# Chief of Staff

**Company:** [Perpay](https://hotfix.jobs/companies/perpay)
**Location:** Philadelphia, PA
**Role:** Executive Leadership
**Experience:** 4+ years
**Skills:** Strategic Planning, Project Management, Analytical Thinking, Communication Skills, Organizational Skills, Risk Assessment, Stakeholder Coordination, Operational Excellence, Business Analysis
**Posted:** 2026-04-03

> Strategic advisor to the CEO handling operations, ad hoc projects, cross-leadership coordination, and proactive business insights in a fast-paced environment. Requires 4-6 years operational/analytical experience, strong judgment, communication, and organization.

## Job Description

## 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

## 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

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**Canonical:** https://hotfix.jobs/jobs/e7caa845-a40a-4947-887b-2cad3a8e3df3