Senior Director of Marketing Engineering – FOUR (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.

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.