Co-Founders Brendan Paulin and Andrew Millard Join UPSTACK Partner Michael Leonardi as Founders of New Advisory Services Division 

NEW YORK, October 9, 2025 – UPSTACK, the leading full-service technology brokerage, today announced the acquisition of Breakwater Cloud Advisors, a fast-growing customer experience (CX) consulting firm based in Vancouver, Wash. The acquisition strengthens UPSTACK’s advisory and execution expertise in the rapidly expanding AI-driven CX solutions market and introduces the next phase of the company’s CX + AI practice. 

Founded in October 2021 by Brendan Paulin and Andrew Millard, Breakwater helps midmarket and enterprise organizations design and deploy next-generation CX solutions. The firm brings deep expertise across contact center as a service (CCaaS), conversational AI, workforce and quality management, analytics, automation and related solutions, with a strong presence in financial services, healthcare and hospitality industries. In addition, the Breakwater team boasts a successful track record of working with longtime UPSTACK Partner and CX authority, Michael Leonardi, to deliver customer value across an expanding CX solutions portfolio.  

As part of the acquisition, Paulin and Millard will join UPSTACK, as will Breakwater’s Business Development Director, Star Toups. The trio will continue collaborating with Leonardi, as well as Adam Gottfried, UPSTACK’s Director of Advisory Services – CX Solutions, to drive UPSTACK’s CX + AI practice by leveraging their combined expertise in contact center modernization, AI-driven automation and enterprise customer experience transformation. 

“Breakwater and its founders are exceptional additions to UPSTACK’s expanding CX + AI capabilities,” said Christopher Trapp, Founder and CEO of UPSTACK. “Brendan and Andrew have built a results-oriented consultancy that complements our mission to help customers modernize their CX environments and harness AI for measurable business outcomes. Together, with Mike’s deep experience, innovative approach and track record of success, they’ll deliver a new level of value for our clients.” 

“This acquisition represents a doubling down on UPSTACK’s investment in CX and AI,” said Leonardi, who will lead the CX + AI practice. “Bringing together Breakwater’s expertise with UPSTACK’s proprietary technology and scale positions us to deliver powerful, data-driven results for clients.” 

As the Breakwater team transitions into the UPSTACK organization, they will continue to serve clients with their signature high-touch approach while benefiting from UPSTACK’s platform, vendor network and deep technical resources. 

“From the beginning, we built Breakwater to help clients move faster and make smarter CX investments,” said Paulin. “Joining UPSTACK lets us keep doing what we do best—help customers innovate—while gaining access to resources, data and operational scale that take our impact to the next level.” 

Paulin’s perspective reflects the shared enthusiasm among the founding team, who see this milestone as both a validation of their approach and a launchpad for future growth. 

“We’ve worked closely with UPSTACK’s CX leaders from day one and we’ve seen the culture and vision up close,” added Millard. “This move gives our clients expanded support and gives us a bigger platform to grow with them.” 

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About Breakwater Cloud Advisors 

Founded in 2021, Breakwater Cloud Advisors is a CX consultancy specializing in contact center modernization, automation and AI transformation. The firm works with midmarket and enterprise organizations to design, implement and optimize CX ecosystems that drive efficiency and engagement. Breakwater’s expertise spans CCaaS, AI, workforce management and analytics, helping clients streamline operations and deliver better customer experiences. For more information, visit: https://breakwatercloud.net/. 

About UPSTACK

UPSTACK is the leading full-service technology brokerage that empowers businesses to make smarter technology investments. Through a vendor-neutral approach, UPSTACK delivers expert advisory and execution services across the entire technology landscape—including data center colocation, cloud, connectivity, networking, cybersecurity, AI and more—at no additional cost to its clients. For more information, visit us at www.upstack.com.