Winstead PC connected four core systems into a Microsoft Fabric data lakehouse with Harbor Connect, reaching value 80% faster than point-to-point integration.
How Winstead unified its law firm data for AI
Winstead PC, a Texas-based law firm, worked with Harbor to connect four core systems into a single data lakehouse on Microsoft Fabric using Harbor Connect. The firm now ingests more than five million records per hour and reached value 80% faster than a legacy point-to-point integration approach. That foundation supports the firm's business development, matter pricing, and internal AI assistant, Ask Pete.
Snapshot
Why most law firm data architecture goes unquestioned
Christopher Di Masi, Chief Information Officer at Winstead PC, doesn’t mince words about the way most law firms handle data:
“It is plumbing. It moves the water. But it works because we’ve all decided, as a legal industry, that that’s just the way it must be. And there are a lot of reasons that plumbing exists, and nobody tries to change it. I don’t think they’re good reasons.”
There is a version of technology leadership that keeps the lights on, manages the stack, and delivers what has always been delivered. Di Masi has spent nearly fifteen years making sure that version never fails. He is also the person who decided it was no longer enough.
Winstead is a Texas-based law firm that competes at a level its headcount alone does not explain. The firm has built a reputation for punching above its weight, and Di Masi attributes a significant part of that to a technology culture that takes disruption seriously, and a leadership team willing to absorb short-term friction for long-term advantage. When the opportunity came to rebuild the firm’s data foundation from the ground up, the question was never whether. It was how, and with whom.
How the financial system limits law firm reporting
For most law firms, the financial system sits at the center of everything. Every other technology platform is built around it, reporting flows through it, and data that lives inside it is difficult to relate to data that lives anywhere else. The result is a reporting infrastructure that reflects decisions made decades ago, optimized for stability rather than intelligence.
“So much data sits in the financial system,” Di Masi explains. “And there are so many opportunities to relate that data to data from other systems. It’s really difficult to do that with the traditional plumbing we have today.”
When a practice leader or a member of firm leadership needed an answer, producing it meant working through reporting mechanisms that had not fundamentally changed in a generation. Those mechanisms were slow, rigid, often manual, and disconnected from the data sitting in adjacent systems.
At the same time, the firm had reached a natural inflection point. A major financial system migration had been completed, bringing Winstead onto a modern platform and creating, for the first time, a real opportunity to rethink how data moved through the firm. Di Masi saw the migration as the moment the real work could begin.
Why Winstead treated integration and its data foundation as one project
Di Masi designed the project as a single move, treating integration and data foundation as inseparable from the start.
“It’s all one thing,” he says. “I don’t need to just fix the problem. I need to fix why the problem is happening, all the way down to the root. If you just fix things on the surface, it doesn’t help. And it makes it worse when you have to do it down the line, because you’re going to have to redo it.”
The project Harbor and Winstead designed together reflects that philosophy. Rather than connecting systems to serve existing reporting needs, the goal was to rebuild the data foundation itself: a lakehouse architecture that ingests data from across the firm’s core platforms, normalizes it, and makes it available for reporting, business intelligence, and, eventually, AI, without any single system acting as gatekeeper.
Today, data from four of Winstead’s core platforms flows into that lakehouse at a rate of more than five million records per hour, the starting point for a foundation the firm plans to expand rapidly. Winstead had been evaluating a more conventional route, building the lakehouse using legacy point-to-point integration tools. Harbor Connect got there 80% faster. What was once siloed, slow to access, and difficult to relate across systems is becoming a foundation for firm intelligence and optimized client service.
For Di Masi, the bigger payoff is a different way of working with data.
We are only limited by our creativity now. We get to sit down with stakeholders and build exactly what they need, instead of handing them the same siloed, disparate data we always have. Christopher Di Masi, Chief Information Officer at Winstead PC
Why Winstead chose expertise over an off-the-shelf integration tool
Winstead had options. The market for data integration is crowded with tools that promise to solve exactly this problem. Di Masi chose differently, and the distinction matters to him.
“I’ll always take expertise over the tool, every time,” he says. “You can buy a tool. They have legal-specific options, something that’s designed to accommodate all law firms, not a specific law firm. And yes, we do a lot of the same stuff that other law firms do. But the way we do it is so specific to Winstead.”
What Harbor brought was a team with deep, operational knowledge of the specific systems Winstead runs, systems Harbor has lived in, built on, and optimized for firms like Winstead for years. That legal-specific knowledge shaped how the project was designed before a single line of code was written.
“What Harbor came to me with were ideas about our own systems that I’d already been thinking about for a long time,” Di Masi explains. “To hear someone else say it back to me instantly creates confidence. They didn’t just say, yeah, we can do it. They talked through exactly how they’d get there.”
Di Masi committed to the project early, before the full solution was built. That decision, he says, was the result of a long relationship, across multiple engagements and across the firms that eventually became Harbor, combined with the direct experience of sitting across the table from people who understood his firm’s problems as well as he did.
“Harbor listens,” he says. “But more than that, Harbor is grounded in what can actually be delivered. A lot of providers will say yes and move forward without understanding where the real obstacles are, and then the project stalls. My experience is that Harbor knows exactly where those obstacles sit and gets specific about how to clear them.”
That expertise showed up in the specifics. When the project reached the point of configuring Winstead’s environment in Microsoft Fabric, Harbor brought in dedicated security specialists to advise on the setup, giving the firm full, direct control from within its own Azure environment rather than depending on a vendor’s black box.
Absorbing scope changes without losing pace
Like any technology project, this one had its share of external challenges. Infrastructure provisioning in the cloud environment created delays that were outside anyone’s control. More significantly, the scope of the project expanded mid-course when the firm identified an additional reporting workstream it wanted to bring into the lakehouse.
“That was a late add,” Di Masi notes. “And it’s a testament to the team, it was almost a blip in terms of realigning resources and addressing it. It was a non-factor. It didn’t impact the pace of the project at all. And I think that’s incredible.”
That adaptability reflects something Di Masi considers fundamental to how Harbor works. Unlike engagements that end at go-live, Harbor’s involvement in Winstead’s data foundation continues well past go-live. The team advises, implements, and continues to manage, so the knowledge behind the foundation stays in place long after the project closes.
“Oh, absolutely,” Di Masi says, when asked whether that continuity matters. “Harbor has always been grounded in what can be delivered and managed beyond go-live. We understand the obstacles together. And that’s what I like about Harbor.”
How a unified data foundation supports business development, pricing, and AI
The immediate outputs of the project, a unified data lakehouse, normalized records across core systems, faster access to firm-wide data, are significant on their own. For Di Masi, connecting the firm’s systems was never the finish line. It was the foundation for the bigger ambitions he’d held for the firm long before this project began.
“I’ve always known Winstead could operate at a higher level,” he says. “That’s what’s exciting about working with Harbor on this. Every day I talk to someone on the team and realize we’ll get there faster, or get there at all, because of what we’re building.”
Business development is where he expects the impact to show up first.
“The impact on business development is going to be dramatic,” he says. “It will enable us to deliver business development data to attorneys at the point of business development, exactly the kind of information they need. Experience data. Relationship data. Client and company snapshots on their phone, through a natural language query. Managing pipelines. That’s a big deal.”
Todd Arritola, Winstead’s Chief Business Development and Marketing Officer, sees the same opportunity through the lens of client service. “The real opportunity created by this data foundation is to improve how we serve our clients. By putting relevant experience, relationship history, and client context in front of our attorneys at the right moment, we can better understand each client’s business, anticipate their needs, and bring the right people and insights to the table. This is not simply a better way to develop business. It is a more informed and connected way to help our clients achieve better business outcomes.” he says.
Beyond business development, Di Masi sees the data foundation as the prerequisite for something larger: a form of AI that is Winstead’s own, built on Winstead’s own intellectual property, producing insights that no other firm can replicate because no other firm has the same underlying data.
That future is already taking shape. Winstead has built its own internal AI assistant, Ask Pete, and the unified foundation Harbor Connect created is what lets Ask Pete draw securely on the firm’s real, current data rather than a fragmented or outdated slice of it.
“The hope is that we’re doing it with AI that is not this homogenized version, but AI that is Winstead proprietary,” he says. “Something that other law firms aren’t offering because it’s Winstead’s intellectual property that is exposed to our AI.”
Pricing and matter intelligence are also in view. The firm’s current approach to pricing a new matter depends heavily on finding a comparable matter in the financial system and working from there. What Di Masi is building toward is something richer: a model that draws on what was actually done in a matter, documents drafted, time dedicated, the nature of the work itself, matched against a natural language description of the incoming matter, to produce pricing that reflects reality rather than precedent.
“I think that’s one of the most exciting components of standing up all of this,” he says, “the ability to not only pull the data easily but to map to other firm data sources to provide optimal client service.”
Old systems get solidified in concrete. You have to go through the pain right away. You have to. Everything changes too quickly. To wait is insane. Christopher Di Masi, Chief Information Officer at Winstead PC
Advice for law firm CIOs preparing their data for AI
Di Masi is clear about the risk of inaction. Firms that defer this work, he argues, only make the eventual reckoning harder.
His advice to peers is equally direct, and it starts with relationships.
“You have to be embedded with the other leaders in your firm and understand the problems they’re facing,” he says. “That’s the only place to start. You can’t just sit back and be reactive. You have to be proactive. You have to dig into other departments and understand what’s going on there, what data they collect and what they need to retrieve to make work better, beyond the high level, at a granular level.”
The parallel to how Harbor approaches an engagement is deliberate. When Harbor sits down with a firm, it brings the domain experts the conversation requires, whether that is someone who understands the financial systems, the business development platforms, or the operational workflows that connect them. The goal is the same as Di Masi’s: understand the problem all the way down to the root before proposing a solution.
“When something comes up that needs Harbor’s input,” he says, “they bring the right resources into the room. If it’s a finance question, they’re talking to finance, and they have people who can actually answer what finance is asking.”
For Winstead, the result is a firm that will be measurably different from its peers, because it built the foundation that makes AI, business intelligence, and operational clarity possible in the first place.
“I believe this will differentiate Winstead significantly from other law firms,” Di Masi says. “We will stand out because of our application of technology and this reorganization of how law firms deploy systems. And this allows us to deliver what clients are looking for today.”
About Harbor Connect
Harbor Connect is Harbor’s integration and data management service, connecting the systems and data that run a legal business, then managing them as one. Built on decades of legal-native expertise across the platforms law firms and law departments depend on, Harbor Connect combines advisory, implementation, and ongoing management so the technology a firm invests in works as one and keeps working.
About Winstead PC
Winstead is a leading Texas-based law firm serving clients across the country. We work with public and private companies, governments, individuals, universities, and public institutions.
Winstead’s business transactions and litigation attorneys serve key industries, including real estate, financial services, investment management and private funds, higher education, public-private partnerships, airlines, healthcare and life sciences, sports business, tax, and wealth management.
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