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.
About Four Technologies
Four Technologies is a rapidly growing financial technology company founded in 2018, offering Buy Now, Pay Later (BNPL) solutions. Our platform enables shoppers to split purchases into four interest‑free installments while helping retailers drive higher conversion, larger average order values, and stronger revenue growth. Learn more at paywithfour.com.
About the Role
We are looking for a Senior Director of Marketing Engineering to own and operate Four’s marketing function end‑to‑end, including paid acquisition, organic growth, brand, and content. This role is powered by AI agents and automation and is designed for someone who thrives on leverage, experimentation, and ownership.
You will start as the marketing team, building AI‑driven workflows that produce the output of a much larger organization. As you demonstrate what is possible and push the limits of AI‑first marketing, the team will grow around you—but only after you have maximized the leverage that modern automation makes possible.
This is not a traditional marketing role. You will not rely on outside agencies or third‑party vendors. You will own strategy, systems, execution, creative, campaigns, and measurement yourself. At Four, we believe the future of marketing belongs to people who can think like strategists, create like artists, and build like engineers.
This is a fully remote role with Eastern U.S. time zone alignment required. Miami‑based is a plus but not required. Periodic travel to Miami, FL and Draper, UT is expected for planning and key events.
What You’ll Do
Marketing Strategy & Growth
Own Four’s marketing strategy across acquisition, retention, brand, and revenue growth
Define target audiences, customer segments, and lifecycle journeys using behavioral and performance data
Set and manage marketing budgets, forecasting spend against acquisition targets and ROAS goals
Develop and maintain a marketing roadmap aligned with company priorities
Partner with cross‑functional leaders to translate business objectives into measurable marketing initiatives
Own Four’s presence in AI‑powered discovery so that when consumers ask LLMs about BNPL options, Four is the first and best answer
Paid Acquisition & Performance Marketing
Plan, execute, and optimize paid campaigns across Meta, Google, TikTok, Apple Search Ads, and emerging channels
Build and manage AI‑driven workflows for bidding, targeting, and creative optimization
Own attribution modeling and marketing analytics to understand performance drivers
Monitor and improve key metrics including CAC, ROAS, conversion rates, and funnel efficiency
Test new channels and tactics aggressively, scaling what works and cutting what does not
Content, Creative & Brand
Create compelling content across social, video, email, landing pages, app store assets, and more
Build and maintain Four’s brand voice and visual identity across all touchpoints
Design content strategies that enable rapid learning, iteration, and sustained relevance
Manage social media presence with a focus on engagement and community building
Produce content that resonates with shoppers seeking a smarter, more transparent way to pay
AI‑Powered Marketing Operations
Architect AI agent workflows that automate content creation, campaign management, audience segmentation, reporting, and competitive intelligence
Use and extend Four’s internal AI operating system to capture marketing knowledge and performance insights
Build dashboards and automated reporting for real‑time visibility into results
Evaluate and adopt emerging AI marketing tools and platforms
Document workflows and learnings so the marketing system compounds over time
Compliance & Regulatory Partnership
Partner closely with Compliance and Legal to ensure all marketing activities meet regulatory requirements
Understand the regulatory landscape for BNPL and consumer financial products
Embed compliance review directly into marketing workflows
Maintain auditable records of marketing approvals and reviews
What You’ll Bring
Experience & Technical Skills
15+ years of experience in marketing with ownership of both paid and organic strategies
Proven success operating as a full‑stack marketer in a lean or early‑stage environment
Strong ability to source, analyze, and act on data independently
Hands‑on experience with Meta Ads Manager, Google Ads, and TikTok Ads
Demonstrated strength in creative development with a portfolio of written or visual work
Advanced use of AI tools for content creation, automation, and analysis
Comfort working with modern technology tools such as Git, Jira, and Slack
Experience in fintech, financial services, or regulated industries strongly preferred
Leadership & Working Style
Results‑oriented mindset with a drive to outperform targets
Equal comfort with creative thinking and analytical rigor
Self‑directed, resourceful, and comfortable owning outcomes end‑to‑end
Strong written and verbal communication skills
Excellent project management and prioritization skills
High integrity and attention to detail, especially in regulated environments
Curious, experimental, and continuously improvement‑oriented
Commitment & Availability
Eastern time zone alignment required
Comfortable operating in a fast‑paced, high‑growth environment
Willingness to travel periodically for planning and team collaboration
We Offer
Competitive compensation
Opportunity for leadership growth
Medical, dental, vision, and life insurance
Paid parental leave
Company‑matched 401(k)
Paid time off, holidays, and volunteer hours
Employee resource groups
Employee stock purchase program
Tuition reimbursement
Charitable gift matching
Required job equipment and services
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.