Remote Chief Operating Officer Insurance Jobs in Florida

Chief Operating Officer (COO) – Fractional Business Scale Architect

Location: Remote (Must reside in: AZ, CO, FL, GA, IL, MD, MI, NC, NJ, NY, PA, TX, VA, or WA)

Department: Executive Leadership / Operations

Compensation: $110,000 Base | $182,000+ OTE (Scales directly with operational impact)

About Us

Most law firm owners are brilliant attorneys but accidental entrepreneurs. They get trapped in an exhausting cycle of 60-hour workweeks, unpredictable cash flow, and zero scalability.

At How to Manage a Small Law Firm (HTM), we don\'t just give them generic business advice. We install a proven business model. We are a multi-time Inc. 5000 fastest-growing private company and recognized as a "Best Place to Work" because we practice exactly what we teach.

The Opportunity

We are not hiring a traditional, corporate COO to simply oversee existing red tape or manage middle management. We are seeking an elite operational architect to build empires.

As a Growth Partner & Fractional COO, you won\'t be siloed inside a single corporate department. You will step into the driver’s seat alongside multiple law firm owners simultaneously. You will serve as their operational backbone, their strategic second-in-command, and the executive leader who holds them ruthlessly accountable to their own massive growth potential.

What You Will Do (Responsibilities)

• System Architecture: Design, build, and deploy scalable operational frameworks that turn chaotic small businesses into highly predictable, 7-figure enterprises.
• Bottleneck Destruction: Conduct deep-dive operational diagnostics to immediately identify where profit is leaking, where workflow is stalling, and why the owner is bottlenecked.
• Ruthless Accountability: Implement clear KPI dashboards. Teach owners and their teams to manage by hard data, not by feelings, excuses, or "intentions."
• Fractional Leadership: Scale businesses ranging from $1M to $35M+ by acting as the execution-first leader who translates high-level vision into daily operational reality.

What You Bring (Requirements)

• Direct Founder/Owner Fluency: You must have extensive, hands-on experience working directly with small-to-mid-sized business owners. You understand the unique psychology, speed, and challenges of an entrepreneurial founder and know how to guide them from vision to execution.
• 12+ years of elite operational leadership experience as a COO, VP of Operations, or Head of Operations.
• Proven success scaling small to mid-sized businesses ($1M–$35M+)—enterprise-only corporate backgrounds will not be a fit here.
• A "Builder" mentality. You get energy from turning chaotic, fast-moving environments into smooth, predictable operations.
• Strong founder psychology. You know how to collaborate with, advise, and firmly push back on passionate visionaries to execute a plan.
• Execution-first approach. You focus heavily on driving measurable, bottom-line financial and operational results, rather than just delivering high-level strategy.

This Role Is NOT a Fit If:

• You have only managed operations for large corporations, enterprise divisions, or boards of directors—if you haven\'t worked directly with the actual owner/founder of a small-to-mid-sized business, you will struggle here.
• You prefer large corporate environments with pre-built, established infrastructure.
• You focus primarily on strategy and want to hand off the actual execution to someone else.
• You lack direct experience advising, coaching, or partnering closely with business owners.

Benefits & Perks

• Unmatched Professional Variety: Transform dozens of entrepreneurial businesses simultaneously instead of optimizing just one.
• High-Agency Culture: We value results over red tape. No micromanagement or useless meetings—just absolute autonomy to deliver world-class operational breakthroughs.
• Leveraged Compensation: A competitive $110,000 base salary with a performance incentive structure bringing total earning potential to $182,000+, scaling directly with the growth you create.

If you’re tired of managing corporate red tape and ready to actually build something that matters, hit apply. Let’s see what you’ve got.