Patrick O’Leary

Founder and CEO Boostr

Last Reviewed: September 18, 2026

Executive Summary

Patrick O’Leary is the founder and Chief Executive Officer of Boostr, a revenue platform built specifically for media and publishing companies. Boostr exists because of a problem he could not solve from the inside. Running sales operations at Yahoo!, O’Leary dealt continuously with poor pipeline visibility and inaccurate forecasts, and found that general-purpose CRM platforms could not fix them, because the underlying issue was that customer relationship management, order management and ad-serving data lived in separate systems with incompatible data models and duplicated master data. Rather than continue stitching those systems together, he left and built a single platform that combines CRM and order management for advertising sales. He founded Boostr in August 2015 after a career of more than 25 years in media and technology, including strategic planning and operations at Autodesk and consulting engagements at Siebel Systems.

Career Highlights

• Founded Boostr in August 2015 and has led it as Chief Executive Officer since.
• Built a unified CRM and order management system for media companies, eliminating the dual master data management and incompatible data models that come from running separate ad sales tools.
• Spent more than five years at Yahoo! in sales strategy and operations, leading sales operations and driving productivity and performance improvements.
• Led strategic planning and operations at Autodesk.
• Served as an Engagement Manager at Siebel Systems, one of the defining CRM companies of its era.
• Held earlier leadership positions at PCO Consulting, Inc. and IAS Systems.
• Recruited a Boostr leadership team from media, publishing and enterprise software backgrounds.

Professional Journey

O’Leary took a Bachelor of Science in systems engineering and management at the University of Virginia, a discipline concerned with how components fit together into a working whole, which turned out to be an apt training for the problem he would eventually build a company around. He held early leadership roles at IAS Systems and PCO Consulting, Inc., and then worked as an Engagement Manager at Siebel Systems during the period when Siebel defined what enterprise customer relationship management meant. He subsequently led strategic planning and operations at Autodesk.

At Yahoo! he spent more than five years in sales strategy and operations roles, ultimately leading sales operations, and drove a series of sales productivity and performance improvements. This was also where the frustration that became Boostr accumulated. Media advertising sales is operationally distinctive: an order is not a single transaction but a set of commitments about inventory, delivery and reconciliation over time, and the systems that manage the relationship, the order and the delivery are typically separate products. The result at Yahoo! was that pipeline visibility was unreliable and forecasts were inaccurate, and attempts to repair this with existing CRM platforms failed because the CRM could not see the order or the delivery.

O’Leary founded Boostr in August 2015 to address that directly, building CRM, order management and ad sales capability into one platform rather than integrating three. His argument for the approach is that integration is not a substitute for a common data model, and that a stitched-together stack will always reproduce the same reconciliation and master-data problems it was meant to solve. Boostr sells to media and publishing companies managing advertising sales, and he has built a leadership team drawn from both the media industry and enterprise software. He remains the company’s chief executive.

Education

University of Virginia

Bachelor of Science, Systems Engineering and Management