Union Square Advisors Research
Advisory Approach
Union Square Advisors operates with a distinctive thesis: technology companies need investment banking partners who deeply understand both technology and capital markets, led by senior professionals from the world's foremost technology practices who left large institutions to build something better. Founded in 2007 by Ted Smith (ex-Morgan Stanley, ex-Credit Suisse) and Carter McClelland (ex-BofA, ex-Deutsche Bank, ex-Morgan Stanley with 50+ years of Wall Street experience), the firm was built on two founding principles: create a platform where professionals genuinely understood technology, M&A, and capital markets; and attract individuals who highly valued teamwork and cooperation. This differentiation positions them as the "independent specialist" for technology companies—combining the expertise of Wall Street veterans with the agility of a focused boutique.
Union Square Advisors' strategic positioning emphasizes exclusivity and independence. Unlike full-service investment banks with competing business lines and conflicts of interest, USA focuses exclusively on M&A advisory and capital solutions. The firm has explicitly stated its commitment to "conflict-free advice of the highest integrity" and dedicates senior bankers to every engagement—no analyst-led deals. This positioning resonates particularly well with technology founders and companies seeking institutional-quality process without the overhead of larger banks.
Sector Focus & Specializations
Union Square Advisors has built deep expertise across multiple technology verticals, reflecting the breadth of the modern technology landscape:
Enterprise Software & Cloud Infrastructure: The firm's strongest vertical, with extensive experience in SaaS platforms, data infrastructure, cloud services, and enterprise applications. Recent work includes advising Riskonnect on the acquisition of Ventiv Technology (risk management RMIS platform) and Exiger on the acquisition of Versed AI (supply chain intelligence platform powered by AI/NLP).
Artificial Intelligence & Machine Learning: Given the current market focus, USA has positioned itself prominently in AI transactions. Recent deals highlight this: Versed AI (AI-powered supply chain visibility), Exiger (AI-driven risk management), and Scientist.com (AI-powered R&D orchestration platform in pharma tech). The firm's 2025 outlook emphasizes AI's transformative role across software segments.
Vertical Market Software (VMS): Particular strength in point solutions and industry-specific software serving healthcare, government, financial services, and specialized markets. The team's coverage of GRC (Governance, Risk, Compliance), Office of the CFO, and Back Office software serves mid-market companies and their financial sponsors.
Defense & Dual-Use Technology: Explicit focus on defense-related technology and commercial/dual-use applications, reflecting both national security importance and growing venture/PE investment in this space.
HealthTech & Life Sciences: Expertise in digital health platforms, pharma tech, and healthcare IT serving clinical, operational, and business intelligence needs.
Fintech & Financial Services Technology: Coverage of financial technology companies, including capital markets infrastructure, payment systems, and specialized financial services software.
Government Tech & Public Safety: Growing practice serving state and federal agencies, with expertise in government procurement, regulatory requirements, and public-sector technology buyers.
Deal Track Record & Transaction Profile
Union Square Advisors has completed 198 strategic transactions valued in excess of $125 billion since inception—an average deal value of over $600M per transaction, reflecting their focus on meaningful middle-market and larger opportunities. The firm's transaction history spans sell-side M&A, buy-side advisory, capital markets services (financing), and recapitalizations across publicly-traded and private companies.
Recent active deal flow includes:
- Exiger acquires Versed AI (July 2024): AI supply chain intelligence platform
- Riskonnect acquires Ventiv Technology (January 2024): Risk management software consolidation
- SS8 Networks sale to Mill Point Capital (June 2025): Lawful surveillance technology
- TPG invests majority stake in Conservice (January 2026): Property management software platform
- Scientist.com sale to GHO Capital Partners (September 2025): AI-powered R&D orchestration
- Grove Collaborative financing (January 2023): Consumer-direct CPG platform
- Permira acquires majority stake in Lytx (~$2.5B+): Telematics and fleet safety software
The deal mix reflects a balanced approach: sell-side transactions (founder exits, portfolio company sales), buy-side transactions (private equity and strategic acquisitions), and capital markets services (structured financings, refinancings). The firm explicitly covers venture capital, growth equity, and private equity sponsors—not just corporate clients.
Process, Team Structure & Advisory Philosophy
Union Square Advisors runs institutional-quality, senior-led processes with several distinctive elements:
Senior Leadership Model: Every engagement is led by a Partner or Managing Director. The firm explicitly rejects the analyst-driven model common at larger banks, ensuring client relationships are built with senior talent who have executed dozens or hundreds of previous transactions.
Team Composition: The firm has approximately 200+ professionals organized into practice groups: M&A (led by Wayne Kawarabayashi, Chief Operating Officer with 30+ years of technology M&A); Capital Solutions (led by Mike Meyer, CEO with 30+ years in structured finance); and vertical-specific teams (Software—led by Will Andereck, Jon Shalowitz, and Terry Jackson; HealthTech; Defense Tech; GovTech).
Process Rigor: Standard sell-side engagement structure includes valuation advisory, buyer identification and outreach, process management, negotiation support, and quality of earnings coordination. The firm emphasizes thoroughness in buyer development and process management rather than speed-to-market.
Independent Advice: Unlike diversified banks, Union Square Advisors provides advisory-only services. There is no principal investing, proprietary trading, or underwriting that could create conflicts. This positioning appeals particularly to founders and boards concerned about advisor alignment.
Technology Platforms & Buyer Relationships
Union Square Advisors' buyer network reflects decades of accumulated relationships across the technology ecosystem:
Private Equity Relationships: The firm explicitly covers Blackstone, KKR & Co., Apollo Global Management, Permira, Genstar, Audax, and hundreds of mid-market PE firms. Mike Meyer's role as Head of Capital Solutions and Todd Meadow's position as Head of Sponsor Coverage underscore the firm's commitment to PE sponsor relationships.
Strategic Buyers: Microsoft, Google, IBM, Oracle, Salesforce, and other large technology acquirers remain active buyers the firm advises on. Recent deals with strategic buyers (Riskonnect, Exiger) demonstrate ongoing strategic M&A activity.
Venture & Growth Capital: The firm has deep relationships with leading VCs and growth equity firms (General Atlantic, Hellman & Friedman, Siris, Vista).
Competitive Positioning & Differentiation
Union Square Advisors differentiates through:
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Founder-Built Independence: Founded by operators with successful track records (Ted Smith's experience at Novell as VP of Corporate Development; Wayne Kawarabayashi's 30+ years executing large transactions at Barclays/Lehman).
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Technology Depth: Led by people who understand the technology sector deeply—not generalists. The team's track record includes advising on transformational transactions for iconic companies (IBM, Microsoft, Oracle, Google, VMware, EMC, Informatica, SAP, Citrix, Nuance, Guidewire).
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Conflict-Free Model: Pure advisory focus eliminates conflicts inherent in universal banks with principal investing, proprietary trading, or other capital deployment.
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AI + Human Intelligence: Explicit positioning around leveraging AI capabilities alongside human judgment—reflected in recent hires (Gelila Bekele as Head of AI Strategy in 2026) and transaction coverage.
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Cultural Differentiation: Emphasis on teamwork, mentorship, and professional development. The firm explicitly highlights cases like Justin Best (analyst who competed in Paris 2024 Olympics while working at USA, winning gold) as evidence of their flexible, supportive culture.
Not a Fit For
Based on public positioning, Union Square Advisors typically declines:
- Companies seeking principal investment or quasi-equity arrangements
- Transactions requiring integrated banking services (underwriting, capital markets products)
- Companies below a certain minimum transaction size (implied $50M+ TEV minimum)
- Businesses outside the technology sector
- Clients requiring credit/debt services beyond advisory
Team Leadership & Expertise
Key team members bring world-class technology M&A experience:
Executive Leadership:
- Carter McClelland (Chairman, Co-Founder): 50+ years Wall Street experience; former President of BofA New York Market and Chairman of Banc of America Securities; former President and CEO of Deutsche Bank North America; 21 years at Morgan Stanley as CAO
- Ted Smith (President, Co-Founder): 30+ years executing transactions totaling tens of billions; former VP of Corporate Development and Business Development at Novell; ex-Credit Suisse (headed global software investment banking); ex-Morgan Stanley (early member of technology banking group)
- Mike Meyer (CEO, Head of Capital Solutions): 30+ years in leveraged finance; former Head of Global Credit at RBC Capital Markets; ran leveraged finance at Bank of America and Merrill Lynch; has executed 200B+ in capital solutions transactions
- Wayne Kawarabayashi (Chief Operating Officer, Head of M&A): 30+ years at Barclays and Lehman Brothers (since 1993) executing 200B+ in technology M&A; specialist in cross-border transactions and complex deal structures
Technology Practice Leaders:
- Will Andereck (Partner, Software): 15+ years in tech M&A; focus on MarTech, SalesTech, Contact Center, HCM markets
- Jon Shalowitz (Managing Director, Software): 30+ years Silicon Valley experience; CEO of 5 startups in Enterprise Software, each brought to successful exit; former product executive at 3Com, NetScreen/Juniper, CallidusCloud/SAP; MBA Stanford
- Terry Jackson (Managing Director, Software): 18+ years advising on 100B+ in transactions; leads vertical market software coverage; focus on payments, office of CFO, supply chain software; ex-JPMorgan, ex-BofA Securities; MBA Wharton, CFA, CPA
- Devon Ritch (Partner, M&A): 22+ years tech M&A experience; former Director at RBC Capital Markets; background in M&A law at Wilson Sonsini; JD/MBA Duke/Fuqua
Geographic Coverage
Union Square Advisors operates from two primary locations: San Francisco (headquarters, 1 Embarcadero Center, Suite 950) and New York (1350 Avenue of the Americas, Suite 700). The firm explicitly serves US-based technology companies and has UK representation through Sapia Partners LLP (FCA regulated). The San Francisco headquarters positions them centrally in the technology ecosystem; the New York office provides access to Fortune 500 clients and East Coast financial sponsors.
Historical Context & Performance
Founded in 2007, Union Square Advisors has now operated for 18 years through multiple technology cycles: the post-financial-crisis recovery, the mobile revolution, the cloud transformation, and the AI era. The founding team's decision to leave leadership roles at large banks reflects a specific thesis: that the best technology M&A advice comes from pure-play advisory boutiques where senior professionals own the client relationships and the outcomes matter directly to firm economics.
The firm's 2025 Outlook Report titled "Return to Momentum" predicts a significant increase in strategic and financing transactions, reflecting both macro conditions and structural tailwinds in technology M&A (AI acceleration, SaaS consolidation, cybersecurity M&A, government tech investment). The firm has explicitly positioned itself to capture upside from this expected recovery.
Strategic Value Proposition for Clients
Union Square Advisors' core value proposition to clients:
- Maximum Buyer Access: Senior relationships with 2,000+ active financial sponsors and strategic buyers built over decades
- Process Excellence: Institutional-grade sell-side and buy-side processes that maximize outcome for founders and boards
- Technology Expertise: Bankers who understand product, markets, competitive dynamics, and valuation drivers—not commoditized bankers
- Conflict-Free Advice: Pure advisory model ensures alignment with client interests
- Relationship Continuity: Senior bankers lead relationships from beginning to close, ensuring accountability and consistency
This positioning makes Union Square Advisors particularly attractive to: founder-led companies seeking to maximize exit value; private equity sponsors seeking sophisticated buy-side counsel; and technology CFOs and boards seeking M&A advice from experts with deep sector knowledge.