Legal Operations Career Development: How to Break Into Leadership Roles and Thrive

Today’s General Counsel Columnist Tommie Tavares-Ferreira will be speaking about legal operations career development and leadership as part of the “The Legal Operative: Think, Act, Lead” panel on May 6, 2025 at the CLOC Global Institute (CGI) in Las Vegas. Fellow panelists include CLOC Board Member Adam Becker and Organon Chief of Staff to the General Counsel Stacy Lettie.

Legal operations has evolved into a critical function within corporate legal teams, enabling professionals to drive efficiency, implement technology, and optimize legal spend. But while the path to a director or vice president role is clear, advancing to the C-suite or beyond legal operations requires leaders to carve their own path. Legal operations career development can be challenging.

Unlike law firm careers, which have a clear progression from associate to partner, legal ops professionals often hit a glass ceiling. Vice president and senior vice president roles are rare, and the concept of a chief legal operations officer (CLOO) remains largely theoretical. Without transitioning to a chief operating officer (COO) role, upward mobility can seem limited.

Let’s explore two fundamental challenges:

1. How to reach a leadership role in legal operations
2. What to do once you’ve hit the “glass ceiling”

Doing the Work and Promoting Yourself to Land a Leadership Role

Unlike other business functions, legal operations lacks a formal educational track—there’s no MBA equivalent, no standardized certification that guarantees a leadership role. That means professionals must be intentional about their growth.

It’s important to do two things: do the work to position yourself as a leader, and promote yourself as a leader. You need to demonstrate leadership-level impact.

On the work front, don’t wait for permission to act. If you see an opportunity for improvement, raise your hand and own it. Leaders don’t just execute—they identify and drive solutions. Then you have to make sure that others know about it. Developing a professional brand demonstrates expertise and opens doors to new opportunities.

Here’s how to do that:

• Identify pain points and solve them: Find inefficiencies in your legal department and proactively work on solutions.  (Example: If contract turnaround times are slow, propose and implement a contract intake system.)
• Take on stretch projects: Volunteer for initiatives that expand your scope beyond your current role. (Example: If legal operations doesn’t own legal budgeting, offer to help finance with legal spend analysis.)
• Work cross-functionally: Leadership requires collaboration—start working with finance, IT, and HR early. (Example: If your legal team is considering AI, spearhead research on available tools and potential implementation.)
• Own a major technology initiative: Technology implementations (CLM, AI, workflow automation) are some of the most visible legal ops projects. Take the lead and showcase the business impact.
• Write and share insights: Publish articles on platforms like Today’s General Counsel, LinkedIn, or your company’s blog. (Pro tip: Share real-world challenges you’ve solved rather than generic “how-tos.”)
• Speak at conferences: CLOC, ACC, LegalOps.com, RLLB, and SOLID are prime venues for legal ops professionals to showcase expertise. (Pro tip: Start by participating in panels or roundtables before pitching a solo session.)
• Engage in webinars and podcasts: Contribute to industry webinars or join legal tech panels. Starting a podcast (like Tom Stephenson and I did with Dear Legal Ops) can also be a powerful way to establish thought leadership.

The Importance of Networking, Mentors and Coaching

Legal operations can be isolating, especially if you’re the only person in your company doing the job. That’s why joining the right communities and seeking out opportunities to work with mentors or career coaches are critical pathways for career growth.

Suggestions:

• Join CLOC, LINK, ACC Legal Ops, LegalOps.com. These organizations provide direct access to professionals who’ve been in your shoes.
• Engage in Slack groups, LinkedIn communities, or legal tech roundtables to keep up with industry trends.
• Connect with GCs, COOs, CFOs, and other business leaders—not just legal ops peers.
• Ask insightful questions, offer help, and actively participate in discussions.
• Build genuine relationships rather than treating networking as a transaction.
• Look beyond legal: Other executives can provide valuable insights into business operations.
• Make it a two-way street: Offer your own perspective on legal technology and process optimization to create a reciprocal relationship.
• Seek coaches with experience in operations, leadership development, and business strategy (not just career coaching).
• Investigate whether your company reimburses coaching expenses through L&D (Learning and Development) budgets or other executive education programs or before you pay out of pocket.

What Comes Next? Breaking Through the Legal Ops Glass Ceiling

Once you’ve reached a VP or head of legal operations role, the traditional corporate ladder starts to feel like a tightrope. You’re highly skilled, deeply experienced, and operating at the top of your pay scale—but there’s no clear next step.

Legal operations professionals are some of the most strategic minds in corporate legal, but the industry still lacks a natural VP-to-C-suite pipeline. That means if you’re ambitious, you have to create your own next step.

Here are four real, actionable paths you can take to break through the legal ops ceiling—and what I’ve learned from those who have done it successfully.

1. Become an AI Ambassador or Agentic AI Lead

Legal ops professionals are already using the technology drivers of their teams—AI is the natural evolution of that role. As agentic AI (AI that acts on behalf of users) becomes more embedded in legal functions, legal ops leaders will be the ones overseeing AI implementation, governance, and scale. This means that AI leadership is a massive opportunity. While legal departments are hesitant about fully autonomous AI, they need someone to lead AI strategy, ensure ethical AI adoption, and scale efficiencies across legal and compliance teams.

How to get there:

• Start using AI today: You don’t need permission to start learning—though you do need permission from your company to use these tools. Ensure any use of AI is vetted and approved by your organization and you follow their rules.
• Experiment with tools like Gemini, ChatGPT, Harvey, CoCounsel, Spellbook, Ruli, GC AI, and others to understand how AI integrates into legal workflows.
• Own an AI initiative in your department: If your team isn’t using AI yet, be the person who brings it in. Offer to test AI for contract review, playbook generation, or workflow automation and present findings.
• Position yourself as the AI expert: Start talking about AI in internal meetings, external panels, and LinkedIn thought leadership posts. The more you share, the more people associate you with AI leadership.
• Be proactive and don’t wait for permission: If you wait until the GC or CLO asks for an AI strategy, you’re already behind.

Real-Life Example:

Gabe Saunders: As Director of Legal Operations at wellness and fitness company Exos, Gabe spearheaded the implementation of AI-driven contract management solutions. By partnering with LegalSifter, he automated contract ticketing and triage processes, reducing the time per request from 20–30 minutes to just 45 seconds. This initiative not only improved operational efficiency but also contributed to his career advancement within the company.

2. Transition to Business or Strategy Operations

If you love solving problems at a company-wide level, a move into business operations, strategy, or finance could be your next step. Legal ops leaders already have strong financial acumen, data analysis skills, and cross-functional experience, which directly translates into broader operational roles.

How to get there:

• Start thinking beyond legal: In your current role, take ownership of projects that impact the whole company (not just legal).
• Learn business metrics—If you don’t already, start tracking and reporting on KPIs that matter to the entire business, such as revenue acceleration, risk mitigation, and operational efficiency.
• Align with the COO or CFO—Build relationships with senior business leaders. Understand their biggest operational challenges and find ways to contribute legal ops expertise to broader company goals.
• Don’t be too legal-centric: If you want to transition out of legal, your conversations need to shift. Frame your contributions in business outcomes, not just legal efficiencies.

Real-Life Example:

Stephanie Corey: Co-founder of the Legal Innovators Network (LINK) and CEO of UpLevel Ops, a consulting firm focused on strategic legal operations, business process improvement, and leadership development. Stephanie transitioned from a traditional legal ops role to focus on legal operations consulting. Her work emphasizes aligning legal functions with overall business strategy, showcasing how legal professionals can pivot to broader executive roles.

3. Go the Chief of Staff Route: A Step Toward Executive Leadership

A Chief of Staff (CoS) role is perfect for legal ops professionals who excel at strategy, influence, and cross-functional leadership. You become the right-hand to an executive (often the GC, COO, or CEO), helping drive strategic initiatives across the company.

How to get there:

• Start acting like a chief of staff now: Offer to lead high-visibility, cross-functional projects that require executive-level communication.
• If your CEO or GC has big operational goals but no time to execute, step in and drive those projects forward.
• Develop your executive presence – Start presenting to senior leadership and refining your ability to distill complex information into concise recommendations.
• Work on strategic initiatives—CoS roles are about long-term business planning. Volunteer for projects that impact company-wide strategy, such as M&A diligence, company reorganizations, or efficiency initiatives.
• Make sure you’re operating at a strategic level and not just executing like a project manager.
• Build relationships with executives – If you don’t have strong relationships with leadership, you won’t get the opportunity.

Real-Life Example:

Stacy Lettie: With over two decades as an in-house attorney, Stacy transitioned into legal operations and now serves as the Chief of Staff to the General Counsel at healthcare company Organon. In this role, she leads strategic planning and legal operations, demonstrating how legal expertise can be leveraged in Chief of Staff roles.

4. Pursue the COO Path: Scaling Operations Company-Wide

For in-house legal operations professionals, running legal like a business is a core part of the job. You optimize resources, manage budgets, implement technology, and drive efficiency—all of which mirror the responsibilities of a COO at the enterprise level.

In many ways, legal ops leaders already think like COOs—they just apply those skills to the legal function. The transition from leading legal operations to leading company-wide operations isn’t as far-fetched as it may seem.

Here’s how the skills legal ops professionals use map directly to COO responsibilities:

How to get there:

• Start raising your hand for enterprise-wide initiatives. Take on projects that span multiple functions—such as procurement optimization, enterprise risk management, or revenue acceleration.
• Look for opportunities to work with the CEO or CFO—legal ops leaders who build strong executive relationships are better positioned for broader roles.
• Show the financial impact of legal ops projects beyond legal—whether through cost savings, revenue acceleration, or risk mitigation.
• Strengthen your financial acumen. If you don’t understand how your company makes and spends money, start learning now.
• Ask to shadow the VP of business strategy or join cross-functional financial planning sub-committees.
• Start thinking like a business strategist and not just like a legal strategist.
• Become data-driven: COOs live and die by metrics, financial performance, and operational key performance indicators (KPIs). If you don’t use data to quantify your impact, you’ll struggle to make the jump.

Real-Life Example:

Mary O’Carroll:  As Director of Legal Operations at Google, Mary built one of the most well-recognized legal ops teams in the industry. She then transitioned into the Chief Community Officer role at Ironclad, where she focused on community engagement, thought leadership, and expanding the influence of legal technology across industries.

Now, Mary is the Chief Operating Officer (COO) at Goodwin, a global law firm. In this role, she applies her legal operations expertise at an enterprise level, overseeing firm-wide operations, business strategy, and technology-driven efficiencies.

Check out my interview with her on this episode of Dear Legal Ops.

Final Thoughts: You Don’t Have to Wait for a Title to Lead

If you want to move into a legal operations leadership role, the key is to start leading now—even if your title hasn’t caught up yet.

Legal operations career development requires you to:

• Take on high-visibility projects.
• Solve complex problems.
• Build relationships across departments.
• Showcase your expertise publicly.

Once you’ve demonstrated leadership in action, the title and promotion will follow.