Job Description
Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. As an almost 20+ year old FinTech company that has gone from start-up to industry leader, we know how to innovate, simplify, and value all people. We are a company founded on our grit and we are constantly looking to the future. As an ever-evolving group of entrepreneurs and technologists, we strive to do the right thing period in all aspects of our work. We are a subsidiary of PROG Holdings (NYSE: PRG), an exciting FinTech holding company, with three business segments including Progressive, Vive Financial, and Four, a Buy Now Pay Later (BNPL) platform.
Four Technologies is a fast‑growing, Miami‑based fintech company offering Buy Now, Pay Later (BNPL) solutions that help shoppers split purchases into four interest‑free payments while driving higher conversion, larger basket sizes, and stronger revenue for retailers. Founded in 2018, Four continues to scale quickly as demand for flexible payment options accelerates.
Learn more at paywithfour.com.
We’re hiring a strategic, AI‑forward Controller who will be a PROG Leasing employee supporting the FOUR business. In this role, you’ll report to PROG’s Principal Accounting Officer while partnering day‑to‑day with the President of Four and the Four leadership team. You’ll help build the financial infrastructure that enables Four’s next stage of growth—ensuring accuracy, operational rigor, and scalable processes in a high‑volume, fast‑moving environment.
This isn’t a traditional Controller role. You’ll be hands‑on with complex revenue operations, embed in strategic discussions, and use AI and automation to modernize how the function operates. You’ll influence margin expansion, decision‑making, and operational efficiency—not just report on the numbers.
This is a hybrid role aligned to Eastern time, with periodic in‑office presence in Miami, FL and periodic travel to Draper, UT.
What You'll Do
Core Accounting & Reporting
• Execute all Controller duties with meticulous accuracy and uncompromising standards
• Own monthly reporting with confidence-inspiring precision
• Prepare and present financial reports to the executive team monthly
• Responsible for maintaining Four’s internal controls over financial reporting, including ensuring the ongoing operating effectiveness of all key controls
• Lead and coordinate all internal and external audit requests, ensuring high-quality, audit-ready support across a fast-moving, lean organization
• Partner with PROG Holdings accounts payable shared service function to ensure accuracy and completeness Four’s monthly operating expenses
• Partner with other PROG Holdings and Four technology functions for continuous process improvement to ensure the highest-quality data and results
• Provide oversight, and hands-on coaching to a lean accounting team of two, setting clear expectations and maintaining high standards
• Oversee Four’s compliance with CECL accounting standards, including governance, methodology oversight, and accurate financial reporting for its provision for credit losses
Strategic Analysis
• Develop performance dashboards and KPIs for operational and executive decision-making
• Embed into strategic discussions on interchange economics, underwriting optimization, loyalty programs, and new revenue streams
• Support margin expansion through modern processes, tooling, and automation
• Stay dialed into all areas of Four to ensure Accounting keeps pace with product, data, and global expansion
Cross-Company Partnership
• Harmonize Four's speed and agility with PROG's standards and rigor
• Build strong relationships across PROG Holdings and connect them to the Four team
• Adopt and translate PROG Accounting standards effectively for Four's context, including the implementation of new accounting policies for changes in Four’s operating model, as needed
• Unify processes between PROG and Four while maintaining Four's operational velocity
• Serve on PROG’s Disclosure Committee to ensure proper disclosures and reporting in all SEC filings
What You'll Bring
Experience & Technical Skills
• 10+ years of experience in accounting/finance leadership, including Controller or Senior Accounting Manager roles
• Direct experience with complex revenue operations at scale on lean teams
• Deep familiarity with DTC economics, revenue flows, marketing attribution, and digital product accounting
• Experience with multi-currency, global accounting requirements
• Comfortable with cloud expense accounting (Azure, AWS, and related infrastructure platforms)
• Strong Power BI experience and data-driven insight generation
• Technology-forward orientation—comfortable with automation, AI, and modern tooling
• Experience preparing for and communicating with Boards of Directors
• Experience working with a modern ERP system, including leveraging the technology to streamline the financial close process
• Bachelor's degree in finance, economics, accounting, or related field
• CPA required
Leadership & Working Style
• High integrity and uncompromising standards—you never accept shortcuts
• Comfortable challenging leadership on day one; equally comfortable being challenged intensely in return
• Coachable and able to act quickly on constructive feedback
• Hungry to learn and improve every day
• Strong communicator using modern collaboration tools (Slack, Confluence)
• Someone the VP of Financial Reporting and President of Four can trust immediately to do the right thing
Commitment & Availability
• Willing to work long hours during critical periods (month-end, quarter-end, audits)
• Eastern time work alignment to maximize collaboration with the Four team
• Comfortable wearing many hats across Finance, Ops, and Analysis
• Able to be in the Miami office at least one week per month (up to three during peak periods)
• Able to be in Draper, Utah at least one week per quarter to maintain PROG alignment and relationships
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, ****** 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.
Four Technologies is a fast‑growing, Miami‑based fintech company offering Buy Now, Pay Later (BNPL) solutions that help shoppers split purchases into four interest‑free payments while driving higher conversion, larger basket sizes, and stronger revenue for retailers. Founded in 2018, Four continues to scale quickly as demand for flexible payment options accelerates.
Learn more at paywithfour.com.
We’re hiring a strategic, AI‑forward Controller who will be a PROG Leasing employee supporting the FOUR business. In this role, you’ll report to PROG’s Principal Accounting Officer while partnering day‑to‑day with the President of Four and the Four leadership team. You’ll help build the financial infrastructure that enables Four’s next stage of growth—ensuring accuracy, operational rigor, and scalable processes in a high‑volume, fast‑moving environment.
This isn’t a traditional Controller role. You’ll be hands‑on with complex revenue operations, embed in strategic discussions, and use AI and automation to modernize how the function operates. You’ll influence margin expansion, decision‑making, and operational efficiency—not just report on the numbers.
This is a hybrid role aligned to Eastern time, with periodic in‑office presence in Miami, FL and periodic travel to Draper, UT.
What You'll Do
Core Accounting & Reporting
• Execute all Controller duties with meticulous accuracy and uncompromising standards
• Own monthly reporting with confidence-inspiring precision
• Prepare and present financial reports to the executive team monthly
• Responsible for maintaining Four’s internal controls over financial reporting, including ensuring the ongoing operating effectiveness of all key controls
• Lead and coordinate all internal and external audit requests, ensuring high-quality, audit-ready support across a fast-moving, lean organization
• Partner with PROG Holdings accounts payable shared service function to ensure accuracy and completeness Four’s monthly operating expenses
• Partner with other PROG Holdings and Four technology functions for continuous process improvement to ensure the highest-quality data and results
• Provide oversight, and hands-on coaching to a lean accounting team of two, setting clear expectations and maintaining high standards
• Oversee Four’s compliance with CECL accounting standards, including governance, methodology oversight, and accurate financial reporting for its provision for credit losses
Strategic Analysis
• Develop performance dashboards and KPIs for operational and executive decision-making
• Embed into strategic discussions on interchange economics, underwriting optimization, loyalty programs, and new revenue streams
• Support margin expansion through modern processes, tooling, and automation
• Stay dialed into all areas of Four to ensure Accounting keeps pace with product, data, and global expansion
Cross-Company Partnership
• Harmonize Four's speed and agility with PROG's standards and rigor
• Build strong relationships across PROG Holdings and connect them to the Four team
• Adopt and translate PROG Accounting standards effectively for Four's context, including the implementation of new accounting policies for changes in Four’s operating model, as needed
• Unify processes between PROG and Four while maintaining Four's operational velocity
• Serve on PROG’s Disclosure Committee to ensure proper disclosures and reporting in all SEC filings
What You'll Bring
Experience & Technical Skills
• 10+ years of experience in accounting/finance leadership, including Controller or Senior Accounting Manager roles
• Direct experience with complex revenue operations at scale on lean teams
• Deep familiarity with DTC economics, revenue flows, marketing attribution, and digital product accounting
• Experience with multi-currency, global accounting requirements
• Comfortable with cloud expense accounting (Azure, AWS, and related infrastructure platforms)
• Strong Power BI experience and data-driven insight generation
• Technology-forward orientation—comfortable with automation, AI, and modern tooling
• Experience preparing for and communicating with Boards of Directors
• Experience working with a modern ERP system, including leveraging the technology to streamline the financial close process
• Bachelor's degree in finance, economics, accounting, or related field
• CPA required
Leadership & Working Style
• High integrity and uncompromising standards—you never accept shortcuts
• Comfortable challenging leadership on day one; equally comfortable being challenged intensely in return
• Coachable and able to act quickly on constructive feedback
• Hungry to learn and improve every day
• Strong communicator using modern collaboration tools (Slack, Confluence)
• Someone the VP of Financial Reporting and President of Four can trust immediately to do the right thing
Commitment & Availability
• Willing to work long hours during critical periods (month-end, quarter-end, audits)
• Eastern time work alignment to maximize collaboration with the Four team
• Comfortable wearing many hats across Finance, Ops, and Analysis
• Able to be in the Miami office at least one week per month (up to three during peak periods)
• Able to be in Draper, Utah at least one week per quarter to maintain PROG alignment and relationships
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, ****** 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.
💡 Quick Summary
Seeking a career-building opportunity? The Controller — FOUR (PROG Leasing) | Hybrid position is now open for candidates interested in the Remote Jobs sector. This role in Miami offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in Remote Jobs is a plus.