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

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Pay Range:

Any posted pay range considers a wide range of compensation factors, including candidate background, experience and work location, while also allowing for salary growth within the position.

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.

Helping People Thrive in a Connected World
Connect with us. Bring us your best work and your brightest ideas. And we’ll bring you a place where you can thrive. Learn more at jobs.assurant.com.

For U.S. benefit information, visit myassurantbenefits.com. For benefit information outside the U.S., please speak with your recruiter.

What’s the culture like at Assurant?
Our unique culture is a big reason why talented people choose Assurant. Named a Best/Great Place to Work in 14 countries and awarded the Fortune America’s Most Innovative Companies recognition, we bring together top talent around the world. Although we have a wide variety of skills and experiences, we share common characteristics that are uniquely Assurant. A passion for service. An ability to innovate in practical ways. And a willingness to take chances. We call our culture The Assurant Way.

Company Overview
Assurant is a leading global business services company that supports, protects, and connects major consumer purchases. A Fortune 500 company with a presence in 21 countries, Assurant supports the advancement of the connected world by partnering with the world’s leading brands to develop innovative solutions and deliver an enhanced customer experience through mobile device solutions, extended service contracts, vehicle protection services, renters insurance, lender-placed insurance products, and other specialty products.

AI and Biometric Usage

Assurant supports the responsible use of Artificial Intelligence (AI), but we want to know the real you. Visit our AI Usage Guidelines page to understand what we expect from applicants regarding their use of AI during the application process.  

Employment is contingent upon completion of a required identity verification process, which may include biometric technology, where permitted by applicable law and subject to applicable notice and consent requirements. See our Privacy Notice to learn about Assurant’s privacy practices, including our use of AI-enabled technology, automated decision making, and biometric information.

Equal Opportunity Statement
Assurant is an Equal Employment Opportunity employer and does not use or consider race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by federal, state, or local law in employment decisions.

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