What is Flexera Live?

Flexera Live is a one-day, in-person event bringing together technology leaders to tackle rising costs across AI, SaaS and cloud.

As AI adoption grows, organizations are facing new challenges in visibility, accountability and cost control. This event focuses on how to understand the full economics of AI alongside the rest of your technology stack—and how to turn that insight into better decision-making.

Whether you’re a current Flexera customer, evaluating solutions or simply building and maturing your technology strategy, you’ll learn how leading teams are gaining visibility across their environments and building the control needed to manage spend with confidence.

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Why you should attend

  • Understand how AI is reshaping technology spend and why traditional cost models no longer hold
  • Gain visibility into AI, SaaS and cloud usage across your organization
  • Learn how to manage AI-driven consumption costs with greater control and accountability
  • Align IT, finance and engineering around smarter decision-making
  • Connect with peers navigating similar challenges in AI cost and governance
Arrival, registration and breakfast
Creating Clarity in the Era of Al, SaaS Sprawl, and Tech Accountability

As AI, SaaS, and consumption‑based models reshape technology spend, many organizations are struggling to clearly explain where money is going and what value it delivers. In this opening session, Flexera leadership will share how leading organizations are creating clarity, confidence, and accountability across complex environments — and how this shift enables better decisions, stronger governance, and sustained technology value.

Your Al Innovation Roadmap

In this session, you’ll see how Flexera’s latest innovations are already helping teams gain clearer visibility and accountability across ITAM and FinOps — as AI pushes organizations toward a 2026 tipping point for technology spend. You’ll explore why AI is about to dramatically increase IT budgets, what you can do about it, and get a first look at Flexera One’s AI‑native roadmap, including how you can ask questions across your entire technology ecosystem and get real answers instantly.

We’ll also look ahead to what’s coming over the next 6–12 months and how customer feedback is shaping what’s next — so you understand not just what’s changing, but how it will help you stay in control.

Real Life Wins: Turning Visibility into Value

Hear directly from Flexera customers navigating today’s evolving technology landscape. This panel explores how teams are using improved visibility to break down silos, adapt to AI‑driven change, and prove value in an era of increased scrutiny.

Discussion themes:

  • Managing AI and emerging technology spend without losing control
  • Breaking down silos between FinOps and ITAM
  • Proving value and accountability with executive stakeholders
Networking lunch
AI Value & Data Clouds: Managing the New Consumption Cost Curve (Snowflake, Databricks, and Beyond)

Data clouds and AI are shifting technology spend from predictable commitments to highly variable consumption, creating new challenges for visibility and accountability. This session looks at how FinOps and ITAM leaders are approaching the new consumption cost curve — and what capabilities are required to manage data, AI, and SaaS spend together.

FinOps + ITAM: One Operating Model for Technology Optimization

As technology spend expands beyond cloud into SaaS, AI, and consumption‑based models, traditional boundaries between FinOps and ITAM are breaking down. This session explores what a shared operating model for technology optimization looks like — and how organizations are aligning cost, risk, and value without creating new ownership gaps.

Why SaaS Pricing Has Entered Its Hybrid Era with Al

As SaaS shifts toward consumption‑based models and AI operates increasingly outside traditional applications, most organizations lack clear visibility into what software is being used, how it’s consumed, and where value is actually created. This session explores why visibility is breaking down today — and what that means for managing SaaS, cost, and accountability as AI reshapes how work gets done.

Who is Accountable for Al & Technology Value in 2026

As technology spend becomes more complex and harder to explain — driven by AI, consumption models, and fragmented ownership — many organizations are struggling to define who is truly accountable for value. This session explores how accountability for technology spend is shifting across FinOps, ITAM, Finance, and Engineering, and what leaders must do to create clarity, shared responsibility, and confidence moving into 2026.

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If you’re responsible for visibility, cost control, compliance or optimization, this event is built for you.

Speakers

Keith Hiszem

Senior Engineer, Server Software License and Compliance Management

Customer

Keith Hiszem
Senior Engineer, Server Software License and Compliance Management

Keith Hiszem is a Senior Engineer on the IT Asset Management Team at Cardinal Health. He spent several years in accounting before making the jump to IT. He started in IT as an application administrator before making his way to a FinOps team and eventually ITAM. Keith enjoys woodworking in his spare time and spending time with his wife and two boys.

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Mike Jerich

President & CEO

Flexera

Mike Jerich
President & CEO

Mike Jerich is the President and CEO of Flexera where he will execute the company’s ambitious vision to help organizations understand their technology spend and risk footprint, regardless of the type of technology, where it lives or who owns it. He has over 25 years of experience working in technology, overseeing complex software and cloud-native solutions across sectors.

He is a seasoned, results-driven leader who most recently served as Chief Executive Officer at HungerRush. Mike is known for his relentless focus on go-to-market strategy and execution, driving milestones across revenue growth, profitability, and customer retention.

Mike’s earlier roles include Chief Revenue Officer at ServiceMax (now PTC) and FinancialForce, Global Head of Sales and Marketing at IPC Systems, and Chief Commercial Officer at IntelePeer. He is a graduate of Stanford University.

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Steve Daheb

Chief Marketing Officer

Flexera

Steve Daheb
Chief Marketing Officer

Steve is responsible for global marketing, product marketing, demand generation and brand strategy. Prior to joining Flexera, Steve held CMO roles in tech companies including Uniphore, Tanium, Citrix, and ON24, for which he helped guide the company through its successful IPO, as well as SVP of Oracle Cloud Go-to-Market.

Steve is a recognized thought leader in branding, demand, and product marketing, and a frequent speaker and commentator in major business and financial media. He studied law at Santa Clara University and received his undergraduate degree at University of California, Davis.

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Troy Baker

Vice President, North American Sales

Flexera

Troy Baker
Vice President, North American Sales

Troy Baker serves as Vice President of North America Sales at Flexera, leading the company’s sales organization across the region. Since joining Flexera in May 2024, Troy has held multiple sales leadership roles focused on helping customers solve complex technology challenges and maximize the value of their IT investments.

Prior to Flexera, Troy spent four years at BMC Software in enterprise sales and sales leadership roles. He began his career at Accenture, where he spent four years in management consulting advising Fortune 500 organizations on strategic finance, procurement and business transformation.

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Roy Ritthaler

EVP - Customer Value

Flexera

Roy Ritthaler
EVP - Customer Value

Coming soon

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Guy Berenstien

Senior Solution Engineer

Flexera

Guy Berenstien
Senior Solution Engineer

Guy Berenstein is a Senior Solution Engineer at Flexera focused on FinOps, SaaS Management, and IT asset visibility for large enterprise organizations. He works at the intersection of go‑to‑market and product, helping translate customer needs into clear technical outcomes and product direction. As a member of Flexera’s FinOps pod, Guy helps educate GTM teams while ensuring product teams stay aligned with what customers need to be successful.

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Mark Bradley

Senior Product Management Manager

Flexera

Mark Bradley
Senior Product Management Manager

Mark Bradley is a Senior Product Management Manager at Flexera focused on Cloud Sustainability, IT Visibility - Sustainability, and Application Rationalization solutions. With nearly 25+ years of experience spanning product management, ITSM, ITAM, FinOps, and digital transformation, he has held leadership roles at Flexera, HP, HPE, Motorola Solutions, and JPMorgan Chase. Mark is a co-author of the AXELOS ITIL® 4 Leader: Digital & IT Strategy publication and is a frequent speaker on Cloud Sustainability, GreenOps, AI sustainability, and FinOps.

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Jeffrey West

Solutions Advisory Director, Data & Content

Flexera

Jeffrey West
Solutions Advisory Director, Data & Content

Jeffrey West is Solutions Advisory Director, Data & Content at Flexera. A former Flexera customer, Flexera Customer Advisory Board member, and technology leader at a global Financial Services company, he helps organizations use trusted technology data to improve IT Asset Management, reduce risk, optimize spend, support regulatory priorities, and drive measurable business outcomes. He holds certifications in FinOps and IT Asset Management, including FOCP, CAIAM, CITAM, and CSAM.

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Event details

Wednesday, September 23
9:30 a.m. – 5:00 p.m.

Guild Row
3130 N Rockwell St Chicago, IL 60618
Venue site   Map

5:30 p.m. – 9:30 p.m.
Evening event at Cubs rooftop

Nearby lodging

The Hotel at Midtown
2444 N Elston Ave, Chicago, IL 60647
Link

Hotel Zachary
3630 N Clark St, Chicago, IL 60613
Link

Best Western Plus Hawthorne Terrace
3434 N Broadway, Chicago, IL 60657
Link

Guild Row interior with seating
Guild Row patio seating
Guild Row meeting room

Guild Row is a modern, thoughtfully designed workspace and event venue in Chicago’s West Loop, featuring flexible meeting spaces, upscale finishes and a relaxed, social atmosphere ideal for team gatherings and offsites.

Join us after Flexera Live for an exciting evening experience from 5:30 p.m. - 9:30 p.m. CT

Every AI decision has a cost—and every cost needs visibility and control.

Join us in Chicago to learn how to manage AI spend with confidence, align teams around accountability and turn insight into meaningful business impact.

Complimentary for qualified end-user professionals. Space is limited to keep the experience focused and peer-driven.

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