$6 - $10/hour – Head of Legal Technology & Legal Operations (Fully Remote – US Law Firm)
$6 - $10/hour – Head of Legal Technology & Legal Operations (Fully Remote – US Law Firm) Reports To: Firm Owner and COO Works Closely With: Practice Group Leaders, Operations, Finance, Marketing, Security Vendors Hours: 40+ hours/week Mandatory Sync Availability:
- At least 25 hours per week between 7:00 AM – 12:00 PM Pacific Time (U.S.)
- Monday–Friday Location: Fully Remote Engagement Type: Independent Contractor (Upwork) Time Tracking: Upwork Automatic Time Tracker – mandatory, no exceptions ________________________________________ IMPORTANT – READ CAREFULLY This is a senior, firm-wide leadership role responsible for how technology actually enables legal work, collaboration, and scale. This is not an IT support role, and it is not compatible with part-time work or side engagements. We are looking for someone who will deeply learn the firm, take ownership of its legal technology stack, and aggressively improve how every tool is used in practice. If you are not excited by complexity, accountability, and continuous optimization, do not apply. ________________________________________ About the Firm Rose Law Firm is a modern, business-oriented U.S. law firm serving middle-market business owners and professional organizations. We handle complex litigation, transactional, and advisory matters and operate deliberately at the intersection of law, business strategy, and technology. The firm is led by attorneys trained at top-tier U.S. law schools and supported by a 50+ person, globally distributed, highly professional team. We are fully remote, systems-driven, and uncompromising about quality. Technology—particularly AI—is a core operational advantage, not an experiment. ________________________________________ Role Overview The Head of Legal Technology & Legal Operations is the firm’s owner and architect of how technology supports legal work. This role does not require a law license, but it does require deep familiarity with legal workflows, how lawyers and paralegals actually work, and how technology either amplifies or undermines quality. You will: •Own the design, configuration, and optimization of the firm’s legal technology ecosystem.
- Aggressively learn how every practice group works.
- Identify friction, redundancy, and underutilized capabilities.
- Turn software into a force multiplier for lawyers, not a burden. This is a hands-on leadership role with real authority and real expectations. ________________________________________ Core Responsibilities Legal Technology Ownership
- Serve as the firm’s internal owner of all core legal and collaboration systems.
- Ensure tools are configured to support real legal workflows, not generic defaults.
- Standardize how technology is used across practice groups while respecting legitimate differences. AI Strategy & Integration
- Lead firm-wide use of AI tools, including: o ChatGPT (individual, business, and enterprise contexts) o Lexis AI o NetDocuments AI Assistant
- Evaluate and advise leadership on overlapping AI offerings and tradeoffs.
- Design AI-enabled workflows for legal, operational, and business use.
- Stay current on AI capabilities and proactively propose high-impact use cases. Platform Optimization
- Own advanced use and optimization of: o NetDocuments (including ND AI Assistant) o Microsoft Office and Microsoft 365 (advanced Word, Excel, Outlook, Teams, SharePoint usage) o Zoom (advanced features, workflows, and integrations)
- Ensure tools are used correctly, securely, and consistently. Continuous Improvement & Legal Ops
- Identify inefficiencies and breakdowns in how technology is used.
- Redesign workflows to improve speed, accuracy, and leverage.
- Create internal standards, playbooks, and best practices.
- Measure adoption and effectiveness, not just availability. Training & Enablement
- Train attorneys, paralegals, and staff on how to actually use tools well.
- Translate technical capability into practical legal workflows.
- Serve as a trusted internal advisor to senior lawyers and leadership. Evaluation & Tool Selection
- Evaluate new tools and vendors as needed.
- Run pilots and proofs of concept.
- Provide clear, experience-based recommendations to leadership. ________________________________________ Required Qualifications
- Significant experience in legal technology, legal operations, or law firm systems.
- Strong understanding of litigation and/or transactional workflows.
- High comfort level with AI tools and enthusiasm for aggressive adoption.
- Systems thinker who can see second- and third-order effects.
- Strong judgment, ownership mindset, and execution discipline.
- Clear, professional written and spoken English.
- Ability to operate independently and drive change without micromanagement. ________________________________________ Preferred Experience
- Prior role as Legal Ops Manager, Legal Technology Manager, or equivalent.
- Experience with NetDocuments and Microsoft 365 in a law firm context.
- Experience supporting distributed or
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