Introduction
Bill Price is a 3x tech general counsel (“GC”) with over 20 years of experience leading disruptive start-ups, private equity-backed turnarounds, and public companies. Bill recently helped lead the sale of Sungard, and is now exploring new GC opportunities. He also leverages his extensive experience and the power of legal AI to provide fractional general counsel services at flat, monthly recurring fees to companies of all sizes. Bill also provides mentoring, coaching, legal AI ops consulting, and other career advice to General Counsel (and those aspiring to be).
Most recently, Bill was Chief Administrative Officer, General Counsel, and Corporate Secretary at Sungard Availability Services. Bill led Sungard’s Legal, HR, Corporate Development, Contracts, and Compliance functions through major business transformations and two changes of control. His career spans the evolution of disruptive technology from the early days of the internet, e-commerce, SaaS, and cloud computing, up through today’s AI revolution. Bill has built and scaled global, cross-functional departments numbering from one to hundreds of employees. Bill’s successfully closed more than $25 billion in corporate commercial, capital markets, and M&A transactions.
Bill is also a Wharton-certified leader in AI and Analytics, a member of The L Suite (TechGC) community, and on the Advisory Board of Emma Legal [Website: Emma Legal], a legal AI company whose platform automates and augments legal due diligence in M&A transactions.
Given his decades of global in-house experience and extensive use and knowledge of AI, Bill brings a unique perspective on how cross-functional legal leaders can drive growth while effectively managing enterprise risk.
From Law Firm Litigator to Corporate Leader: A Career Journey
Zac: Bill, to kick things off, can you introduce yourself and share a bit about your background, how you started out in law, and ultimately became a GC?
Bill: Sure. When I graduated from college, I was originally interested in medical school but opted for law school because it was faster to get a degree, three years instead of seven, and I needed to start working. During law school, my first legal job was clerking for a small litigation boutique in NY where I was trained and mentored by some great trial lawyers. They taught me how to try a case before a jury, and I loved it. Thus, after graduation, I joined the firm, and early on, I was in court almost every day.
Over time, however, courts became clogged, and trial lawyers spent less time in court and more time in discovery, chasing paper. I didn’t enjoy that change, so I began exploring other career opportunities.
I was eventually introduced to an entrepreneur, Chris McCleary, who had the disruptive idea of selling software as a service. He needed a General Counsel for his new company, USi. I had never been a GC before, but to paraphrase Brad Smith, former GC and current President of Microsoft, I leapt before I learned. At the time, my wife and I just had our first child, so it was a risk to join a start-up, but one we were willing to take. That risky decision really set me on the successful career path to where I am today.
We successfully grew and took USi public, but when the internet bubble burst in 2000, so did most of our early adopters’ revenue. Thus, we had to restructure the balance sheet and were taken private by Bain Capital, which saw that we had the right SaaS and e-commerce strategy, but were slightly ahead of our time. As the brick-and-mortar companies began to adopt e-commerce and sell their wares online, our revenues grew again, and we eventually sold the company to AT&T. I stayed on at AT&T for a couple of years, helping the enterprise sales teams integrate and sell managed application services into their network and mobility bundles. AT&T was a big cultural shift from startup life, but I worked with and learned from a lot of smart people and helped bring a more entrepreneurial and less risk-averse mindset to the corporate team.
I was subsequently solicited by my former CEO at USi, Andy Stern, to join Sungard and assist Bain, Silver Lake, and several other large PE investors in turning around and spinning off the services business from the software division, which was subsequently sold to FIS for $9.1B. After 10 years of operating, we’ve now wrapped up the sale of Sungard’s remaining cloud and recovery services businesses. I am now beginning to explore new full-time GC opportunities, as well as providing fractional GC, consulting, and legal ops services on a subscription fee basis to companies and other GCs.
Lessons Learned as a GC
Zac: Looking back at your time at USi, what lessons did you take from building a legal function there?
Bill:I was employee number five at USi. At our peak, we grew to about 1,200 global employees. As mentioned above, this was my first GC role, and it was initiation by fire. My charter was to “get things done while keeping us out of jail”. In other words, to be a businessperson first, with legal acumen. The early training and instruction I received, especially from our founder Chris McCleary, shaped how I still approach the GC role today. Specifically, to get things done, work smarter, not necessarily harder, and if asked, accept the job, even if you don’t “have the time” or “know what you are doing”-you will figure it out. This last lesson about taking on new roles is one I often teach to lesser experienced GCs today who want to grow and become cross-functional. It’s how I define “experience”-being comfortable, initially, not knowing what you are doing-you will figure it out, by doing and getting help from others.
At the time, software usage was changing rapidly, moving from licensed, on-prem solutions to a managed subscription service, hosted in 3rd party data centers, now known as the “cloud”. It was the early days of the internet, and the rules and regulations around IP, data privacy, and security were unclear, just like in AI today. Those early days of SaaS and cloud taught me, forced me really to be creative, less risk-averse, and work more collaboratively, especially with product, security, and finance SME’s.
As USi and the industry grew, I wanted to scale the legal team, but there were always budgetary constraints. I had to constantly reprioritize and accept the ever-increasing risk profile the business was willing or needing to take. That is the reality of being a GC – your job is to focus on and mitigate real risks, not imaginary ones, and make clear, concise recommendations to the business on how to achieve its growth objectives in light of those risks.
You won’t have perfect facts nor enough time, but you will still be asked for a definitive answer. Sometimes, the most important answer is “I don’t know, but will quickly get back to you”. In other words, don’t fudge it. Your credibility depends on you being able to back up your answer with reason and judgment – something AI can’t do yet. If you don’t know, say so, but follow up asap and within the time frame you set. Being responsive is one of the key tenets of being a successful GC.
Even if your recommendation is not accepted, and provided the ultimate decision made is not illegal, you must fully support it and persuade others to do the same, notwithstanding any increased legal risk. It’s your job as an in-house legal leader to accept the decision (and convince others to do the same), mitigate the risk and help achieve the objective. Successfully balancing risk with accomplishing the business objective is what makes an effective in-house lawyer and GC.
The key is to become the trusted legal and strategic business advisor to the C-suite and the board. Trust is earned over time and will get you into the room where strategic decisions are made. To earn this trust, you need to develop relationships with your fellow C-Suite leaders and understand what problems they are trying to solve from a customer perspective. Learn the business inside and out-from a product, operations, financial, and cultural (especially with respect to risk profile) perspective.
Zac: What ultimately drew you to Sungard? And tell us a bit about the company and your role there.
Bill: My past relationship with the CEO, Andy Stern, and Bain Capital (both of whom I worked with at USi). But for them, I most likely would not have joined Sungard. Like most job opportunities, it came through the relationships I had and the people I knew.
Sungard had a strong brand, a great customer base, and very service-oriented, loyal employees. The Legal Dept was extremely talented, yet the Company was outsourcing much of the legal work, which I believed the in-house team could do better, faster, and cheaper. To free up the in-house lawyers’ time to do more legal work, we shifted much of the sales and procurement contract negotiation work the lawyers had been doing to lower-cost contract specialists. This freed up the in-house lawyers to do more of the specialized legal work, such as compliance, board and entity governance, immigration, employment, and environmental law. This insourcing saved millions of dollars of external counsel fees, turned the Legal Dept. into a strategic profit center and helped retain and grow the careers of our in-house counsel and contract specialists.
The Fundamentals of Effective In-House Leadership
Zac: From your perspective, what are the most critical traits of an effective in-house legal leader today?
Bill:Foremost is to develop a high level of trust with the board and the other C-level executives. They need to trust that they can rely on you and your team to help them achieve their strategic objectives while minimizing material risks.
To build that trust, you need to take the time to develop relationships with key cross-functional leaders to understand their challenges and risks. Pre-COVID, such relationship building would happen mostly in person, but today, with much of the workforce still virtual, video meetings must be utilized. Frequent communication and collaboration, even if virtual, are essential. If you do not get to know the intricacies of the business and the people running it, you simply will not be effective as an in-house leader. You need to build relationships and trust so that your colleagues are comfortable sharing what keeps them up at night, even when those issues are not strictly legal.
Zac: What are some practical ways a new GC can start building that kind of trust, especially when stepping into a situation where the business may not have had positive experiences with lawyers in the past?
Bill:First, recognize that stereotypes exist, and if you had a predecessor, their reputation may influence how people initially view you. You cannot build trust in a day, and it is difficult to do so in the middle of a crisis. Ideally, you schedule in-person or virtual meetings with the key people early on, before the inevitable first fire drill. That way, when an urgent issue arises, you are not starting from scratch, spending precious time learning who the stakeholders are, what they do, and what their challenges and risks are.
One of the most important relationships a GC has is with the CEO. The values, culture, and objectives of the organization start with the CEO, so it’s important that you two are aligned and have regular one-on-one meetings to maintain that alignment. The other relationship a GC must cultivate (especially if the GC is also Corporate Secretary) is with the board chairperson. The GC should either report directly to the CEO or to the board chair. If to the CEO, it’s important that the GC have a dotted line to the chair and meet regularly in between board meetings to discuss required and recommended board agenda and action items to avoid surprises and run more effective board meetings. If the GC and CEO have a trusted relationship, the CEO should encourage and want the GC to meet separately with the chair-it’s just good governance.
These early conversations are not about solving legal problems. They are about building relationships and trust, so that when the real challenges come, you already have the foundation to effectively work together.
Managing Global Teams and Cultural Dynamics
Zac: You have managed legal and other cross-functional teams across many different regions of the world. What leadership lessons have you learned from working across cultures and geographies?
Bill:Ideally, when you first join an organization or get promoted as a manager, you meet with your teams in person. However, when that is not possible because of virtual workforces, budget, and/or time, you can leverage the great video tech available to get regular “face time” with your staff. Regular video calls make a difference because you see each other, not just hear each other. And yes, we urge employees to be on camera unless personal circumstances dictate otherwise.
Management is a learned skill, not an inherent trait. Having worked in tech most of my professional life, I have seen countless times when a great engineer, data center operator, or lawyer is promoted into a management role with no prior management training! This often sets up a very valuable employee for failure, resulting in attrition, cultural indifference, and poor performance. There are 3 main management skills I have learned through the years, and which I now coach others on:
- Before the work begins, define what success is. With input from your team, create clear, unambiguous department objectives and tie them back to the corporate objectives that the company performance (and usually the employee bonus plan) will be measured by. These objectives should be regularly checked and updated, as need be, during periodic performance reviews.
- Delegate. Whenever I am hiring or promoting from within, my goal is to always select people smarter than me. If I’m successful in that regard, delegation becomes even easier, and performance improves. Employees learn by doing and by giving them the opportunity to make and learn from their own mistakes. It’s a bit ironic but true in my experience-the more skills and opportunities you give an employee to enhance their resume, the longer they will stay. Micro-management has the opposite effect.
- Scheduled and ad-hoc check-ins. Regular catch-ups with reports are critical to build rapport and trust. Delegate but have their back and support to pitch in as requested. Resist the urge to take over. Equally important are skip-level one-to-one meetings. It’s critical for leaders to hear directly from front-line employees. Inevitably, you will learn things about improving the business, your team, management style, and overall leadership effectiveness you would not otherwise hear from your direct reports. It’s a great 360 exercise. The level of comfort your direct line managers have with you speaking with their reports, and their candidness in those meetings, are good cultural barometers of the level of trust in your organization and your effectiveness leading it.
One other simple but meaningful hack for global managers is to be mindful of time zones when scheduling meetings. It might be convenient for me to schedule recurring team meetings at 9:00 AM ET every Tuesday, but that is 7:30 PM in India. Thus, I try to rotate the timing of meetings so that each team, irrespective of size, is on occasion equally inconvenienced according to their time zones. This simple scheduling awareness has a meaningful, positive impact on global culture and team bonding.
AI and the In-House Legal Function
Zac: Let’s shift into AI. It feels like things are changing by the minute. How do you see AI impacting in-house legal?
Bill: Things are certainly moving at warp speed! I view AI as a critical tool for in-house lawyers. In my opinion, AI won’t replace lawyers, except perhaps those who refuse to use it. Rather, legal AI will augment and enable in-house counsel to be less administrative and more strategic, including freeing up time to lead other functions and hopefully improve work-life balance. Many of the repetitive tasks that don’t require much, if any judgment, such as NDA’s can be automated, enabling self-service by sales and procurement teams, which in turn will increase deal velocity. Perhaps the biggest current concern isn’t being replaced by AI as much as FOMO-falling behind. It’s helpful to remember we are still in the very early stages of AI. Thus, resist the urge to splurge on a tool prior to first figuring out the problem you are trying to solve with AI. These steps are helpful as you start your journey:
- Decide, ideally with a team of cross-functional experts, whether you want to start with low-hanging fruit or tackle more complex, high-value problem areas. Either way, the goals should be the same-greater efficiencies leading to better performance and revenue growth. After you have decided which pain point to attack, the following steps can be very helpful in choosing the right AI tool:
- Gap assessment, including interviews, process mapping, and review of existing tools, may reveal quick wins using platforms already in place, such as CMS or CRM
- Pick 2-3 vendors under NDA and give them your business case, not theirs, to solve
- Crowdsource intel (in-house SME’s, Industry & AI conferences, Substack, Reddit, professional communities such as the L Suite, etc.) to survey users and reviews
Adoption is critical. You can build the best AI tool, but if nobody uses it, it fails. You also need to be thoughtful in evaluating vendors and getting the right (i.e. shorter, no training on data) contract terms in place, as AI changes constantly and there will be vendor consolidation, commoditization, winners and losers as the nascent legal AI industry begins to mature. The key is to just start, but start smart.
Zac: Can you give an example of what you mean by low-hanging fruit versus more material applications?
Bill: As mentioned before, a common example is NDA’s. They are usually the first step in every sales or procurement cycle and are typically pretty standard. Thus, you can create a simple playbook, post the NDA form, and fall-back parameters leveraging your legal AI tool of choice (including turnkey or custom). Ideally, a tool that connects securely to other internal API’s, such as Slack, for self-service by Sales. This AI-enabled process lets the business execute NDAs without much, if any, legal involvement. Another “low-hanging fruit” could be marketing or PR reviews. These examples free up the legal team from the more mundane, administrative tasks and lets them focus on legal and strategic work that requires judgment, context, collaboration, and material risk assessment.
Higher up the strategic stack are commercial sales agreements. Different customers will often redline the same contract provisions. AI can analyze those redline patterns and automatically update the template so it reflects what the market consistently demands. This results in reduced sales cycles and a contract that is a negotiated template and market differentiator.
Zac: You have also advised legal AI start-ups and Legal Ops executives on how GCs do their jobs and what they need from AI to scale their departments and become more strategic. What are you seeing from the vendor side that excites you?
Bill: As a broad legal research and redlining tool, I use GC AI [Website: GC.ai], whose founder is a 3x tech GC, and therefore well understands what in-house teams need in terms of functionality, confidentiality, and data privacy. For example, GC AI does not train on your data, which is encrypted at rest and in transit, as well as segregated from other customers’ data. These protections are table-stakes for legal AI to be used by in-house counsel.
Other legal AI tools are more vertically integrated, such as Emma [Website: Emma Legal], which automates legal due diligence in M&A transactions, and Decover AI which provides a platform to streamline legal workflows, particularly in litigation and eDiscovery.
Another development is that legal AI companies are partnering with Big 4 accounting firms or BigLaw, such as Harvey, or, in the case of Eudia,acquiring an AI-enabled law firm to provide “augmented” legal services at much lower rates than BigLaw, leveraging the efficiencies of AI to provide a legal “brain” tailored for each client.
Lastly, agentic legal AI, such as whatFlankis offering, is expected to grow and become more common in the near future. Specifically, AI agents embedded in legal workflows that can autonomously do certain tasks. Still very early days, and ethical challenges remain, including obligatory “human lawyer in the loop” requirements. However, I do believe agentic legal AI will play a larger role in the near future. Similar to Arizona and certain foreign jurisdictions now allowing law firms to be owned by non-lawyers, I believe we will see ethics rules recognize and allow the use of fully agentic legal AI, and perhaps even synthetic personas, provided a human lawyer remains ultimately responsible.
All of these legal AI tools have the ability to save in-house teams valuable time and money, which can now be better spent on more strategic tasks and career development.
Zac: Looking ahead, what do you think the in-house legal department will look like in the next five to ten years?
Bill:The core challenge has always been to do more with less, cheaper and faster. I do not see that changing. I also don’t see the critical need for a lawyer’s insight, judgment, and trusted advice going away. What I do see is a shift in how and what in-house work is being done. AI will allow lawyers to insource more work from law firms and become more strategic in the enterprise. Much of the lower-level administrative, research, due diligence, and transactional work will be augmented and, in many instances, replaced by AI.
Greater adoption of legal AI will increase the leverage in-house counsel have with law firms to dictate lower rates for certain matters and obtain alternative fee arrangements. That said, I do not believe the law firm billable hour is going away, and hourly rates in certain specialties and under exigent circumstances will continue to rise as firms seek to mitigate the margin erosion caused by legal AI.
In summary, I believe these legal AI developments are, on balance, very positive for in-house counsel-making them more valuable in their roles and giving them greater career growth opportunities because they have more time and are better equipped to tackle increasingly complex, strategic matters themselves.
Zac:Any final advice for GCs who may be hesitant about AI?
Bill: My advice is simple: just start. If your company is not yet ready for a full-blown AI implementation, use it personally to learn its capabilities so that you are more knowledgeable to advocate where and when your company should leverage it. Pick one tool and one objective. Aim for early wins, learn from setbacks, and build from there. This is a once-in-a-generation career development tool. Lawyers who embrace it will thrive.
AI Bubbles, Career Growth, and Leadership Beyond Legal
Zac: You lived through the dot-com boom and bust. There is a lot of chatter now about whether AI is just another bubble. What is your perspective?
Bill: I think the current market environment for AI, and legal AI in particular, is distinct from the dot-com days of the early internet. Yes, both involve transformative technologies. But the underlying economics, maturity of infrastructure, and valuation metrics are completely different. Many dot-com companies were not profitable, and valuations were based on “page views” or miles of cable laid in the ground in anticipation of future demand, not actual revenue. They were early adopters of e-commerce platforms because many could not afford to lease physical storefronts, like the well-established, profitable brick-and-mortar companies.
Today, demand for AI is both real and growing, and coming from profitable companies with real balance sheets and millions, if not billions, of capital to spend. These companies are not Pets.com nor Webvan. AI models are functional, with real-world use cases, and their adoption is growing exponentially every month. Cloud infrastructure makes AI deployment instantly scalable, with the only limitations being sufficient power and real estate to keep up with the demand. Lastly, ROI is beginning to emerge with one early adopter, JP Morgan, just announcing that their $2B in AI investment is now break-even and will soon be accretive to their bottom line. As Jamie Dimon said, this is just “the tip of the iceberg”
Zac: Beyond technology, what advice would you give GCs about expanding their leadership impact?
Bill: I would encourage GCs to take on additional responsibilities outside of legal when the chance arises. Especially now with the efficiencies and time savings brought by AI, it is a golden opportunity to broaden your scope, increase your value, prove your business skills and grow your career.
Mentoring and Coaching: Giving Back to the Profession
Zac: If someone wanted to work with you as their coach or mentor, are you open to that?
Bill:Absolutely. In addition to being a GC and running my subscription-based, AI-powered law firm, Subscription GC, I also operate a consulting practice, Teach GC, where I mentor and coach GCs as well as in-house counsel on how to become a GC and prosper once in the chair. I enjoy teaching others the many lessons and practical hacks I have learned doing what I consider to be the best role in the C-Suite, the General Counsel.
I was fortunate to have had a few mentors along the way, and I believe it is important to give forward. As they say, “the wheel turns”. Helping other in-house counsel and GCs in their professional development is a privilege and very rewarding, hopefully as much for them as it is for me. For anyone interested in learning more about my services, just DM me on LinkedIn.
Thanks, Zac-I enjoyed the discussion.
Organizations Mentioned Above
Flank Flank (formerly Legal OS) builds autonomous AI agents for enterprise legal teams, enabling them to automate contract drafting, review, and negotiation while staying within policy.
GC AI GC AI is an AI copilot purpose-built for in-house counsel, generating high-quality drafts, legal research, and advice tailored to team style and context.
Emma Legal Emma Legal is an AI platform designed to automate legal due diligence for M&A, scanning data room contracts, flagging risks, and producing structured reports in half the time.
The L Suite (TechGC) The L Suite is an invite-only executive peer community for GCs, CLOs, and in-house legal leaders, providing curated networks, benchmarking, and insights to help them make better, faster decisions.
