Chief of Staff

Perpay - Career's Page

$90K — $130K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 4-6 years in operational or analytical roles
  • Strong judgement with curiosity to understand underlying dynamics
  • Excellent written and verbal communication skills for simplifying complexity
  • Exceptional organization and ability to manage multiple projects
  • Comfortable in fast-paced, unstructured settings with proactive action
  • High integrity with discretion for handling sensitive information
  • Analytical thinker comfortable with ambiguity and independent perspectives
  • Low ego and high ownership mindset, willing to help wherever needed
  • Desire for learning to run a company and move into leadership roles

Responsibilities

  • Serve as a strategic advisor to the CEO, fostering collaboration and challenging ideas
  • Enhance the CEO's efficiency by managing day-to-day operations and ensuring follow-ups occur
  • Lead ad hoc projects from their inception through execution
  • Identify business gaps and opportunities by aligning with leadership priorities
  • Facilitate effective communication among leadership teams by sharing relevant insights

Benefits

  • Meaningful compensation and equity
  • Premium medical benefits with manageable premiums
  • 4% employer 401k match
  • Unlimited PTO policy
  • Remote weeks around major holidays
  • High quality catered lunches 4 days a week
  • Gym subsidy included
  • Paid cell phone and plan
  • Student loan repayment assistance
  • Relocation support available
  • Generous employee discounts
Full Job Description
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)

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