Remote Title Insurance Attorney Jobs in Kentucky

Job Title: Head of Sales Operations & Enablement

Reports to: Chief Distribution Officer

Direct reports: Sales Technology Administrator, Sales Enablement & Trainer

Location: Remote or Louisville, KY preferred

POSITION OVERVIEW

The Head of Sales Operations & Enablement serves as the operational backbone of the revenue organization and Chief of Staff to the Head of Sales. This is a critical backfill hire responsible for building and maintaining the processes, systems, and infrastructure that allow the sales organization to scale - while managing leadership through KPIs and operational cadence.

This role is designed for a builder. The ideal candidate has thrived in smaller, entrepreneurial company environments where they have created structure, process, and operational discipline from scratch. Candidates who have only operated inside large, structured organizations will not succeed here.

WHAT YOU WILL OWN

Sales Operations & Process

• Build and maintain the sales operating rhythm - QBRs, pipeline reviews, forecast cadence, and field accountability structures
• Own CRM governance, pipeline stage discipline, and process compliance across the sales organization
• Drive consistency in sales execution across regions and advisor-facing teams
• Identify and eliminate operational bottlenecks that slow advisor productivity and revenue execution
• Partner with leadership on territory planning, headcount modeling, and capacity planning

Chief of Staff - Leadership Management Through KPIs

• Serve as Chief of Staff to the Head of Sales, owning the operational cadence that keeps leadership aligned and accountable
• Build and maintain the KPI dashboards and reporting infrastructure that allow the sales leader to manage the business by the numbers
• Run the leadership operating calendar - agenda management, cross-functional alignment, strategic project execution, and meeting discipline
• Act as proxy for the Head of Sales on operational and cross-functional matters
• Ensure leadership has clean, timely visibility into pipeline, production, advisor activity, and team performance

Sales Enablement Strategy

• Develop and execute the sales enablement strategy across onboarding, continuous learning, and field readiness
• Build and iterate on training programs covering products, positioning, systems, and sales methodology
• Partner with Sales Enablement & Trainer on program design and execution
• Align field messaging with marketing and product through launch readiness programs

Cross-Functional Coordination

• Serve as the central operational liaison between Sales, Marketing, Product, Operations, Compliance, and Technology
• Lead cross-functional initiative coordination and ensure field readiness on all product and process launches
• Own sales communications strategy and internal field engagement

WHAT WE ARE LOOKING FOR

Required

• 7–12+ years in Sales Operations, Revenue Operations, Sales Enablement, or Commercial Strategy
• Demonstrated experience thriving in a small company or early-stage growth environment - this is non-negotiable
• Proven ability to build sales process, forecasting infrastructure, and KPI frameworks from the ground up
• Strong CRM and sales technology expertise; Salesforce experience strongly preferred
• Executive presence and communication skills - comfortable presenting to and managing senior leadership
• Strong analytical mindset combined with hands-on execution capability

Preferred

• Financial services, fintech, insurance, wealth management, or advisor distribution experience
• Experience serving in a Chief of Staff, Head of RevOps, or VP Sales Operations capacity
• Familiarity with Salesloft, Gong, and ZoomInfo ecosystems
• Track record managing KPI governance and leadership accountability structures

The right candidate can point to a specific company where they joined with minimal structure and built the operational foundation that allowed the sales organization to scale.

COMPENSATION

Competitive base salary and performance bonus. Compensation commensurate with experience.