Manager – Digital Experience & Web Operations

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. With more than 20 years in FinTech, we’ve grown from start-up to industry leader by innovating, simplifying, and valuing people. We are a subsidiary of PROG Holdings (NYSE: PRG), a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power (a leading employee purchase program for consumer products and services using payroll deduction), and Four, a Buy Now Pay Later (BNPL) platform.

We are currently hiring a Manager, Digital Experience & Web Operations to own the performance and execution of our digital experience across web and mobile app. This role is accountable for how our site converts, merchandises, and scales, supporting both existing customers and new customer acquisition into our lease-to-own ecosystem.

Employee Value Proposition (EVP):PROG is dedicated to providing people with opportunity—opportunity for inclusive collaboration, opportunity for innovation, and opportunity for development.

WE ARE: A fast-growing, customer-focused Direct-to-Consumer (D2C) organization operating at the intersection of Sales, Marketing, Product, Engineering, and Analytics. We are passionate about building high-performing, scalable digital experiences that drive applications, approvals, and partner utilization across our marketplace. Our teams value data-driven decision making, cross-functional partnership, and continuous improvement as we scale our digital ecosystem.

YOU ARE: A strategic and hands-on digital leader who thrives in fast-paced environments and enjoys owning outcomes. You are highly analytical, customer-obsessed, and comfortable operating as a player-coach—setting direction while remaining close to execution. You are confident partnering with senior stakeholders, translating business strategy into on-site execution, and driving impactful improvements across the customer funnel.

YOUR DAY-TO-DAY:

On-Site Experience Performance

• Own site performance across key metrics including conversion, engagement, and revenue.

• Identify and prioritize the highest-impact opportunities to improve the customer funnel.

• Partner with Product to influence roadmap priorities based on business impact and customer needs.

Site Operations & Execution

• Lead day-to-day site operations including publishing, QA, and release coordination.

• Ensure site stability, speed, and a seamless end-to-end user experience.

• Build and scale repeatable processes for content updates, campaigns, and on-site merchandising.

Merchandising & Experience Optimization

• Own how retailers, products, and offers are surfaced and promoted across the site.

• Optimize product discovery across search, navigation, and landing page experiences.

• Oversee product ingestion and ensure data quality across a large, dynamic catalog.

Conversion Rate Optimization & Experimentation

• Build and execute a structured testing and experimentation roadmap.

• Analyze user behavior and funnel performance to identify friction points.

• Partner cross-functionally to implement and scale data-driven improvements.

Demand & Merchandising Integration

• Translate retailer and partner priorities into effective on-site merchandising strategies.

• Leverage consumer demand insights (search behavior and site analytics) to inform navigation, search, and landing experiences.

• Balance business priorities with customer intent to maximize both conversion and partner performance.

Team Leadership & Cross-Functional Partnership

• Lead and develop a small, high-impact team, including Web Producers and Web Merchandisers.

• Operate as a player-coach, setting clear expectations while supporting hands-on execution.

• Partner closely with Marketing, Product, Engineering, Sales, and Analytics to deliver a cohesive on-site experience.

YOU’LL BRING:

• 10+ years of experience in eCommerce, marketplace, or digital operations roles.

• 7+ years of experience leading digital teams in fast-paced environments.

• Proven experience owning or influencing site performance and conversion outcomes.

• Strong background in on-site merchandising, product or retailer discovery, and CRO/experimentation.

• Experience partnering cross-functionally with Sales, Marketing, Product, and Engineering teams.

• Hands-on experience with CMS platforms, eCommerce platforms, product catalogs, and web/mobile apps.

• Strong analytical skills and experience with tools such as Heap, Google Analytics, Adobe Analytics, or similar.

• Nice to have: Experience leveraging AI to optimize digital or business performance.

WE OFFER:

• Competitive Compensation

• Full Health Benefits (Medical, Dental, Vision, Life Insurance)

• Paid Time Off, Paid Holidays, and Paid Volunteer Time

• Company-Matched 401(k)

• Tuition Reimbursement

• Employee Resource & Diversity Groups

• Charitable Gift Matching

• Job-required equipment and services provided

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Progressive Leasing welcomes and encourages diversity in the workplace. We do not discriminate in any aspect of employment on the basis of race, color, religion, national origin, ancestry, gender, sexual orientation, gender identity and/or expression, age, veteran status, disability, or any other characteristic protected by federal, state, or local employment discrimination laws where Progressive Leasing does business.