Director, Creative (Remote)

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 Creative Director to lead the creative vision and execution across Progressive Leasing, Purchasing Power, and Money.app, ensuring cohesive, high‑performing, and on‑brand creative across all marketing channels.

This role operates within the broader PROG Holdings ecosystem and plays a critical leadership role during a period of transformation, including the integration of Purchasing Power into the portfolio. The Creative Director will drive strategic, conversion‑focused creative that fuels business growth, customer engagement, and brand evolution—while honoring the unique identity of each brand.

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

WE ARE: A growth‑focused, data‑driven organization committed to building powerful brands and meaningful customer experiences. We believe creativity should be grounded in strategy, informed by performance, and executed with excellence. We value collaboration, accountability, and innovation and we empower our leaders to shape the future of our brands during moments of transformation and growth.

YOU ARE: A strategic, performance‑minded creative leader with a strong point of view and a proven ability to inspire teams. You thrive in multi‑brand environments, balance brand storytelling with conversion‑driven execution, and confidently lead through change. You are equally comfortable partnering with executive leadership as you are mentoring creative talent and rolling up your sleeves to bring ideas to life.

YOUR DAY‑TO‑DAY:

• Lead and define the overarching creative vision across Progressive Leasing, Purchasing Power, and Money.app, spanning all marketing channels including email, paid media, social, web, app experiences, SMS, direct mail, video, in‑store collateral, and emerging platforms

• Develop, maintain, and evolve brand standards and visual guidelines to ensure consistency while allowing for brand differentiation

• Partner closely with Marketing, Growth, CRM, E‑commerce, Product, Merchandising, Analytics, Compliance, and Executive Leadership to translate business objectives into compelling creative strategies

• Oversee the development and delivery of creative assets for lifecycle marketing, acquisition campaigns, paid media, social content, websites, landing pages, sales enablement materials, and internal communications

• Ensure creative deliverables are completed on time, on budget, and aligned with campaign goals and performance targets

• Build, mentor, and lead a high‑performing creative team, including designers, copywriters, content strategists, and external agency partners

• Establish and optimize creative workflows, intake processes, briefing standards, and production timelines to improve efficiency and quality

• Guide concept development from ideation through execution, ensuring strong storytelling, clear value propositions, and performance‑driven design

• Partner with Analytics and Growth teams to implement creative testing frameworks that improve engagement, conversion, and return on ad spend

• Manage relationships with agencies, freelancers, production vendors, and technology partners to scale creative output as needed

• Support brand integration efforts as Purchasing Power transitions into the PROG Holdings ecosystem, aligning messaging and customer experience while honoring brand equity

• Lead rebranding or refresh initiatives tied to campaign launches, seasonal promotions, and major business milestones

• Ensure all creative output meets legal, regulatory, and brand governance requirements

YOU’LL BRING:

• Bachelor’s degree in Marketing, Advertising, Design, Communications, or a related field (Master’s degree a plus)

• 10+ years of progressive creative leadership experience, preferably within performance marketing, fintech, ecommerce, retail, or consumer financial services

• Proven experience leading creative teams through organizational change, merger, acquisition, or brand integration

• A strong portfolio showcasing digital marketing, email, paid media, social campaigns, brand storytelling, and performance‑focused creative

• Experience managing multi‑brand environments while maintaining distinct brand voices

• Deep understanding of customer lifecycle marketing, acquisition funnels, and conversion optimization

• Strong project management and operational discipline with the ability to manage multiple high‑priority initiatives

• Experience collaborating cross‑functionally with Product, Data, Technology, Compliance, and Executive Leadership

• Proficiency with modern creative and marketing technology platforms, including design tools, CMS platforms, marketing automation, and project management software

• Exceptional communication, presentation, and stakeholder management skills

WE OFFER:

• Competitive Compensation

• Full Health Benefits; Medical, Dental, Vision, Life Insurance, and Paid Parental Leave

• Company‑Matched 401(k)

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

• Employee Stock Purchase Program

• Tuition Reimbursement

• Charitable Gift Matching

• Diversity Alliance Resource Groups

• Job‑Required Equipment and Services Provided

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.