Chief of Staff

Caseware International - Boston, MA

Full-time - Senior

Hybrid - Boston, MA

10,001+ employees

Professional, Scientific, and Technical Services

About the position

The Chief of Staff at Caseware will serve as a trusted strategic advisor to the CEO and the Executive team, focusing on promoting collaboration and communication across all divisions. This high-impact role is essential for ensuring the execution of strategic priorities, particularly in partnership with investors, and will involve significant interaction with senior leadership and critical business operations.

Responsibilities

• Act as an extension of the CEO in meetings and ensure operational targets are met.
• Prepare the CEO and leadership team for critical internal and external meetings.
• Ensure clear deliverables and effective communication within the Senior Leadership Team (SLT).
• Report on roadmap prioritization and progress, tracking key milestones and metrics.
• Manage critical investments in M&A by creating integration plans and ensuring completion cross-functionally.
• Build and present executive presentations for stakeholders.
• Build trust among executive leaders and advise on key issues and productivity.
• Participate in key client meetings, Board of Directors meetings, and internal strategic planning meetings.

Requirements

• 4-5 years of experience as a management consultant or relevant work experience.
• 3+ years within an organization focused on strategy, operations, and finance (preferred).
• MBA or relevant business experience (preferred).
• Experience working with executive and board levels in tech/software companies or related experience.
• Experience with due diligence through mergers and acquisitions, including integrations.
• Demonstrated ability in gathering, analyzing, and presenting financial plans and forecasts.
• Detail-oriented with strong communication and presentation skills.
• High sense of maturity and urgency with effective prioritization.

Nice-to-haves

• Experience in the audit and accounting software industry.
• Familiarity with financial modeling and business analytics.

Benefits

• Hybrid/remote work options for Greater Toronto or Boston Area residents.
• Support for diversity and inclusion in the workplace.