust career in data analytics and data science, currently serving as the Assistant Director for People Analytics and Data Science at Northwestern Mutual. In this role, they utilize data science models to evaluate employee sentiment and manage data migration to AWS. Previously, they worked at Molson Coors Beverage Company where he helped to led analytics for distributor networks, developed forecasting models, and automated reporting processes, significantly enhancing operational efficiency. His earlier roles at Northwestern Mutual involved leading behavioral analytics projects and creating predictive models for enterprise risk and cybersecurity. He has also developed various analytical tools and reports that supported business decision-making and strategy development. Prior to entering the corporate world, they completed an M.S. in Applied Economics from Marquette University and a B.S. in Economics from the University of the Pacific.

 

 

Michelle Cass, Regional Head of Talent Acquisition, Prime Healthcare
Michelle Cass is a seasoned talent acquisition and people strategy leader with over 20 years of experience helping Fortune 100 and high-growth organizations transform how they attract, engage, and retain talent. She currently serves as the Regional Head of Talent Acquisition for Prime Healthcare, where she built the entire talent function from the ground up following a major healthcare acquisition encompassing nine hospitals, 65 medical groups, and several senior living facilities. Throughout her career, Michelle has partnered with leading organizations such as GE, Ford, MetLife, Ericsson, Wells Fargo and Google, designing and implementing scalable, tech- enabled recruiting and workforce strategies that balance human connection with digital innovation. A Lean Six Sigma-certified change agent, she’s passionate about integrating analytics, AI, and automation into talent processes in ways that enhance; not replace the human element of hiring and employee experience. As the world of work rapidly evolves, Michelle brings a pragmatic and people-centered perspective on how AI will redefine recruiting, skills development, and organizational culture over the next five years. She believes the future of talent lies at the intersection of technology, empathy, and adaptability.

Katie Grillaert, Co-Founder & Chief Strategy Officer, Assessed Intelligence

Katie helps organizations turn AI risk into market-leading strategy. She is the Co-Founder and Chief Strategy Officer of Assessed Intelligence, a secure and responsible technology company specializing in AI applications in high-risk and highly regulated industries, and a ForHumanity Fellow and certified EU AI Act auditor. She leads strategy and partnerships that help organizations operationalize responsible AI, cybersecurity, and regulatory frameworks such as ARISE, NIST, ISO/IEC, and the EU AI Act. Katie’s work spans financial inclusion, biohealth, and critical infrastructure, with a focus on translating complex sociotechnical risks into actionable governance systems.