Director, Operations Sales Strategy And Execution - Remote Eligible

Director, Operations Sales Strategy And Execution

The Director, Operations Sales Strategy and Execution is responsible for defining, executing, and continuously improving Assurant's cross-sell and upsell sales strategy across U.S. Connected Living Operations. They will lead the creation, deployment, and scaling of revenue-generating programs embedded within claims, service, trade-in, upgrade, and technical support customer journeys across phone, chat, and digital channels.

The role owns contact center sales enablement, agent incentive and compensation programs, AI-assisted selling capabilities, and cross-channel execution, ensuring programs drive incremental revenue while protecting customer experience, client commitments, and regulatory compliance.

What will be my duties and responsibilities in this job?

Cross-Sell & Upsell Sales Strategy

• Establish and communicate the strategic vision for cross-sell and upsell programs across Connected Living.
• Identify priority customer moments, product pairings, and value-added offers aligned to customer needs and client objectives.
• Define monetization frameworks that balance revenue growth, customer experience, compliance, and operational scalability.
• Partner with Product, Marketing, Digital, Legal, and Compliance teams to ensure offers are differentiated, compliant, and scalable.
• Develop multi-year roadmaps to expand sales motions across assisted and digital channels.

Program Design, Execution & Optimization

• Design, launch, and scale agent-assisted and digital sales programs embedded within claims and service journeys.
• Own pilot design, test-and-learn execution, phased rollouts, and continuous optimization of initiatives.
• Ensure sales motions integrate seamlessly into operational workflows without degrading service performance.
• Standardize operating models, governance, and controls to support multi-LOB scalability.

Contact Center Incentives, Enablement & AI Tools

• Design, implement, and govern contact center agent incentive and compensation programs tied to cross-sell and upsell performance.
• Define sales KPIs, conversion targets, and incentive mechanics aligned to desired behaviors and CX outcomes.
• Own performance reporting and ongoing optimization of incentive effectiveness.
• Lead implementation and continuous improvement of AI Agent Assist and AI-driven sales enablement tools, including offer recommendations, scripting support, eligibility logic, and next-best-action guidance.
• Partner with Training, Quality, Workforce, and Technology teams to ensure agent readiness, adoption, and sustained performance.

Performance Management, Reporting & Analytics

• Own sales performance dashboards, executive-level reporting, and client-facing results readouts.
• Partner with Analytics teams to identify performance drivers, root causes, and optimization opportunities.
• Track revenue, ROI, customer experience impact, compliance outcomes, and operational tradeoffs.
• Use data to refine targeting, offers, channel mix, and timing.

Leadership, Stakeholder Management & Governance

• Lead and develop a high-performing team responsible for sales strategy, execution, and optimization.
• Serve as the primary point of accountability for cross-sell and upsell initiatives across Connected Living.
• Partner closely with Operations, Product, Digital, Client Management, Legal, and Compliance leaders.
• Support client discussions by articulating program value, performance results, and future growth opportunities.

What are the requirements needed for this position?

• Bachelor's degree or equivalent experience
• 8+ years of experience in inside sales, contact center sales, or revenue growth roles
• 5+ years leading sales programs in a B2B2C environment
• Demonstrated experience embedding sales motions into service, claims, or support interactions
• Strong understanding of contact center operations, digital customer journeys, and CX metrics
• Proven ability to design scalable sales programs and lead execution across multiple channels
• Exceptional stakeholder management and executive communication skills
• Strong analytical mindset with experience using data to drive sales performance improvements
• Ability to lead through influence in complex, matrixed organizations
• High ownership, accountability, and bias for action
• Experience in insurance, warranty, protection, telecom, retail services, or device lifecycle programs preferred
• Experience selling value added services during claims or support interactions a plus

Pay Range: $103,800.00 - $173,300.00

If there is no posting end date listed then this is a pipeline requisition, and we will continue to collect applications on an ongoing basis.