Southfield Capital Acquires and Integrates AI Orchestration Platform Contextual.io to Enhance its Value Creation Abilities in The Lower Middle Market

AI-driven Full-Service Business Model Complements Firm's Technology Expertise and Business Services Focus, Furthering Ongoing Mission to Drive Value Transformation for Founders and Manager-Owners 

Contextual to Provide Customized AI Solutions for Small and Medium Sized Businesses

GREENWICH, Conn., Jan. 26, 2026 /PRNewswire/ - Southfield Capital ("Southfield" or the "Firm"), a premier lower middle market private equity firm, today announced that it has acquired Contextual.io ("Contextual" or the "Company"), a solutions-oriented AI orchestration platform that provides practical and actionable AI-driven value creation solutions to businesses across sectors. As part of the acquisition, Contextual's AI-driven capabilities will be fully embedded into Southfield's partnership model, facilitating the delivery of the Firm's ongoing mission to be a future-ready innovation and technology leading partner for founders and manager-owned businesses in the lower middle market. Terms of the transaction have not been disclosed.

Founded and led by CEO Andrew Brooks and the team that developed and successfully managed SmartThings through its acquisition by Samsung, Contextual is an AI solutions provider that rapidly deploys cost-effective, enterprise-grade AI solutions for any process, data, AI platform, business operating system, or industry. Working hand-in-hand with business leaders, Contextual's "Own your AI" mantra enables companies of all sizes to cost-effectively develop scalable AI solutions that provide meaningful competitive differentiation. The Company leverages a consultative sales approach to engage directly with businesses across sectors to identify areas ripe for AI solutions, facilitating the creation of fit-to-purpose work process automation that delivers immediate ROI and can open new lines of business or revenue. Contextual has an established track record of providing valuable cost reduction, increasing wallet share, and developing new service offerings across industries.

Since its founding in 2002, Southfield has partnered with exceptional founders and management teams to help transform businesses across the lower middle market. The integration of Contextual represents a natural next step in the Firm's commitment to scaling transformation by utilizing technology and shoulder-to-shoulder support to accelerate reporting and diligence structures, as well as drive operational excellence. Contextual's full-service business model, combined with Southfield's operational and financial expertise, allows for seamless integration of customized and practical AI-driven solutions specifically structured to identify new lines of revenue and meet the needs of each of its founder and manager-owned partners throughout the lifecycle of an investment. Additionally, Southfield will benefit from enhanced identification and vetting of new investment opportunities where AI-driven levers could have the most potential impact, helping to unlock growth opportunities across new sectors where operational excellence and automation can create a decisive competitive edge.

"Small and medium sized businesses have historically been under-served from a technology standpoint," said Bob Root, Transformation Partner at Southfield. "With Contextual, we can close this gap by providing a future-ready blueprint supported by a full-service business model that combines best-in-class business transformation expertise, technological acumen, cost-effectiveness, and speed and efficiency of execution. Throughout my more than two decades in functional technology implementation, Contextual's technological capabilities and deep understanding of business and market operations has stood out, and we have seen first-hand the impact these solutions and their partnership can have. The wholistic integration of Contextual into Southfield represents an important milestone in the ongoing evolution of our value creation model, marrying our on-the-ground, personal partnership approach with cutting edge AI solutions and infrastructure support built for company-specific applications across the duration of the business's lifecycle."

This latest step in Southfield's evolution follows the addition of Bob Root in 2023 to head the Firm's value creation efforts. The Contextual team adds to Southfield's unparalleled value transformation capabilities, adding the ability to develop and implement practical AI-driven solutions supported by a strong understanding of business operations. The formation of a highly-experienced senior team that combines investment acuity with deep technology and operational expertise, is part of Southfield's ongoing commitment to creating a diverse and specialized workforce designed to drive transformational value creation opportunities and directly lead the AI revolution for portfolio companies and LPs through a cutting-edge and innovative approach.

"Value creation has always served as the foundation for everything we do at Southfield, and we are strong proponents of the potential AI has to dramatically accelerate growth at each and every business," said Andy Levison, Founder & Managing Partner of Southfield. "Contextual complements our existing technology expertise, exceptional transformation leadership and shoulder-to-shoulder approach, which will re-align how we can meet and exceed the evolving needs of our founder and manager partners. We are excited to capitalize on this generational opportunity – for Contextual as it expands its breadth and market share, our portfolio companies as they partner closely with Andrew and his team, and for Southfield as we leverage these capabilities to enhance our processes and identify new avenues of growth potential."

"Southfield's get-it-done mindset, foundation in innovation and collegial culture rooted in collaboration, respect, authenticity, and transparency, aligns with our growth-focused mentality and core values at Contextual," said Andrew Brooks, CEO of Contextual. "We see a unique opportunity to help disrupt and bring meaningful efficiencies across the business services market, and Southfield's focus positions us well to quickly accelerate our growth. As an integrated part of the Southfield team, we are excited to bring technology and execution prowess to effectively utilize AI tools and evolve the value creation capabilities into an offering that is differentiated from all others in the lower-middle market."

About Southfield Capital
Southfield Capital is a premier private equity firm with a foundational commitment to driving value at high-growth, lower middle market companies in the business services sector. The firm leverages its deep team of highly-experienced investment, technology and value-creation professionals, combined with fully-integrated AI-driven capabilities to partner with founders and manager-owned teams of companies with $4-20 million in EBITDA. For more information, please visit www.southfieldcapital.com.

About Contextual.io
Contextual designs, builds, and operates purpose-built AI Solutions on a proprietary AI Orchestration platform designed for enterprise solutions -- not POCs. By combining a client's unique data and workflows with Contextual's pre-built tools and proven expertise in leveraging AI for true transformation, clients see production ROI impact in weeks, not months. For more information, please visit https://www.contextual.io/.

Investor Contact
Jason Perlroth
Principal, Head of Business Development, Southfield Capital
Email: [email protected]
Tel: 203 813 4117

Media Contact
Taylor Ingraham / Max Rayden
[email protected] / [email protected]
Tel: 203 992 1230

SOURCE Southfield Capital