We are thrilled to announce that Contextual has joined the Southfield Capital family. This is a unique partnership and a clear demonstration of the role forward-looking Private Equity companies can take in driving innovation across their portfolios and the industry broadly. Before we jump into where we expect to take Contextual in the coming years as a key partner in the Southfield portfolio, we wanted to reflect on why this relationship made so much sense.

Aligned AI Vision

At Contextual, we believe that AI represents an entirely new resource for organizations seeking to transform, grow, and differentiate. Classically, organizations think about their resources as People, Process, and Systems. We would argue AI is NOT a part of Systems as it’s generally understood. It’s a new form of electricity that disruptive organizations can use to not only streamline automations, but fundamentally change how business is done.

At the most foundational level, this means we believe future industry leaders will be rethinking how their organization is structured, what processes exist and who is the ‘teammate’ responsible for that process (human, AI, hybrid?), and where investments in technology and systems should be made.

Bob Root, Transformation Partner at Southfield Capital, characterizes this succinctly. “We absolutely see opportunities within our portfolio for AI-driven automation, but we’re even more interested in the second and third order benefits that an AI-first organization can unlock. New business models. New services. New market opportunities. New insight. We’re early in the journey, but recognize this shift is foundational. It’s not a feature.”

Aligned Market Opportunity
(Own Your AI^TM)

At Contextual, we saw that the fundamental change presented by AI was going to be uniquely impactful for lower middle market businesses. These are companies that historically had to ‘make do’ with the technology capabilities and solutions that off-the-shelf SaaS products provided. Every company and competitor generally had the same ERP and CRM tools. But AI creates a dramatic new unlock because the barriers to purpose-built solutions - matched explicitly to the organization’s unique differentiation - fall away. Specifically:

1. AI is an accelerant to solution creation. The act of ‘building’ new software solutions - from automations to new human-AI interfaces to entirely new products - with AI tools (and to be clear, not vibe coding, but code acceleration) has gotten dramatically easier. We expose this as SolutionAI within our platform. It means the cost of creating intellectual property as a moat has gone down, and lower middle market companies can now capitalize on that value.
2. AI is a new ingredient - the electricity mentioned above - in those solutions. This capability serves new functional purposes with a simple prompt (reasoning, research, intelligence, analysis, discovery) that previously would have required endless lines of code if they were possible at all, meaning lower middle market companies couldn’t even dream of creating their own answers to the most pressing problems in their organization.

Combined, these realities are why we encourage our clients to think of this in terms of owning their AI. They don’t inherit features. They aren’t restricted to functionality that a third party defines. They can weave distinct, differentiated, and powerful AI solutions throughout their organization in the exact manner they need to win.

Southfield Capital shares the belief that success for lower middle market companies in the coming years is fully embracing this new opportunity. They are leaned in on the impact of AI as a transformation and enterprise value creation lever within their portfolio and funds.

Beyond the Portfolio

Ultimately, our opportunity to join the Southfield Capital family was interesting thanks to the aligned AI vision and consistent view of the market opportunity described above, but it became a no-brainer as we realized that Southfield shared our belief that we - at Contextual - could bring this market transformation to thousands of lower and mid-market companies across the globe. We didn’t enter into this transaction simply to be a utility within their organization. We all believe Contextual can be an industry-defining company for the AI era.

Within the defensible AI and IP moats we create for Southfield’s portfolio companies, there are a series of recurring patterns that we see again and again where AI can have an immediate impact. They include:

• High-Volume Knowledge Work - Manual, repetitive, or document-heavy processes persist because traditional software can’t handle the complexity - driving cost, backlog, and inconsistent quality. 
• Time-Critical Operations - Speed matters, but expert bottlenecks, slow handoffs, or delayed decisions quietly limit growth and execution.
• Enterprise Data Advantage - Valuable data exists across systems, but insight isn’t reaching decision-makers fast enough to change outcomes.

By structuring Contextual’s proprietary AI Orchestration platform around effective delivery of those patterns, where configuration and extension are unique to a client’s business need, we are able to deliver the power of AI transformation to any number of lower mid market companies with speed, scale, and high ROI.

The successful completion of our partnership with Southfield Capital marks just the beginning of this journey. We're very grateful to have found partners who share our vision for AI-driven transformation, and we're ready to execute with the team and technology to make it real.