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This week, Cascadia Capital welcomed its Class of 2026 First-Year Analysts to the firm. It is a moment we look forward to each year: a new group of talented young professionals joining our team, ready to learn the craft of investment banking and contribute to the work we do for our clients.

Cascadia has always believed that the strongest working relationships start early. That belief shapes how we bring on and develop new talent, and it reflects who we are as a firm: independent, collaborative, and committed to growing careers from the ground up.

We are proud to invest in the next generation of bankers, and we look forward to the energy, curiosity, and hard work this class will bring to Cascadia in the years ahead.

Welcome to Cascadia.

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This week, Cascadia Capital welcomed its Class of 2026 First-Year Analysts to the firm. It is a moment we look forward to each year: a new group of talented young professionals joining our team, ready to learn the craft of investment banking and contribute to the work we do for our clients.

Cascadia has always believed that the strongest working relationships start early. That belief shapes how we bring on and develop new talent, and it reflects who we are as a firm: independent, collaborative, and committed to growing careers from the ground up.

We are proud to invest in the next generation of bankers, and we look forward to the energy, curiosity, and hard work this class will bring to Cascadia in the years ahead.

Welcome to Cascadia.

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One of our favorite times of year is here.

We are thrilled to welcome our 2026 summer analysts to the Cascadia team. Over the summer, they will be jumping headfirst into real transactions, working alongside our deal teams, and getting a firsthand look at what makes Cascadia a different kind of investment bank.

At Cascadia, we genuinely invest in the folks who come through our doors, and we love watching them grow over the course of a summer. To our new summer analysts: we are glad you are here. We cannot wait to see what you bring to the team.

https://player.vimeo.com/video/1199567811?badge=0&autopause=0&player_id=0&app_id=58479
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Cascadia Capital, an investment bank serving middle-market clients globally, is pleased to announce that Tonkean (the "Company"), a leading AI-native intake and orchestration platform for enterprise internal service teams, has been acquired by Coupa, a portfolio company of Thoma Bravo and the leading cloud-native, agentic trade network for autonomous spend management.

Headquartered in Palo Alto, California and co-founded in 2015 by Sagi Eliyahu, Tonkean is recognized as the first-of-its-kind intake orchestration platform that helps enterprise teams across procurement, legal, and finance create process experiences that people actually follow. Through its 100% no-code workflow editor, library of preconfigured process templates, and 250+ native connectors, Tonkean has become the automation platform of choice for many innovative Fortune 500 companies. Tonkean was backed by leading venture investors, including Accel, Lightspeed, and Foundation Capital.

This strategic move accelerates Coupa's ambition to power proprietary, two-sided, autonomous workflow automation across its global network of more than 3,500 buyers and 10 million suppliers, integrating advanced multi-agent orchestration and Agent-to-Agent (A2A) coordination into the Coupa platform. Tonkean represents Coupa's fourth strategic acquisition, following Cirtuo, Scoutbee, and Rossum, in its vision to build the world's foremost agentic trade network.

"The acquisition of Tonkean is game-changing for Coupa and the market," said Leagh Turner, CEO of Coupa. "We couldn't be more excited to welcome Sagi and the Tonkean team to Coupa."

"We couldn't have created a more powerful combination in the market than joining forces with Coupa, unlocking tremendous value to customers far and wide," said Sagi Eliyahu, Co-Founder and CEO of Tonkean. "With our industrial-grade intake and orchestration now serving as the backbone for their industry-leading agentic trade network, we will seamlessly connect buyers, sellers, and agents in a unified way to deliver autonomous trade in a way that no other company can match."

"Advising Tonkean on its partnership with Coupa is a landmark M&A transaction for Cascadia's revamped technology investment banking group. We are thrilled to help deliver a great outcome for our client and advise on a highly strategic acquisition for Coupa. Tonkean + Coupa is one of the best tech M&A stories of 2026," said Jonathan Cantwell, Head of Technology Investment Banking at Cascadia Capital.

This transaction highlights Cascadia Capital's deep expertise in advising companies across enterprise software, AI, and workflow automation verticals and reflects the firm's ongoing commitment to delivering outstanding outcomes for its clients.

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Cascadia Capital, an investment bank serving middle-market clients globally, is pleased to announce that Vertical Raise (the “Company”), a leading provider of K-12 fundraising solutions, has been acquired by Arbiter, a portfolio company of Accel-KKR.

Headquartered in Coeur d’Alene, Idaho and founded in 2018 by Paul Landers, Vertical Raise is recognized for combining modern fundraising technology with hands-on project management to help schools run effective, high participation campaigns. Over the past five years, Vertical Raise has supported tens of thousands of teams and schools, delivering an average of 37% more per fundraiser through its best in class digital campaigns and the Funds Manager Pro platform.

This strategic move strengthens Arbiter's commitment to supporting schools, families, and communities by integrating high performance, technology enabled fundraising into its growing suite of solutions, which already includes registration, payments, scheduling, facilities, and website management.

"Fundraising is an essential part of youth sports and a natural extension of how Arbiter can further serve families and schools," said Kyle Ford, CEO of Arbiter. "By welcoming Vertical Raise into our organization, we can deliver even more tools and more coordinated support to schools, while maintaining continuity in the products and teams they trust today."

"Schools and teams need fundraising that's simple, secure, and proven," said Paul Landers, Founder and CEO of Vertical Raise. "Our combination of automated digital outreach, personalized pages, and enterprise grade controls through Funds Manager Pro helps programs raise more money in less time. Now as part of Arbiter and their network of schools, leagues and families, we are excited to help even more teams and programs thrive."

This transaction highlights Cascadia Capital’s deep expertise in advising companies across education, fundraising, and marketing software verticals and reflects the firm’s ongoing commitment to delivering outstanding outcomes for its clients.

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The industry in focus feature for the Winter 2026 quarterly newsletter explores the rapid rise of vertical software — industry-specific platforms that are deeply embedded in workflows, highly sticky, and increasingly enhanced by AI. These businesses are proving more defensible, more durable, and more valuable than generic software — and they are attracting a disproportionate share of investor interest and M&A activity.

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Cascadia Capital, an independent investment bank serving middle-market clients globally, today announced that Nathan Gordon has joined the firm as a Director in its Technology Investment Banking group. Mr. Gordon will be based in Los Angeles and spend significant time in Silicon Valley. He will focus on originating and executing M&A and capital-raising transactions for enterprise software and technology companies.

Mr. Gordon’s addition follows Cascadia’s recent announcement of Jonathan Cantwell as Head of Technology Investment Banking, marking another important step in the firm’s commitment to scaling its Technology practice and deepening its capabilities across key subsectors.

Mr. Gordon has over 20 years of experience as an investment banker, private equity investor, and entrepreneur. Most recently, he founded, scaled, and successfully exited an e-commerce business, providing him with first-hand operational expertise that complements his years of advising and investing in middle-market growth businesses. Earlier in his career, he was a senior banker at Houlihan Lokey, where he advised technology companies on M&A and financing transactions. Mr. Gordon earned a B.S. from the Marshall School of Business at the University of Southern California.

“Welcoming Nathan is another step in Cascadia’s strategy to build a world-class Technology practice,” said Michael Butler, Chairman & CEO of Cascadia Capital. “We are making meaningful investments in this area to serve clients across the country, and Nathan’s expertise as both an advisor and operator further strengthens our ability to guide growth companies through complex strategic decisions.”

“I’m excited to welcome Nathan, who I have known for over 20 years, as we build momentum in Cascadia’s Technology group,” said Jonathan Cantwell, Managing Director and Head of Technology Investment Banking. “This key strategic hire highlights the firm’s commitment to expanding our capabilities. As we grow the practice, my focus is on recruiting top-tier talent and driving our efforts to advise category leaders across the technology sector. Nathan’s unique mix of entrepreneurial and advisory experience is exactly the type of perspective we want on our team.”

“Cascadia’s investment in its Technology practice comes as software companies face a wave of consolidation and renewed investor interest,” added Mr. Gordon. “I’m excited to help grow the group’s presence and support entrepreneurs and investors as they navigate this next phase of the market."

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Strategic Hire Signals Launch of Silicon Valley Office Amid Expansion of Cascadia's Technology Practice

Cascadia Capital, an independent investment bank serving middle-market clients globally, is pleased to announce the appointment of Jonathan Cantwell as Head of Technology Investment Banking. This strategic hire underscores Cascadia’s commitment to scaling its Technology practice and formally launching a dedicated Silicon Valley office to serve innovative growth companies.

With more than 20 years of technology investment banking experience, Mr. Cantwell has completed over 100 transactions with public and private technology companies. He brings deep domain knowledge across enterprise software, including transaction experience with artificial intelligence (AI) companies. Over his career, Mr. Cantwell has closed deals with leading technology companies such as Oracle, Salesforce, IBM, Workday, UiPath, Vonage, and Mindbody, and with private equity firms including Vista Equity, Accel-KKR, Insight Partners, Spectrum Equity, PSG Growth, Marlin Equity, and K1, among many others.

Prior to joining Cascadia, Mr. Cantwell was a Partner and Head of the Software practice at GP Bullhound. He previously was a technology banker at Pacific Crest Securities and Pagemill Partners in Silicon Valley and began his career with Ernst & Young in New York. He holds a degree from the Marshall School of Business at the University of Southern California.

“Technology remains one of the most dynamic and opportunity-rich sectors in the global economy and it is currently at the beginning of a transformational wave with AI. Cascadia is committed to investing in the people and resources needed to serve the technology sector at the highest level,” said Michael Butler, Chairman & CEO of Cascadia Capital. “Over the past two decades, we’ve built deep expertise in high-growth industries, and bringing Jonathan on board reflects our strategy of identifying key sectors early and assembling best-in-class teams to help clients navigate pivotal moments in their growth.”

“Jonathan brings a rare combination of seasoned execution experience, deep software sector insight, and an exceptional global network,” Butler continued. “His track record in enterprise software and his ability to guide clients through complex transactions make him the ideal leader for Cascadia’s Technology Investment Banking practice. We are thrilled to welcome him and look forward to expanding our footprint in Silicon Valley and beyond under his leadership.”

Mr. Cantwell joins Cascadia as the firm establishes its Silicon Valley presence, the cornerstone of a plan to grow a team of approximately 20 technology bankers focused on the high end of the middle market. As head of the group, Mr. Cantwell will spearhead recruitment of top talent and drive the firm’s efforts to advise category leaders across the technology sector.

“Cascadia has a proven history of recognizing emerging trends and building sector-specialized teams to meet client needs, and I’m excited to lead and grow the Technology group,” said Mr. Cantwell. “The pace of innovation in enterprise software, particularly in enterprise automation and agentic AI, creates tremendous opportunities for strategic consolidation and growth investments. I look forward to partnering with our talented bankers to help clients capture those opportunities and build on Cascadia’s reputation as a premier advisor to the middle market."

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Nathan Gordon is a Director in Cascadia’s Technology practice, joining the firm in September 2025. Most recently, Nathan started, operated and successfully exited an E-Commerce business. His experience as an operator complements more than a decade spent advising, evaluating, and investing in middle-market businesses across a range of industries, where he developed expertise in transaction execution, financial analysis, and strategic growth initiatives.

Nathan graduated from the Marshall School of Business with a B.S. from The University of Southern California.

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Cascadia delivers independent analysis and objective insight to help stakeholders move forward with confidence.

👉 Explore our capabilities: https://lnkd.in/dQCk7rWf

https://vimeo.com/1112363622?share=copy#t=0
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Cascadia Capital, an independent investment bank serving middle market clients globally, is pleased to announce it acted as the exclusive financial advisor to Enlighten, a leading provider of workforce optimization software and professional services, in its Acquisition by ActiveOps plc (AIM: AOM), a global leader in Decision Intelligence software for service operations.

Founded in 2003 and headquartered in Sydney, Enlighten delivers operational excellence solutions to enterprise customers across North America and Asia Pacific, with a strong footprint in the financial services, insurance, and healthcare sectors. The combination of these businesses significantly expands ActiveOps’ presence in North America and Asia Pacific, while creating a powerful platform in workforce analytics and organizational transformation, with a strong opportunity for cross-selling and product integration across both customer bases. Enlighten’s Andrew Johansen will take on a leadership role within ActiveOps, supporting continued commercial growth in the North American and Australian markets.

“This transaction reflects the increasing strategic importance of workforce optimization and analytics in today’s enterprise software ecosystem,” said Teague Collins, Managing Director at Cascadia Capital. “Enlighten has built a differentiated platform with deep expertise in complex service operations, and ActiveOps is a natural fit to help accelerate their reach, scale, and innovation.”

“We truly valued Cascadia’s guidance and advocacy throughout this process,” said Brent Churchill, co-founder of Enlighten. “Their team brought deep sector expertise and unwavering commitment to achieving the right outcome—for our individual goals, our employees, and our customers.”

“We were honored to advise Brent, AJ and the Enlighten team on a highly competitive and global process,” added Hugh Campbell, Managing Director at Cascadia Capital. “We continue to see technology’s potential for optimizing services-based models as a defining attribute of our practice.”

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Cascadia Capital, an investment bank serving middle-market clients globally, is pleased to announce it acted as the exclusive financial advisor to Bouncie, a rapidly growing automotive SaaS solution, in its growth recapitalization by Nova Street Partners, LLC. The capital will be used to recapitalize the business by retiring preferred securities, refinancing existing debt, and funding key growth initiatives, positioning Bouncie to accelerate B2B customer acquisition, enhance product capabilities, and scale its platform.

Headquartered in Dallas, Texas, Bouncie provides an easy-to-install, plug-and-play GPS tracker that connects via a vehicle’s OBD port to deliver real-time location, trip history, driver behavior analytics, and vehicle diagnostics. Designed for both families and small to mid-sized businesses, the platform offers an intuitive mobile and web interface with tools for managing fuel efficiency, insurance, registration, and maintenance, making vehicle ownership simpler, safer, and more connected through an affordable monthly subscription.

“Bouncie is an impressive SaaS solution that operates at the forefront of the emerging connected vehicle space, supported by real-time data, analytics, and insights – technology sectors where Cascadia is building deep domain expertise,” said Muizz Kheraj, Managing Director at Cascadia Capital. “It was a privilege to work alongside the team at Bouncie to craft a strategy that supports the company’s vision and aligns with investors’ appetite in this space.”

“This transaction demonstrates Cascadia’s ability to deliver customized capital solutions that support our clients’ strategic objectives,” said Tom Mills, Managing Director and Head of Cascadia’s Capital Markets group. “In close partnership with our Software and Technology team, we crafted a flexible recapitalization that enables Bouncie to accelerate growth and execute on its long-term vision.”

Cascadia’s Technology and Capital Markets teams collaborated to deliver an expedited and successful recapitalization outcome. The transaction underscores Cascadia’s ability to bring together sector-specific insight and creative capital markets execution. Cascadia managed due diligence, structured the process, and negotiated a bespoke financing solution that supports Bouncie’s continued growth and strategic priorities.

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With the recent election outcome, the potential impacts on markets are top of mind for business owners, investors, and dealmakers across industries. While macroeconomic discussions often dominate the discourse, Cascadia Capital focuses on delivering insights that go beyond broad trends, tailored specifically to the sub-verticals we serve. Our industry experts recently discussed their opinions and perspectives on how the new administration’s policies could potentially shape various industry sub-sectors.

Below is a representative selection of insights from our sector bankers, offering a glimpse into how these anticipated changes have the potential to affect their respective areas of focus. This is not a comprehensive overview, but rather a snapshot of the key developments and trends we are monitoring closely and the changes we predict based on our experience and current understanding of the market.

To discuss how market changes may impact your business or investment strategies, please reach out to a team member that covers your industry in depth.

The Trump election could bring notable changes to healthcare policies and subsectors, potentially reshaping the industry's landscape. Some stakeholders view this as an opportunity for increased activity in healthcare mergers and acquisitions (M&A), particularly if the administration takes steps to reverse the Federal Trade Commission’s (FTC) more restrictive stance toward private equity in healthcare. Such policy adjustments might encourage investment and pave the way for greater consolidation and innovation, creating potential opportunities for growth and operational efficiencies. Additionally, a shift toward a more business-friendly regulatory environment may prompt private equity firms to explore emerging markets, such as digital health, physician practices, and value-based care models, which could gradually influence the broader healthcare ecosystem.

The recent uptick in the Purchasing Managers' Index (PMI) from a 15-month low of 47.3 in September to 48.5 in October has sparked interest, with some attributing this to pro-business optimism around Trump’s potential election win. While U.S. manufacturing remains in contraction, this data could possibly signal easing in the downturn, with November numbers offering more insight.

The tech industry anticipates a favorable shift under a Republican-led government, with relaxed regulations potentially easing some of the more stringent compliance standards on data use and privacy, particularly within digital advertising. This approach could create a ripple effect across various sectors reliant on advertising and data-driven insights.

As we navigate this evolving landscape, Cascadia remains committed to delivering relevant insights that help our clients anticipate and adapt to the full range of market dynamics and outcomes—whether it's policy shifts, changing economic conditions, or emerging industry trends.

We hope these insights, based on our current observations and predictions, will provide some perspective as you navigate the opportunities and challenges ahead. While the true outcomes remain uncertain, we aim to help you prepare for potential market shifts. To discuss how these possible changes may impact your business or investment strategies, please reach out to a team member that covers your industry


Disclaimer | This information is being furnished by Cascadia Capital, LLC (“Cascadia”) to the recipient and is intended as an outline of matters for informational and discussion purposes only. The information contained herein, including any market data and industry information, has been derived entirely from material supplied by public sources, which Cascadia believes to be accurate; however, no independent verification of such material has been made and any estimates made by Cascadia based on material from such sources are by their nature inherently inexact. Accordingly, Cascadia does not make any representation or warranty, nor is any such representation or warranty implied, as to the accuracy or completeness of the information contained herein, and Cascadia is not responsible for any misstatements or omissions in this summary. Cascadia has no obligation to update the information contained herein.

This presentation may include certain statements, estimates and projections with respect to a company, or industry, including certain forward-looking statements. Any such statements, estimates and projections reflect various assumptions, which may or may not prove to be accurate or correct, concerning anticipated results and are subject to significant business, economic and competitive uncertainties and contingencies, all of which are beyond the control of Cascadia. Accordingly, there can be no assurance that such statements, estimates and projections will be realized. Such statements, estimates and projections are likely to vary from actual results and those variations may be material. No such statements, estimates or projections constitute a guarantee, promise, forecast or prediction of the future and Cascadia does not represent or warrant that any estimates or projections will be achieved. Cascadia neither: (i) accepts responsibility for or makes representations as to the accuracy or completeness of any forward-looking statements, estimates or projections contained in this presentation, nor (ii) undertakes any obligation to update or revise any forward-looking statements, estimates or projections for any reason after the date of this presentation. All financial data in this presentation is provided for informational and discussion purposes only. Past performance is not necessarily indicative, or a guarantee, of future results. There can be no assurance that any Cascadia project will achieve comparable results as those presented herein.

The information contained in this summary is strictly confidential and may not be reproduced, distributed, disclosed or disseminated, in whole or in part, to any third party without the prior written consent of Cascadia.

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This week, Cascadia Capital welcomed its Class of 2026 First-Year Analysts to the firm. It is a moment we look forward to each year: a new group of talented young professionals joining our team, ready to learn the craft of investment banking and contribute to the work we do for our clients.

Cascadia has always believed that the strongest working relationships start early. That belief shapes how we bring on and develop new talent, and it reflects who we are as a firm: independent, collaborative, and committed to growing careers from the ground up.

We are proud to invest in the next generation of bankers, and we look forward to the energy, curiosity, and hard work this class will bring to Cascadia in the years ahead.

Welcome to Cascadia.

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