Chicago (Downtown), IL
Next Meeting
RESERVE A SPOT
Date:
Wednesday March 18, 2026 5:30pm - 7:00pm America/Chicago
Location:
Zoom
Agenda:

Title: The PE Playbook: CFOs Driving SaaS Success Under Pressure.  
 

DATE: March 18th

TIME: 5:30pm-6:30pm CT

PE involvement in a portfolio is characterized by a focus on operational efficiency, margin expansion, and structured, data-driven growth strategies aimed at maximizing value for a lucrative exit within a typical 3 to 5-year horizon. 

Join us for an insightful discussion on how CFOs can lead SaaS investment in their organizations through accelerated growth expectations and Private Equity oversight. This session will feature Greg Leos, General Manager and Head of Payments at Weave. Greg brings more than two decades of executive leadership experience across Fintech, SaaS, cybersecurity, and global payments, along with a strong track record of guiding PE backed companies through complex revenue, operational, and market transformation initiatives as well as several company exits.

CFOs will gain practical lessons drawn from real front-line experience, including how to navigate high stakes expectations, scale efficiently, and drive measurable enterprise value while helping to create a culture of performance that achieves an ideal outcome. Greg’s background leading global revenue organizations, advising high growth early-stage technology companies, and contributing to successful exits will provide attendees with a clear, actionable perspective on what it takes to excel in a PE driven SaaS environment.


Gregory Leos is the General Manager and Head of Payments for Weave (NYSE: WEAV).  In this executive role, he leads all aspects of the payments business inside of this SaaS technology firm which serves the Healthcare segment.  Prior to Weave, he was Chief Revenue Officer for VikingCloud (https://www.vikingcloud.com/), a global leader in Cybersecurity and Payments Compliance.  In this role, he led all revenue efforts for this Private Equity-backed company including direct sales, indirect/channel sales, inside sales, SME and Enterprise.  His sales organization consisted of 150+ people across 5 continents. 

Prior to VikingCloud, Mr. Leos was a senior sales executive for over six years with Fiserv (NYSE: FI), a global provider of financial technology services and payments solutions.  Mr. Leos led the company’s vertical Enterprise sales team in addition to its Franchise Solutions business unit. In addition, Mr. Leos also held the role of the Business Banking Executive for Fiserv’s Joint Venture with Bank of America. 

Prior to his tenure with Fiserv, Mr. Leos spent over 20 years in senior sales roles with a variety of Fintech and Cybersecurity companies. Mr. Leos served as General Manager, Head of North America for Worldline (previously GlobalCollect), a global cross-border eCommerce payments company based in Europe.  In his General Manager role, Mr. Leos was responsible for all aspects of the company's business in North America.  He had full revenue (both new and existing) and P&L responsibility in addition to all other functional areas of the company’s business in North America.   In addition, Mr. Leos held senior leadership roles for cybersecurity firms Trustwave and Sysnet.

Mr. Leos has been an active part of the Cybersecurity and Fintech/Payments community for many years.  He has served on various advisory committees with the Electronic Transaction Association and Merchant Risk Council as well as participated in speaking engagements at a wide variety of industry conferences including the PCI Security Standards conference, the Europe MasterCard Risk Forum and the ETA Transact show. In 2018 and 2019, Mr. Leos was twice welcomed to Capitol Hill to meet with government officials and members of Congress regarding issues pertaining to the Fintech industry. Over the course of his career, he has participated in two successful company exits (GlobalCollect/Ingenico - $1.2B and Trustwave/Singtel - $810MM) and one IPO (Global Payments - NYSE: GPN). He is also actively involved in the startup technology community in Chicago, having recently joined the early-stage Venture Capital company Propellant Ventures as both an advisor and an investor. He also is an advisor to several startups including Aeropay, Aleeop and Yeeld.

In addition to his professional endeavors, Mr. Leos is active in community involvement and philanthropy.  He is currently a member of the Board of Trustees for Chicago’s Lincoln Park Zoo and for many years was on the board for Rainbows, a global children’s advocacy group. He was elected chairperson of the board in 2011.  In 2018, he was a guest speaker for the American Cancer Society at their annual Taste of Hope fundraising event and has been an ambassador for the organization since 2017.  And in 2019, Mr. Leos and his wife Kristin were named by the Chicago Family Health Center as recipients of the Craig and Susan Manske Award, given each year to individuals who have been noteworthy supporters of the organization.

Mr. Leos received a B.A. in Psychology from California State University-San Bernardino. He currently resides in Chicago.

Meetings

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RSVP Subject
Date / Time
Attendees Status Suggested Donation  
Reserve A Spot PE Playbook: CFOs Driving SaaS Success Under Pressure. Mar 18
5:30pm - 7:00pm America/Chicago
3 Not registered Free
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Chapter Description

Chicago Chapter is meeting on zoom monthly - usually the second Tuesday of the month at 5 PM or 5:30 PM Central time - look out for the meeting announcements sent to all Chicago Chapter members

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