Running a law firm has always required juggling competing demands. But today, the technology layer underneath your practice has grown so complex that it can quietly become its own full-time job. Cybersecurity threats, outdated financial systems, disconnected software, and the constant pressure to adopt AI are pulling attorneys and firm leaders in too many directions.
Sikich recently hosted a webinar to walk through how law firms can get a handle on all of it to become technologically modern. The full recording is available here: Sikich Legal OS Webinar.
If you missed the session, here is what was covered.
Start with the foundation
The webinar opened with a framework that will sound familiar to anyone who has studied organizational behavior: Maslow’s hierarchy of needs, applied to law firms.
The idea is straightforward. Before a firm can benefit from AI or advanced workflow automation, it needs the basics in place. Digital infrastructure, reliable internet, secure servers, and physical office operations form the base of the pyramid. From there, financial operations, document management, and case management build upward. AI sits at the top.
The problem Sikich sees frequently: firms are trying to reach the top of the pyramid without stabilizing the layers beneath it. Sikich’s role is to shore up the foundation so firms can focus on practicing law.
IT and cybersecurity: what a full-service tech department actually looks like
Dustin Miller, principal of Sikich’s Tech360 practice, walked through what managed IT and cybersecurity services look like for law firms of different sizes.
The short version: most firms, regardless of size, have more sophisticated security needs than their current setup can address. Very few have a dedicated Chief Information Security Officer. Even fewer have the monitoring infrastructure to know whether their systems are actually secure.
Tech360 fills that gap by providing:
- A virtual CIO who functions as a true IT executive
- 24/7 security operations center monitoring through Arctic Wolf, one of the largest SOC providers in the world
- Continuous internal and external vulnerability scanning
- Endpoint detection, patch management, and help desk support
Dustin pointed out an important advantage of the outsourced model: modern law firms get the expertise of a team that has seen best practices across dozens of organizations, not just one. And when a firm grows, the team can scale with it rather than requiring a costly leadership replacement.
Tech360 serves firms ranging from $25 million to $500 million in annual revenue, with local presence in Chicago and Northeast Ohio and national capacity for co-managed arrangements.
AI is a platform, not a package
One of the sharper moments in the webinar came from Stan Ong, executive director and AI practice lead at Burwood/Sikich, who joined after a 16-year run as CIO of a global law firm.
His point: too many firms treat AI the way they would treat installing a new case management system. Get the software, configure it, and use it. That approach does not work for AI.
AI requires change management, training and adoption planning, governance frameworks, and guardrails around client data and discoverable information. The technology is the last piece of the puzzle, not the first. Firms that skip the preparation work typically end up with a tool that creates more risk than value.
The webinar poll results reinforced this: document review and drafting came in as the top area where attendees wanted AI applied. That is a legitimate and well-suited use case. But getting there responsibly requires getting the infrastructure right first.
Marketing: your digital front door matters
Kyle Adams, who leads Sikich’s agency practice, walked through the marketing challenges that are specific to law firms. The most common issues he sees are not exotic strategy problems. They are fundamentals that get neglected.
Outdated headshots and bios. Brand materials that are inconsistent or difficult for attorneys to update. Websites written for the firm rather than for the client reading it. A reliance on one or two rainmakers to drive most of the firm’s new business.
The webinar covered how digital search is changing as well. A website optimized for traditional SEO three years ago may not perform the same way in an environment where AI-powered search and large language models are increasingly how people find information. Sikich tracks visibility across AI search platforms and helps firms adjust their content strategy accordingly.
The takeaway: type your firm’s name into an AI assistant and see what comes back. If the answer is thin, that is a signal worth paying attention to.
Financial operations: outsourcing the complexity
Ashley Kegan from Sikich’s client accounting solutions group made the case for fractional accounting services that go beyond basic bookkeeping.
The firms that benefit most from this model are those where the finance function has outgrown the person running it, but hiring a full controller or director of finance feels like too large a commitment. Sikich can step into that role without disrupting the team already in place, handle controller-level work, and help develop internal talent at the same time.
The service scales from firms around $5 million in revenue all the way up, operates primarily remote, and is technology-agnostic. If a firm is already on a specific accounting platform, Sikich will work in it.
Microsoft: more than Word and Outlook
Anthony Senevey, who leads the Dynamics 365 enterprise practice, spent time on a question that comes up often from law firm CIOs: can Microsoft do more for us than it is currently doing?
The answer, increasingly, is yes. The Dynamics 365 platform connects CRM, matter management, accounting through Business Central, Teams, SharePoint, and Power Automate into a unified environment. It is configurable without heavy custom development, which means firms can shape it to how they work rather than adapting to the software.
Copilot is embedded throughout, which means AI-assisted summarization, email drafting, and meeting integration are available within the same platform the firm already uses. For firms that want to reduce the number of vendors they depend on and stay within a familiar ecosystem, this is a meaningful option.
Legal tech: software selection done right
Nick Cirino, Sikich’s industry growth leader for the legal vertical, wrapped the session by walking through what the legal tech team does for firms that are evaluating, implementing, or getting more value out of their existing software.
The work includes case management and document management software selection, implementation support, and process optimization for firms that have already made a purchase but are not getting the return they expected. It also includes AI readiness assessments for firms trying to figure out which tools are worth adopting and how to integrate them responsibly.
One note that stood out: Sikich has migrated firms off 40 to 50 different software platforms and knows the strengths and weaknesses of the vendors in this space, including the stability and financial health of the companies behind the products. That kind of market knowledge is hard to replicate with a vendor demo.
The common thread
Every presenter at this webinar made essentially the same point in their own area: law firms are managing more complexity than they should be carrying internally, and the cost shows up in risk, inefficiency, and leadership bandwidth that could go toward building the practice.
Is your firm carrying more complexity than it should?
The firms that showed up to this webinar were not looking for a quick fix. They were asking real questions about how to build operations that can actually support growth without burning out the people running them.
Sound familiar?
Sikich is glad to have that conversation with you. Schedule a free consultation with the Sikich team to talk through where your firm stands and what a stronger foundation for modern law firms could look like.
Here is a short video clip from our webinar:
The full recording is available here: Sikich Legal OS Webinar.
This publication contains general information only and Sikich is not, by means of this publication, rendering accounting, business, financial, investment, legal, tax, or any other professional advice or services. This publication is not a substitute for such professional advice or services, nor should you use it as a basis for any decision, action or omission that may affect you or your business. Before making any decision, taking any action or omitting an action that may affect you or your business, you should consult a qualified professional advisor. In addition, this publication may contain certain content generated by an artificial intelligence (AI) language model. You acknowledge that Sikich shall not be responsible for any loss sustained by you or any person who relies on this publication.
