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

January 26, 2026

Share this article

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, CT — January 26, 2026 — 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 www.contextual.io.


Investor Contact

Jason Perlroth
Principal, Head of Business Development, Southfield Capital
Email:
jperlroth@southfieldcapital.com
Tel: 203 813 4117


Media Contact

Taylor Ingraham / Max Rayden
Email:
tingraham@ascadvisors.com / mrayden@ascadvisors.com
Tel: 203 992 1230


 

Recent Posts


Snow-capped mountain peaks under a pink and blue sunset sky, with dark rocky terrain in the foreground.
January 7, 2026
GREENWICH, CT – Southfield Capital, a premier lower middle market private equity firm, announced today that Kelvin Group, (“Kelvin”), a leading national provider of industrial and commercial mission-critical mechanical refrigeration services, process safety management and environmental compliance, has completed the acquisition of PermaCold Engineering, Inc. (“PermaCold”), a premier industrial refrigeration company headquartered in the Pacific Northwest. The acquisition of PermaCold represents Kelvin’s fourteenth acquisition since partnering with Southfield. Founded more than 30 years ago by industry pioneers, Steve Jackson and Randy Cieloha, PermaCold has built a reputation for excellence, innovation and reliability in the industrial refrigeration industry. The company is widely recognized for its expertise in ammonia and CO2 refrigeration systems as well as its ability to deliver complex, high-performance solutions to clients across the western United States. The integration of PermaCold into Kelvin Group's family of companies, which features reputable brands such as ARC Mechanical, Refrigeration Design & Service (RD&S), RC&E, HCG Associates, and JS Compliance, further solidifies Kelvin's standing as a national provider of mission-critical mechanical services. “Kelvin’s acquisition of PermaCold represents an exciting milestone as the company continues its national expansion strategy by entering the Pacific Northwest. PermaCold’s deep technical expertise, admired technician team and customer service focus makes them a natural partner for Kelvin,” said Harry Gray, CEO of Kelvin Group. “Together, we look forward to offering an enhanced set of capabilities to support our combined customer base.” “When we decided to sell, Randy and I were adamant in locating an organization that shares our company’s culture and values relating to customers and employees, and Kelvin more than achieved this goal,” said Steve Jackson, “We’re excited to leverage Kelvin’s national footprint to better serve our customers while staying true to the values that have guided us for more than 30 years.” Southfield Partner, Chris Grambling, commented on the transaction, "We are delighted to welcome the PermaCold team to the Kelvin family. PermaCold has built a phenomenal reputation in the Pacific Northwest and their addition bolsters Kelvin’s geographic coverage, establishing Kelvin as a coast-to-coast mechanical services provider." Deerpath Capital Management and Crescent Capital provided debt financing. G2 Capital Advisors served as the buy-side advisor to Kelvin. Finn, Dixon & Herling provided legal counsel to Kelvin and Southfield Capital. About Kelvin Group Kelvin Group is a national leader in the field of industrial and commercial mission-critical mechanical services, process safety management and environmental compliance. Its turnkey solutions provide design/installation, service and planned maintenance and testing and compliance of world-class mechanical systems for leaders in the food and beverage, cold storage, pharmaceutical, educational, health care, and process industries. Once engaged with customers, Kelvin assists business owners achieve mandated health, safety, environmental and regulatory compliance standards. For more information, please visit www.kelvin.cool . About Southfield Capital Southfield Capital is a private equity firm that invests in high-growth, lower middle market companies in the business services sector. The firm targets companies with $4 - 20 million in EBITDA and partners with management to scale the business through a combination of organic and acquisition growth strategies. For more information, please visit www.southfieldcapital.com .
Snow-capped mountain range under a pink and purple sunset sky; lower slopes are dark and forested.
September 4, 2025
Milrose Consultants and Southfield Capital Announce the Strategic Acquisition of Borne Consulting
Snow-capped mountain peaks under a pink and blue sunset sky, with dark rocky terrain in the foreground.
August 20, 2025
GREENWICH, CT – Southfield Capital, a premier lower middle market private equity firm, announced today that Milrose Consultants (“Milrose”), a leading national provider of building code compliance, fulfillment, and consulting solutions, has completed the acquisition of ARC Private Provider Services, Inc. and Plans Runner, Inc., (collectively “ARC”). The acquisition of ARC represents Milrose’s thirteenth acquisition since partnering with Southfield, and first in the Florida market. ARC provides permitting and code compliance services, specializing in expediting the process for Florida customers through the state's Alternative Plans Review and Inspections Program. With a decade of experience, ARC has supported billions of dollars in public and private construction throughout Florida by providing expert plans review, permitting, and private provider services. The partnership with ARC will allow Milrose to expand its core permitting and special inspections services into the South Florida market. ARC’s strong regional footprint and longstanding relationships with building departments also enable Milrose to better serve national accounts operating in the region. Additionally, ARC introduces a complementary third-party review and inspection service, unique to Florida, that enhances Milrose’s ability to offer faster permitting approvals and fully integrated inspection packages on major projects. Ricardo Bermudez, President of ARC Private Provider Services, Inc., expressed his enthusiasm for the partnership, saying, "Partnering with Milrose Consultants opens the door to new opportunities to deliver value across a broader range of markets and deepen relationships throughout the Milrose Companies. We’re excited to merge our strengths to drive innovation in the industry across our permitting, Alternative Plans Review and Inspections Program offerings.” "We are excited to welcome Ricardo, Nate, and the very talented team at ARC into the Milrose family," said Dominic Maurillo, CEO of Milrose Consultants. “ARC’s deep expertise in Florida permitting, private provider inspections, and third-party plan review expands our capabilities and strengthens our ability to deliver end-to-end code compliance solutions for clients with complex projects in key regional markets. This acquisition reinforces our commitment to providing comprehensive, high-quality support throughout every stage of the construction process, while enhancing our local presence and responsiveness in South Florida.” Southfield Partner, Chris Grambling, commented on the transaction, “The addition of ARC to Milrose represents another milestone in our mission to expand Milrose’s geographic coverage and range of services as an end-to-end national provider of building compliance consulting. We are thrilled to collaborate with Ricardo, Nate, and their team as we deliver even greater value to our clients.” Wiggin and Dana LLP provided legal counsel and Monroe Capital provided financing to Milrose and Southfield Capital. About Milrose Consultants Milrose Consultants is the national leader in the field of building code consulting and municipal expediting with headquarters in New York City and offices nationwide. Customers rely on Milrose to provide end-to-end building compliance services that include permitting, code & zoning, regulatory filing, special inspections, façade inspections, due diligence & research, and other compliance solutions. Milrose provides high-end services across various large, growing industries, including commercial, multi-family residential, retail, industrial, healthcare, and academia. For more information, please visit www.milrose.com. About Southfield Capital Southfield Capital is a private equity firm that invests in high-growth, lower middle market companies in the business services sector. The firm targets companies with $4 - 20 million in EBITDA and partners with management to scale the business through a combination of organic and acquisition growth strategies. For more information, please visit www.southfieldcapital.com.
Snow-capped mountain range under a pink and blue sunset sky.
August 12, 2025
GREENWICH, CT – Southfield Capital, a premier lower middle market private equity firm, announced today that Milrose Consultants (“Milrose”), a leading national provider of building code compliance, fulfillment, and consulting solutions, has completed the acquisition of ARC Private Provider Services, Inc. and Plans Runn