Chief of Staff to CEO (Remote) — Strategy & Execution

TruStage Insurance Agency, LLC; Northern (KY); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Annual incentive bonus

Medical, dental, vision benefits

401k and retirement plan

Job summary

TruStage Insurance Agency, LLC is seeking a VP, Chief of Staff (Remote) to partner with the President and CEO, aligning enterprise priorities and driving decisive action across the organization. You will translate strategy into execution, shape executive discussions, and build cross-functional trust to accelerate outcomes.

The role demands 10–15+ years in insurance/financial services, executive leadership experience, and the ability to navigate ambiguity while maintaining clarity and

Qualifications

• 10–15+ years of experience in insurance/financial services industry or related business management/consulting.
• Demonstrated leadership in a complex organization and work with executive teams or board governance.
• Ability to translate strategy into action and drive enterprise alignment and execution.

Responsibilities

• Serve as trusted advisor and strategic thought partner to the CEO on priorities, risks and decisions.
• Shape executive discussions and stakeholder engagements, including Board and partners.
• Drive alignment and execution of enterprise priorities across the Executive Team and units.
• Turn decisions into clear ownership, plans, milestones and measurable outcomes.
• Identify barriers and resource needs; facilitate timely resolution.
• Strengthen operating rhythms, accountability and follow-through across teams.

Skills

Executive leadership

Strategic thinking

Cross-functional collaboration

Stakeholder management

Clear communication

Job description

TruStage Insurance Agency, LLC is seeking a VP, Chief of Staff (Remote) to partner with the President and CEO, aligning enterprise priorities and driving decisive action across the organization. You will translate strategy into execution, shape executive discussions, and build cross-functional trust to accelerate outcomes.

The role demands 10–15+ years in insurance/financial services, executive leadership experience, and the ability to navigate ambiguity while maintaining clarity and