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Chief of Staff - Test Assure - Brydon Portfolio Company image - Rise Careers
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Chief of Staff - Test Assure - 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

Average salary estimate

$105000 / YEARLY (est.)
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$90000K
$120000K

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What You Should Know About Chief of Staff - Test Assure - Brydon Portfolio Company, The Brydon Group

Are you ready to take the lead in a dynamic and fast-paced environment? Test Assure, now part of Brydon Portfolio Company, is on the lookout for an exceptional Chief of Staff to join our leadership team. In this pivotal role, you'll be right next to our CEO, helping shape the company's strategic vision while enhancing operational effectiveness across the board. As the Chief of Staff, your insights will drive crucial growth initiatives and ensure seamless communication across departments. You’ll be playing a key role in executing the company’s goals by identifying opportunities and developing actionable plans. Your talent for influencing and collaboration will foster a high-performance culture and inspire our team to aim higher. You bring a wealth of experience from private equity, investment banking, or consulting in a high-growth software company, allowing you to pivot effectively from strategic leadership to hands-on support. At Test Assure, we believe in investing in our high-performing individuals, providing them with invaluable growth experiences within our Chief of Staff network. Join us to drive meaningful impact on a global scale, streamline operations, and be part of a company that is transforming payroll testing for enterprise organizations! If you're curious, efficient, and thrive in a collaborative environment, we can’t wait for you to be part of our team!

Frequently Asked Questions (FAQs) for Chief of Staff - Test Assure - Brydon Portfolio Company Role at The Brydon Group
What are the responsibilities of the Chief of Staff at Test Assure?

As the Chief of Staff at Test Assure, your primary responsibilities include collaborating closely with the CEO to execute the company's strategic vision, driving operational efficiencies, and serving as a liaison between the leadership team. You’ll also monitor performance using key metrics, assist in financial oversight, and prepare essential presentations and communication for various meetings. Your role is crucial in aligning efforts across departments to ensure we collectively reach our strategic goals.

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What qualifications does Test Assure look for in a Chief of Staff?

Test Assure seeks candidates for the Chief of Staff position with at least 3 years of experience in private equity, investment banking, or consulting, preferably in a high-growth software company. A Bachelor’s degree in business or related fields is required, alongside strong management, analytical, and problem-solving skills. Excellent communication abilities and the flexibility to thrive in a fast-paced environment are also essential.

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How does the Chief of Staff at Test Assure support the CEO?

The Chief of Staff at Test Assure plays a vital role in supporting the CEO by facilitating effective communication across the leadership team and ensuring alignment of goals and initiatives. This includes running key team meetings, preparing for board discussions, and providing insights on performance and strategic matters to help inform the CEO’s decisions.

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What is the work culture like at Test Assure for the Chief of Staff role?

The work culture at Test Assure is fast-paced and entrepreneurial, emphasizing collaboration and high performance. As a Chief of Staff, you’ll be encouraged to take initiative, propose solutions to challenges, and work alongside a team that values innovative thinking and execution. Your role will be key in creating an environment that fosters growth and excellence.

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What opportunities for career advancement are available for a Chief of Staff at Test Assure?

At Test Assure, a significant opportunity for career advancement exists for the Chief of Staff position. Typically, individuals spend a minimum of two years at a portfolio company, after which they may choose to pursue various roles, whether at the same company, another Brydon portfolio company, or take part in the CEO-in-Residence cohort, helping them grow their careers meaningfully.

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Common Interview Questions for Chief of Staff - Test Assure - Brydon Portfolio Company
How do you prioritize multiple projects as Chief of Staff?

In prioritizing multiple projects, it's essential to align them with the organization's strategic goals. You'll want to assess their impact on business objectives and communicate with key stakeholders to understand their needs. Effective prioritization often requires daily check-ins and flexibility as new tasks arise, ensuring you're always working on what drives the most value for the company.

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Can you provide an example of how you've improved operational efficiency?

Certainly! A great approach is to use data analytics to assess performance metrics prior to identifying bottlenecks in operations. For example, streamlining a reporting process can save time and increase accuracy. Share specific methods you implemented to improve those processes, including the tools you used and how your actions led to measurable improvements.

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What is your experience in strategic planning?

When discussing your experience in strategic planning, highlight any roles where you contributed to roadmap development and execution. Mention the frameworks or methodologies you are familiar with, and provide examples of initiatives you led, emphasizing the collaboration with cross-functional teams and the quantitative impact of those strategic plans.

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How do you ensure effective communication across departments?

Ensuring effective communication across departments requires establishing regular check-ins and a clear reporting structure. I often utilize collaborative tools to foster transparency and maintain an open-door policy to encourage dialogue. You should advocate for combined meetings or workshops where teams can share updates, fostering collaboration and alignment.

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What metrics do you use to gauge success in your role?

In the Chief of Staff role, key performance indicators related to organizational goals are vital. Examples include financial dashboards, project completion rates, and employee engagement scores. Discuss how you set these KPIs, assess progress, and adjust strategies as necessary to ensure the organization stays on track towards its strategic objectives.

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How do you handle conflicts within the leadership team?

Handling conflicts requires strong diplomacy skills. It's about facilitating honest discussions, actively listening to all parties involved, and striving for a resolution that aligns with the company’s objectives. Describe a situation where you successfully mediated a conflict, illustrating how you helped find common ground and reach a mutually beneficial solution.

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Why do you want to become the Chief of Staff for Test Assure?

Express your passion for Test Assure’s mission and strategic vision. Talk about how your experience aligns with the responsibilities of the Chief of Staff position and how you can contribute to the team’s success. Make sure to convey your enthusiasm for the opportunity to grow with a company that emphasizes innovation and high performance in the software testing industry.

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How do you measure and analyze the performance of different departments?

When measuring departmental performance, I prioritize developing a set of tailored KPIs that reflect the specific objectives of each department. Regularly reviewing these metrics allows for quick differentiation of trends and issues. Be sure to include your experience in providing insights to leadership that inform strategic decision-making based on those analyses.

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Describe a time you had to pivot from a strategic plan.

Discuss how flexibility is essential in today’s dynamic environment. Provide a specific example where you had to alter a strategic initiative due to unforeseen circumstances, how you communicated the change to the team, and what lessons were learned from the experience. Highlight the importance of agility in leadership roles.

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What actions do you take to build relationships at all levels of an organization?

Building relationships requires active engagement and intentional communication. I prioritize one-on-one meetings to understand team members’ perspectives and challenges, offering assistance where needed. Activities such as team-building exercises and informal gatherings also promote relationship building, creating a collaborative and supportive workplace culture.

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Combining the best of private equity and entrepreneurship through acquisition. The Brydon Group partners with entrepreneurs to acquire small businesses in a highly inefficient part of the market.

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DATE POSTED
April 10, 2025

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