Remote Director Flight Operations Jobs in Illinois

The Role

We're looking for a seasoned operations professional to take real ownership of how the firm runs. This is fundamentally a business-administration role — you'll work directly with the Managing Partner on financial planning and reporting, HR and benefits administration, vendor and budget management, and the firm's operating systems — with a client-facing component layered on top, since you'll also serve as the primary point of contact for clients throughout the lifecycle of their case.

This is a high-ownership role at a firm that moves quickly and expects the same from its team. You'll have direct, regular access to firm leadership rather than layers of management between you and decisions. Given the scope, we're looking for someone with 10+ years of relevant experience who can walk in and run this function with minimal ramp-up — this is not an entry- or mid-level position.

What You'll Own

Firm Financial Planning & Reporting

• Maintain the firm's matter-forecasting model — expected timing and value of pending settlements by practice group, using data from our case management system (Clio Manage), to support cash flow and revenue planning
• Track budgets, vendor spend, and cost-per-signed-client across marketing/intake channels; flag variances proactively rather than waiting to be asked
• Prepare recurring financial and pipeline reports to firm leadership

HR & Benefits Administration

• Own end-to-end HR administration: payroll processing and coordination with our payroll provider, benefits enrollment and renewals (health, dental, vision, 401(k)), and new-hire onboarding into payroll/benefits systems
• Coordinate with outside employment counsel on multi-state compliance considerations as our remote team grows across multiple states

Office & Systems Administration

• Serve as the firm's operational point of contact for vendor accounts, subscriptions, and software licensing across a fully remote practice
• Administer access across firm systems (Clio Manage/Grow, Microsoft 365, QuickBooks Online) — including onboarding new hires and fully executing offboarding checklists when someone leaves the firm
• Own our shared credential/access management system and related security hygiene practices

Client Communication & Case Support

• Be the single point of contact for clients — proactive, scheduled updates on case status, what's happening, and what's next
• Field client questions directly (status, timeline, documents, process) and route anything requiring legal judgment to the right attorney
• Own settlement-stage communication: explaining terms and timelines, answering payment questions, and collecting required paperwork (signed agreements, W-9s, payment preferences)
• Assist paralegals with document preparation and filing-related tasks as needed

Intake Coordination & Campaigns

• Oversee the intake pipeline from first contact through signed engagement letter, keeping Clio Grow/Clio Manage current
• Coordinate case review with attorneys and manage plaintiff-recruitment campaign performance and cost-per-signed-client across vendors
• Maintain referral-source relationships and manage post-settlement follow-up

What We're Looking For

• 10+ years of experience in law firm operations, legal operations management, business/office administration, or a comparable role combining financial administration, HR/benefits, and client-facing responsibility
• Proficiency in Excel (or Google Sheets) — pivot tables, formula-driven models, and financial/matter forecasting are a required, tested skill, not a "nice to have"
• Experience administering employee benefits, payroll coordination, and HR compliance
• Comfortable owning a budget, vendor contracts, and financial reporting to firm leadership
• Experience with legal case management software (Clio, Filevine, MyCase, or similar) preferred
• Comfortable being a steady, clear point of contact for clients
• Comfortable working independently in a fully remote, multi-state environment
• Bachelor's degree preferred; will weigh equivalent experience heavily given the seniority of this role
• Nice to have: experience in class action or mass tort litigation specifically; experience managing a multi-state remote workforce

Compensation & Logistics

• Base salary: $85,000–$135,000, commensurate with experience
• Bonus tied to individual and firm performance metrics
• Strong benefits package: healthcare, dental, vision, 401(k) match
• Fully remote — work from anywhere in the U.S.
• Reports directly to firm leadership