Chief of Staff to CEO

Location: Hybrid work schedule- partially in office in Portland, Oregon

Our client is dedicated to helping customers achieve financial well-being and peace of mind as a leading provider of financial protection products, workplace benefits, and services for employers and individuals. Founded in 1906 with the mission to contribute to the community's well-being by providing local services to local people, today it maintains this spirit with a proud commitment to community everywhere their employees work and live, nationwide.

The Chief of Staff serves as a bridge between the CEO and the organization, extending their reach, advancing strategic initiatives, and collaborating with the Executive Leadership Team to drive organizational efficiency and key priorities.

Serving as a key facilitator, the Chief of Staff oversees complex, cross-functional projects, monitors strategic priorities, and cultivates strong relationships across teams to enhance organizational effectiveness. They provide structure and support, enabling executives and teams to operate with clarity and efficiency.

This role will manage, lead, and mentor a team of Executive Assistants , driving operational alignment and fostering professional development.

As the CEO's trusted liaison, the Chief of Staff serves as a central point of coordination , streamlining the flow of critical information, managing the CEO's calendar and priorities , and ensuring that leadership remains focused on the highest-impact initiatives.

• Support executive team workflows, ensuring progress on strategic initiatives through structured tracking and regular follow-ups.
• Enhance communication processes to ensure timely updates, decision-making clarity, and accountability across departments.
• Prepare and manage executive team meetings, including agenda setting, materials preparation, and tracking key deliverables to drive effective follow-through.
• Establish processes to monitor enterprise-wide initiatives, ensuring alignment with long-term goals.

• Serve as a key liaison to the CEO, ensuring smooth information flow and effective communication across stakeholders.
• Optimize the CEO's time and priorities by managing schedules, coordinating meetings, and streamlining administrative tasks, ensuring the CEO's time is focused on the most strategic initiatives.
• Support decision-making by gathering, synthesizing, and presenting key industry insights and internal information to the CEO and executive team.
• Exercise the highest level of discretion and professionalism, overseeing messaging, correspondence, and priority alignment on behalf of the CEO's office.
• Ensure seamless and consistent executive communication by partnering with communications leaders to authentically reflect the CEO's voice and vision.
• Represent the CEO's office in internal and external engagements, ensuring clear communication and alignment with organizational priorities.
• Take on special projects and initiatives as directed by the CEO, ensuring that the organization's priorities are addressed and executed.

• Lead Executive Assistant team, enhancing operational efficiency, ensuring effective collaboration, and elevating collective performance.
• Develop, coach, and mentor EA team to provide support and growth while cultivating a cohesive, positive team culture.
• Facilitate cross-functional collaboration to ensure alignment between leadership, departments, and key initiatives.
• Foster strong relationships across the organization, representing the CEO's office to streamline coordination and ensure alignment.

Requirements

• Bachelor's degree required, preferably in Business Administration, Communications, Organizational Leadership, or a related field.
• Master's degree (MBA or related field) is a plus but not required.
• 8+ years of professional experience in a strategic support, operational, or facilitation role, such as Chief of Staff, Executive Business Partner, Program Manager, or similar.
• Experience working closely with senior executives, ensuring cross-functional alignment, and facilitating executive communication.
• Strong background in organizational coordination, project management, or executive operations in a fast-paced environment.
• Experience managing administrative teams.
• Exceptional communication skills ability to synthesize complex information and facilitate clear, concise messaging across teams.
• Strong organizational and project coordination abilities, ensuring efficient follow-through and tracking of initiatives.
• Proficiency in productivity and collaboration tools (Google Workspace, Microsoft Office, project management software such as Asana, Monday.com, or Notion).
• Proven ability to manage competing priorities, stay adaptable, and support executives in a dynamic business environment.

Benefits

Generous Benefit Package

Qualification

Bachelor's Degree