Chief of Staff to the Chief Executive Officer (CEO)

About the Company

Successful provider of cloud-based financial software for K-12 public schools

Industry
Computer Software

Type
Privately Held, Private Equity-backed

Founded
1996

Employees
201-500

Categories

- Information Technology & Services
- Technology
- SAAS
- B2B
- Accounting
- Finance
- Financial Services
- Payments
- Software
- Financial Transactions
- Clearinghouse
- Insurance

Specialties

- school activity fund software
- school accounting software
- fund management software
- and school online payment software

About the Role

The Company is seeking a Chief of Staff to the CEO to play a pivotal role in the executive team's strategic and operational alignment. The successful candidate will be responsible for turning the CEO's priorities into company-wide objectives, tracking their progress, and leading the quarterly reset process.

This senior operating role demands a skilled with 8-12 years' experience, including a minimum of 3 years in an operating capacity, and a proven track record in a B2B SaaS, fintech, or payments environment. The Chief of Staff will also be involved in executive cadence, board and governance activities,



and will lead strategic projects and M&A; coordination.

The ideal candidate will have a background in strategy consulting, investment banking, or corporate development, and possess the ability to influence without authority, demonstrate clear thinking and writing, and exhibit commercial and financial fluency.

The role requires a candidate with a strong foundation in operating rigor, discretion, and judgment, and a low ego, high ownership mentality. Experience in education technology or the public sector, bilingual proficiency in English and French, and an MBA or equivalent are considered advantageous. The Chief of Staff will work closely with the CEO, CFO, and other executives, and will be measured on their ability to close commitments on time, lead strategic projects, and improve the decision-making process within the executive team. The position is not for a bottleneck; the Chief of Staff will be expected to lead without becoming a hindrance, and to ensure that the executive team operates with a predictable and efficient rhythm.

Hiring Manager Title
CEO

Functions

- General Management
- Strategy
- Operations

📌 Chief of Staff to the Chief Executive Officer (Toronto)
🏢 Nameless
📍 Toronto