Chief of Staff
SquarePeg
People & HR, Operations
Boston, MA, USA
Posted on Aug 13, 2025
Who are we?
We are a startup on a mission to make “earning” a built-in feature of everyday finance.
We combine real-time purchase data with our proprietary algorithms to unlock access to earning and savings opportunities for millions of people. We are backed by venture investors on the Midas List, and we plan to disrupt the nearly $1T digital advertising market.
Role
We are seeking a talented and highly motivated Chief of Staff to help us execute on our grand vision - someone who is excited about working across a variety of functions, including but not limited to: product, sales, marketing, and investor management. This is a high impact role for someone who wants visibility into nearly every function of an early-stage company.
This role is ideally suited to a candidate with top-tier consulting, banking, and/or highly relevant startup experience.
You will work with and report directly to the CEO.
The work you’ll do:
We are a startup on a mission to make “earning” a built-in feature of everyday finance.
We combine real-time purchase data with our proprietary algorithms to unlock access to earning and savings opportunities for millions of people. We are backed by venture investors on the Midas List, and we plan to disrupt the nearly $1T digital advertising market.
Role
We are seeking a talented and highly motivated Chief of Staff to help us execute on our grand vision - someone who is excited about working across a variety of functions, including but not limited to: product, sales, marketing, and investor management. This is a high impact role for someone who wants visibility into nearly every function of an early-stage company.
This role is ideally suited to a candidate with top-tier consulting, banking, and/or highly relevant startup experience.
You will work with and report directly to the CEO.
The work you’ll do:
- Drive strategic decision-making alongside the CEO
- Support executive leadership in business development, finance, product, and marketing initiatives
- Prepare materials for investor meetings, board updates, and fundraising rounds (or strategic acquisitions)
- Lead special projects and initiatives from the CEO
- Serve as a trusted advisor to the leadership team by identifying key strategic topics to address, providing insights, analyzing data, and offering objective feedback on key decisions
- 3+ years experience in finance, consulting, or equivalent startup role
- Excellent written and verbal communication skills including development of presentations and financial models
- Strong data analysis capability (SQL) is preferred
- Particularly strong attention to detail and overall level of organization
- Comfortable operating in ambiguity and rolling up your sleeves to get things done
- A strategic problem-solver who can transform nascent ideas into actionable plans and lead cross functional teams
- Full-time and in-person in Boston, MA
- Competitive salary based on experience level
- Meaningful equity package with significant upside potential
- Competitive paid time off
- Monthly wellness stipend for your choice of wellness benefits
- Medical, dental, and vision insurance
