Chief of Staff - TestAssure - Brydon Portfolio Company

About the Role:

TestAssure, acquired by Brydon in April 2025, is seeking an exceptional Chief of Staff to join our leadership team and play a crucial role in supporting the company’s strategic vision. As the Chief of Staff to the CEO, you will have broad visibility across the organization, enabling company strategy, leading strategic growth initiatives, facilitating communication across departments, and supporting operational effectiveness. You will be a key advisor, collaborator, and executor, working closely with the CEO to align organizational priorities, streamline operations, and foster a culture of high performance. You will have significant exposure and opportunity to drive impact across TestAssure on a global basis.

The right individual will thrive in a fast-paced, entrepreneurial environment and possess the versatility to drive key projects both independently and in partnership with key stakeholders. They will proactively identify challenges and opportunities, translating strategic conversations into actionable roadmaps. They will be curious, efficient, and possess a high drive for excellence.

Alongside your leadership experience at TestAssure, you will be part of Brydon’s Chief of Staff network – with access to peers, tools & resources, and ongoing professional development. Small business acceleration is fundamentally about talent and execution, and Brydon invests significantly in providing meaningful growth experiences to high-performing individuals.

About the Business:

TestAssure provides modern, automated payroll testing to enterprise organizations. TestAssure gives their customers the confidence to test quickly, extensively, and go-live sooner. With a smooth testing experience provided by TestAssure, customers can stay on track with their implementation of their new workforce management solutions, and maintain pay compliance as their workforce management system is upgraded, laws change, and the business changes.

Core Responsibilities:

Strategy Leadership:

• Collaborate with the CEO to execute and advance the company's strategic vision, ensuring alignment across departments and functions.
• Translate the vision into actionable plans, initiatives, and metrics, and communicate that vision to the company and externally as needed.
• Lead the annual strategic planning process along with the CEO and members of the management team.
• Drive operational efficiency in line with strategic goals by identifying areas for improvement, implementing best practices, and optimizing processes to enhance productivity and profitability.

Cross-Functional Collaboration:

• Serve as a liaison between the CEO and the leadership team, fostering effective communication and alignment of goals and initiatives.
• Work closely with the entire leadership team to ensure alignment and drive key initiatives.

Performance Monitoring:

• Establish key performance indicators (KPIs) and metrics to track progress against strategic objectives, identify trends and opportunities across sales, marketing and financial performance and provide insights to the CEO and leadership team.

Financial Performance Oversight:

• Directly assist with key FP&A analysis to ensure alignment of financial goals with overall business objectives and monitor financial performance, including closing the books, budgeting, forecasting, and financial analysis.
• Provide insights and recommendations based on financial data to support strategic decision-making.

Leadership Support:

• Provide direct support to the CEO, including preparing for and running key team and cross-functional meetings such as leadership meetings, monthly business reviews, board meetings, and occasional off-sites/on-sites.
• Prepare compelling presentations and memos, ensuring clear and effective communication across all levels of the company.

Qualifications:

• 3+ years of work experience in private equity, investment banking, consulting and/or a PE or VC-backed high growth software company
• Bachelor’s degree in business or a related field
• Proven ability to adapt to various levels of responsibilities with ability to quickly pivot from executive leadership to tactical partnership and support of front-line staff.
• Strong management skills with the ability to lead multiple high-priority projects simultaneously across different vertical teams (e.g. experience in consulting or investment banking).
• Excellent communication and interpersonal skills, with the ability to build relationships and influence at all levels of the organization.
• High level of analytical and problem-solving skills, with a track record of translating strategic conversations into actionable plans.
• Ability to thrive in a fast-paced, dynamic environment, and adapt to evolving priorities.

Location:

• Flexible, but employee will need to work east coast hours. Opportunity for hybrid work environment if candidate is in Dallas, Boston, Nashville or Washington, DC..

Compensation & Career Path:

• This is a full-time salary position and is eligible for benefits including health insurance, access to 401K, and paid time off. Compensation will depend on experience.
• Brydon Chiefs of Staff typically spend a minimum of 2 years at a portfolio company (ideally longer - this is not a "rotational" role), after which time they may decide to pursue a different role at that company, pursue a role at a different portfolio company, or apply to our next CEO-in-Residence cohort