Rory Cooksey & Josh Konigsberg on IT Strategy for Law Firm Growth

JUPITER, Florida — In Episode 35 of the AGM Attorney Podcast, host Josh Konigsberg welcomes guest Rory Cooksey to explore how law firms can move beyond reactive “break-fix” IT and treat technology as a strategic investment for your firm’s scalability and brand.

Rory Cooksey is Vice President of Brand and Business Development at WheelHouse IT, a managed IT and cybersecurity provider serving law firms and professional services organizations. He partners with firm owners to modernize infrastructure, strengthen cybersecurity, and align technology with long-term growth goals.

In this episode, Cooksey and Konigsberg discuss topics ranging from cybersecurity risks and outdated infrastructure to AI adoption and remote work. The conversation delivers actionable insights for aggressive growth-minded attorneys.

Key topics discussed include:

• How reframing IT as a strategic investment—not an expense—directly supports law firm scalability and profitability.

• Why outdated infrastructure creates security vulnerabilities and unnecessary downtime that impacts billable hours.

• How proactive IT management reduces ransomware risk and protects a firm’s brand reputation.

• Why the “break-fix” mindset hinders growth and increases long-term operational costs.

• How digitization and cloud collaboration can reduce overhead, enable hybrid work, and improve team morale.

• The risks of using AI tools like ChatGPT without proper security protocols and compliance safeguards.

• Why finding a trusted IT partner is critical for roadmap planning in a rapidly evolving technology landscape.

• How internal “technology champions” can drive adoption and improve firm-wide efficiency.

Cooksey emphasized that law firms must evolve their thinking about technology. “You have to decide whether IT is an investment or just a problem you deal with when it breaks,” he explained. “The firms that scale successfully treat technology as part of their growth strategy.”

Drawing from real-world experience, Cooksey shared how one large New York law firm transitioned from paper-based systems to a fully digital environment. “They had an entire hallway of filing cabinets. Five years later, it’s gone. They downsized their office, enabled hybrid work, and now collaborate seamlessly through the Microsoft ecosystem,” Cooksey noted.

Beyond security and infrastructure, Cooksey stressed that IT decisions directly affect morale, retention, and client trust. “If you’re not billing, you’re not making money. If your systems are down or inefficient, it impacts your bottom line immediately. And if client data is compromised, your brand takes the hit,” he said. “Attorneys spend so much building their reputation—protecting that brand has to be a priority.”

Regarding AI adoption, Cooksey cautioned firms against moving too quickly without guardrails. “Don’t dive into the deep end without your floaties. We’re seeing organizations upload sensitive information into AI tools without realizing the compliance risks. You need a trusted partner who helps you adopt these technologies responsibly.”

When advising aggressive growth-minded attorneys, Cooksey offered straightforward guidance: “Find a trusted partner. Technology changes too fast to manage alone. Work with someone who understands your business goals and can help you build a roadmap.”

Regarding appearing on the AGM Attorney Podcast, Cooksey added, “Doing this podcast was super seamless. The information I got ahead of time helped me prepare for success. If anybody’s thinking about doing a podcast with Josh, I would 100 percent jump on it. The value is certainly going to be there for you.”

To hear more insights from Cooksey and Konigsberg, watch or listen to the full episode below.

 

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Law Firm Marketing Pros

250 S. Central Blvd, Suite 100-A

Jupiter, FL 33458

561-948-5001

https://lawfirmmarketingpros.com/

About Rory Cooksey

Rory Cooksey is the Vice President of Brand and Business Development at WheelHouse IT, a managed IT and cybersecurity provider serving law firms and professional services organizations. He works with firm leaders to modernize infrastructure, strengthen cybersecurity posture, and align technology investments with long-term growth strategies.

Cooksey regularly advises attorneys and business leaders on topics including cybersecurity risk management, digital transformation, cloud collaboration, and responsible adoption of emerging technologies such as artificial intelligence. His work focuses on helping firms improve operational efficiency, protect sensitive client data, and build scalable technology environments that support sustainable growth.

Contact Information:

Law Firm Marketing Pros

250 S. Central Blvd Suite 100-A
Jupiter, FL 33458
United States

Josh Konigsberg
(561) 948-5001
https://lawfirmmarketingpros.com/