Chief of Staff

About Us:

Perpay is a certified B Corp and Philadelphia’s most impactful growth-stage startup. We are driven by a mission to significantly improve the financial stability of everyday Americans. For the past decade, we have established strong product-market fit and a profitable, efficient operating model across a suite of products, positioning Perpay as the premier financial partner for consumers with subprime credit.

With over 500,000 customers who have utilized more than $1 billion in spending power, we are at a pivotal moment. We are scaling our operations, building new offerings, and deepening our impact. We are looking for teammates eager to join us on this journey.

Our venture partners include First Round Capital and L Catterton.

Products we’ve built to make an impact:

• Perpay Marketplace: Combines interest-free payments and modern e-commerce to reduce cost of ownership and promote healthy repayment behavior.
• Perpay+: Leverages Marketplace repayment history to help members monitor and build credit with all 3 credit bureaus.
• Perpay Credit Card: Expands access to the flexibility and benefits of a World Mastercard by removing common barriers like high security deposits and low approval odds.

Our team thrives on in-person collaboration, operating from our unique center-city Philadelphia office. This comfortable "home away from home" space offers river views and fosters rapid product development, strong relationships, and career growth. The energy from achieving big wins is palpable here. While we primarily work in the office, we offer sensible flexibility for personal needs, such as sick children or urgent errands, and coordinate official remote weeks around major holidays. If you are passionate about a meaningful mission, collaboration, equity, and generous perks, Perpay is the best place to be in Philadelphia right now.

About the Role

This is a rare opportunity to work at the center of a high-growth fintech company, reporting to the Office of the CEO and working closely with the leadership team. The role offers unmatched exposure to how decisions get made, how priorities are set, and how a business is actually run.

As Chief of Staff, you will help keep the CEO and leadership team organized, informed, and focused on the company’s most important priorities. The role blends coordination, execution, and problem solving. Some days will involve preparing materials for leadership or board meetings, managing the CEO’s schedule and priorities, or ensuring key follow-ups happen. Other days will involve digging into an ad hoc project, helping pressure-test an idea, or supporting an initiative that moves the business forward.

This role is ideal for someone who is intensely curious, highly organized, and excited by ambiguity. You will be trusted with real responsibility, given visibility few roles offer, and pushed to grow quickly.

Responsibilities

• Be a thought partner and strategic advisor to the Office of the CEO by driving collaboration, challenging ideas, offering different perspectives, and enabling individual and collective growth
• Act as a force multiplier for the Office of the CEO by unlocking the team from day-to-day operations, driving collateral creation, preparing meeting agendas, and coordinating action item execution
• Lead and run with ad hoc projects by jumping into ambiguous problems and driving initiatives from concept through execution
• Identify gaps, risks, and opportunities across the business by staying close to leadership priorities and proactively bringing thoughtful solutions forward
• Act as connective tissue across leadership by sharing context, coordinating communication, and ensuring the right information reaches the right people at the right time

What You’ll Bring

• 4-6 years of experience in highly operational or analytical roles
• Strong judgement and curiosity with a desire to understand why things work, not just what is happening
• Excellent written and verbal communication skills with the ability to distill complexity into clear, concise insights
• Exceptional organization and follow-through with the ability to manage multiple work streams at once
• Comfort operating in fast-moving, unstructured environments with a bias toward action
• High integrity and discretion with the ability to handle sensitive information and high-stakes conversations
• Analytical thinking and comfort breaking down ambiguous problems and forming independent perspectives
• Low ego and high ownership with a willingness to do whatever it takes to move the business forward
• A genuine desire to learn how to run a company and build toward future leadership roles

Hey, we know not everybody checks all the boxes, so if you’re interested, please apply because you could be just what we’re looking for!

What We’ll Bring to Full-time Team Members:

• Meaningful compensation and equity
• Premium medical benefits (fully paid base plan, and very reasonable premium for the buy-up option)
• 4% employer 401k match
• Unlimited PTO policy
• ​​Remote weeks around major holidays + extra holiday on weekends like MDW and LDW
• High quality catered lunch by local chefs, 4 days / week
• Gym subsidy
• Paid cell phone + plan
• Student loan repayment program
• Relocation assistance
• Generous team member discounts

This is not a remote opportunity; it is 100% onsite (#LI-Onsite) (#LI-TH1) (#LI-AK1)

Perpay is proud to be an equal opportunity employer. We value diversity in all its forms and are committed to creating an inclusive environment. We do not discriminate on the basis of race, religion, color, national origin, gender identity, sexual orientation, sex (including pregnancy), marital status, political affiliation, age, veteran status, disability status or other non-merit factor. Please contact us at careers@perpay.com to request accommodation.