Chief Technology Officer

Chief Technology Officer - Philadelphia

THE OPPORTUNITY

Pond Lehocky Giordano LLP (PLG) is one of the largest plaintiff workers' compensation law firms in the United States and the dominant firm in Pennsylvania across workers' compensation, Social Security disability, and personal injury. We are also the founding firm behind Case Xchange, an award-winning law firm-to-law firm referral marketplace that integrates with Litify, Clio, and CASEpeer.

We are hiring our first Chief Technology Officer to lead PLG's technology function into its next chapter. This is a build-and-operate role: you will own a mature, well-run IT and platform operation while simultaneously architecting the AI-driven future of how a high-volume plaintiff law firm acquires, evaluates, and resolves cases. The right candidate will see this as one of the more interesting CTO seats in legal services today.

THE MANDATE

1\. Own PLG's technology strategy end-to-end.

You will set and execute the multi-year technology roadmap for the firm. This includes our case management platform (Litify on Salesforce), telephony, marketing technology, business intelligence, and the cross-functional data infrastructure that powers everything from intake to settlement.

2\. Lead PLG's AI transformation.

AI is the center of gravity for this role. You will personally lead vendor selection, build-vs-buy decisions, and production deployment of AI capabilities across intake qualification, document review, medical record summarization, settlement modeling, and attorney productivity. You will be expected to evaluate platforms like EvenUp, Eve, Harvey, Paxton, and emerging WC-specific tools, and to know when to build proprietary capability instead.

3\. Manage and elevate a strong existing technology operation.

You will inherit and lead a Director of IT (already in seat), a Salesforce / Litify administration team, and a telephony team. Your job is not to run the help desk; it is to be a great executive sponsor for the leaders who do, give them air cover, set higher ambitions, and ensure the operation scales as the firm grows.

4\. Build the data and analytics backbone.

PLG is investing in an enterprise performance dashboard (the "Jumbotron") covering KPIs across intake, marketing, pipeline, and operations. You will own the data architecture that makes this and future analytics initiatives possible — clean data flowing from Litify, telephony, marketing platforms, and finance into a single, trusted source of truth.

5\. Serve as technical advisor to Case Xchange.

Case Xchange is a related but separately led entity. As CTO of PLG, you will provide a defined advisory contribution to Case Xchange's product and engineering team — perspective on architecture, AI, and platform decisions — without product or delivery accountability there. Time allocation is capped at approximately 10 percent. Case Xchange's technical leadership does not report to you.

WHAT SUCCESS LOOKS LIKE IN YEAR ONE:

• Strategy. A published, board-endorsed three-year technology and AI roadmap with clear capital and operating budget asks.
• AI. At least two production AI deployments with measurable impact on intake conversion, attorney productivity, or case cycle time.
• Data. The Jumbotron dashboard is live, trusted by the executive team, and used in weekly operating cadence.
• Operations. A stable, well-led IT and platform organization with documented service levels, a refreshed vendor portfolio, and improving employee satisfaction with internal technology.
• Case Xchange. A clear, scoped advisory rhythm with Case Xchange's engineering leadership that adds value without creating role confusion or time leakage.

THE PERSON WE'RE LOOKING FOR:

Required experience

• 10–15 years of progressive technology leadership experience, including at least 5 years in a senior technology executive role (CTO, VP Engineering, VP Product Engineering, or equivalent).
• Has personally led the deployment of AI or machine learning systems into production with documented business impact. Can speak fluently about LLMs, retrieval-augmented generation, fine-tuning, evals, and the build-vs-buy economics of AI.
• Operating experience at a mid-market services or platform business in the $50M–$500M revenue range. Strong preference for legal technology, insurance claims, healthcare revenue cycle management, financial services, or another document-heavy, workflow-intensive industry.
• Has owned a technology operations function (IT, infrastructure, end-user computing, or platform administration) — even if it was not the part of the job they loved. We are not hiring a researcher.
• Salesforce ecosystem fluency. You do not need to be a developer, but you need to understand the platform's architecture, economics, governance model, and limits. Prior exposure to Litify, Clio, CASEpeer, or comparable case management platforms is a strong plus.
• Demonstrated success leading and developing senior technology managers. You will manage managers.

COMPENSATION AND LOCATION

This is a Philadelphia-based, in-office role. Compensation is competitive with mid-market technology executive packages in the Philadelphia and Northeast corridor and includes base salary, performance bonus, and long-term incentive components calibrated to the candidate's experience. Specifics will be discussed with finalists.