Chief of Staff

Job Description

The Chief of Staff serves as the trusted right hand and strategic operator for the Chief Executive Officer, enabling the CEO to operate at the highest level across a newly merged executive team. The role is designed to drive alignment and decision velocity at the top of the organization, keeping priorities focused across leadership and ensuring that the most critical work moves forward with speed, clarity, and accountability.

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This is a high-impact building role. The successful candidate will stand up a sophisticated, mature Chief of Staff / Office of the CEO function for a national organization that is now significantly larger and more complex, designing the operating rhythms, governance, and communication systems that allow the executive team and the broader organization to run with intentionality and transparency.

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Partnering with the leadership responsible for enterprise project management and integration, the Chief of Staff ensures executive-level oversight, visibility, and alignment across the organization’s most important priorities. The focus of the role is the CEO’s operating model, executive governance, change leadership, and enabling continued organic growth. The successful candidate will balance strategic thinking with hands-on execution, moving fluidly between the highly strategic and the operationally precise, and will be measured by how effectively they build a best-in-class Office of the CEO over the first six to twelve months.

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This is a full-time, VP-level position based in one of the organization’s two national offices (Hillsboro, OR or Chelmsford, MA), on a hybrid basis with several days each week on site. The role includes periodic travel between the two offices.

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Responsibilities

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Business Planning & Management

• Establish and maintain foundational operating systems: planning frameworks, communication cadences, accountability structures, and meeting rhythms for the executive team and the leadership team beneath it.
• Drive alignment and decision velocity at the top, keeping priorities focused across a newly merged leadership team; lead prioritization and realignment as goals evolve.
• Support the CEO in setting, tracking, and following through on enterprise priorities.
• Own and drive special projects end to end, making things happen in a complex, multi-site environment.
• Partner with the leadership that owns enterprise integration to ensure executive oversight, visibility, and alignment.

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Change Leadership & Transformation

• Serve as a steady force for change across the organization, helping the executive team build a shared understanding of major transitions and translating them into a clear, organized body of work.
• Help leadership align on priorities and sequencing as the organization continues to integrate and grow - anticipating what complex transformation can miss and getting ahead of it.
• Bring structure and a proven toolkit to organizational change, establishing the operating rhythms and ways of working that allow a newly combined organization to move forward with cohesion.
• Partner with the executive team to embed change durably, ensuring new structures, cadences, and decisions take hold across both offices and cultures.

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Communications & Executive Presence

• Build and own Office of the CEO communications, including drafting executive communications on the CEO’s behalf.
• Create the systems and cadences that cascade decisions and priorities across the organization, so the broader team consistently understands what leadership is working on and why.
• Ensure meetings are well-run: agendas set, decisions and actions captured, follow-ups tracked, and relevant information shared appropriately.
• Prepare executive- and board-level materials, partnering closely with the team that manages board and supervisory-committee relations.
• Serve as the connective tissue across the executive team, bringing a diplomatic, tactical, and empathetic presence to every interaction.

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Performance Visibility & Reporting

• Build and maintain an executive dashboard, integrating financial, operational, and integration KPIs into a single, holistic view.
• Establish a consistent management-reporting cadence that gives the CEO and leadership real-time insight into performance and progress against goals.
• Support the monitoring of enterprise performance against targets.

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Operational Management & Team Alignment

• Strategically manage the CEO’s time, calendar, and stakeholder engagement with intentionality, judgment, and nimbleness.
• Lead and develop two direct reports along with the broader support team.
• Develop the support team toward project-management and business-analyst capabilities, leveraging AI and modern tools to elevate how executives across the organization are supported.
• Create the operating rhythms, systems, and cascades that scale as the organization continues to grow and transform.

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Minimum Qualifications

• 10+ years of professional experience, with meaningful time as a Chief of Staff or in a senior strategic-operations, transformation, or change-leadership role.
• A demonstrated track record of leading organizations through change, transformation, and transition.
• The gravitas and interpersonal skill to earn the confidence of a senior, newly merged executive team and to lead through influence.
• A proven ability to balance strategy with execution, translating direction into delivered results.
• Strong project-management discipline and a business-analyst / data-synthesis orientation; comfortable synthesizing information and structuring it for executive decision-making.
• Executive-grade written and verbal communication, with the ability to produce board- and C-suite-level materials with clarity, precision, and strong visual storytelling.
• Comfort leveraging AI and modern tools to drive efficiency and elevate the support model.
• A bachelor’s degree or equivalent professional experience; capability and skill set are valued most.

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Preferred Skills & Attributes

• Experience in financial services or an adjacent, heavily regulated industry such as insurance.
• Experience with M&A or post-merger integration.
• Experience standing up or maturing a Chief of Staff / Office of the CEO function.
• Experience operating within complex, multi-site, or newly merged organizations.

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Compensation

VP-level. DOE $250,000–$300,000/yr base + 30% target annual bonus.

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What are the Benefits of Joining Our Client's Team?

Our client offers a comprehensive, total rewards program. Highlights include:

• Comprehensive medical, dental, and vision coverage, with multiple plan options and strong preventive and behavioral-health benefits.
• A generous 401(k) with a substantial employer match and additional discretionary contribution, plus financial-planning support.
• Unlimited paid time off for VP-level and above, paid holidays, and paid parental leave.
• A distinctive lending benefit: a meaningful rate discount on mortgage, auto, and other consumer loans.
• Education and tuition assistance, plus dedicated paid professional-development time.
• Company-paid life and disability insurance, plus voluntary accident, critical illness, and hospital indemnity options.
• Flexible spending accounts, an Employee Assistance Program, wellbeing programs, and a range of additional perks and discounts.
• Specific plans are determined by your office location.