VP, Chief of Staff (Remote)

Praxy; Northern (KY); Hybrid; USD 180,000 - 260,000; Full time

Job summary

TruStage is seeking a strategic, enterprise-minded Chief of Staff to the President and CEO. This role goes beyond traditional executive support, serving as trusted advisor, operational integrator, and partner to drive high-impact priorities across the organization.

The Chief of Staff will shape executive discussions, drive alignment, translate decisions into action, and build cross-functional relationships to accelerate outcomes in a dynamic, regulated financial services environment.

Qualifications

• 10–15+ years in insurance/financial services or related consulting.
• Experience guiding enterprise transformation.
• Executive leadership in a complex organization or with executive teams/board governance.

Responsibilities

• Serve as trusted advisor to the CEO on priorities, risks, opportunities, and decisions.
• Shape executive discussions and key stakeholder engagements, including Board interactions.
• Drive alignment and execution of enterprise priorities across the Executive Team and business units.
• Translate decisions into clear ownership, plans, milestones, and measurable outcomes.

Skills

Strategic thinking

Cross-functional leadership

Executive communication

Influence without authority

Enterprise problem solving

Job description

# VP, Chief of Staff: Remote - USA: Oct 3, 2026: Oct 4, 2026## About the roleAt TruStage, we’re on a mission to make a brighter financial future accessible to everyone. We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future.Join a team that has received numerous awards for being a top place to work: TruStage awards and recognitionJob Purpose:TruStage is seeking a strategic, enterprise-minded leader to serve as Chief of Staff to the President and CEO. This role is far more than project management or executive support. The Chief of Staff serves as a trusted advisor, operational integrator, strategic thought partner, and enterprise problem solver who helps the CEO and Executive Team focus on the highest-value priorities and deliver meaningful outcomes across the organization. The successful candidate will help ensure that critical initiatives move forward with clarity, accountability, and speed while enabling the Executive Team to operate as one enterprise.The position is ideal for a leader who thrives in complex environments, can navigate ambiguity, builds trust quickly, influences without authority, and translates strategy into action. This is a developmental role, where the incumbent in this role will rotate into another position in the organization in a 12–24-month timeframe.Job Responsibilities:- Serve as a trusted advisor and strategic thought partner to the CEO on enterprise priorities, risks, opportunities, and decisions.- Shape executive discussions and key stakeholder engagements, including Executive Team, Board, and partner interactions.- Drive alignment and execution of enterprise priorities across the Executive Team and business units.- Translate decisions into clear ownership, plans, milestones, and measurable outcomes.- Identify barriers, dependencies, and resource needs; facilitate timely resolution.- Strengthen Executive Team operating rhythms, decision-making, accountability, and follow-through.- Create transparency across priorities, risks, dependencies, resource needs, and progress.- Bring structure, analysis, and sound judgment to complex or ambiguous enterprise issues.- Build trusted cross-functional relationships that accelerate collaboration and outcomes.The above statement of duties is not intended to be all inclusive and other duties will be assigned from time to time.Preferred Qualifications:- Experience in financial services, insurance, banking, technology, consulting, or another regulated industry.- Experience leading organizational, cultural, or enterprise transformation.- Executive leadership experience in a complex organization, including work with executive teams or board governanceJob Requirements:- 10-15+ years of experience in insurance/ financial services industry or background in business management or consulting experience- Demonstrated leadership through a major business event.- Demonstrated ability to contribute to executive decision-making, enterprise alignment, communication, and execution under pressure and uncertainty.- Ability to operate effectively across functions and connect strategy, operations, finance, risk, talent, technology, and customer outcomes.- Ability to connect long-term strategy to near-term execution, priorities, accountability, and measurable results.- Ability to build trust, influence without direct authority, and create alignment across diverse stakeholders and perspectives.- Ability to communicate complex issues clearly and simply through executive, board, verbal, written, and presentation materials.- Enterprise-minded, decisive, resilient, intellectually curious, and comfortable operating in ambiguity, complexity, disruption, and change.- Accountable for outcomes and able to challenge constructively while maintaining trust, alignment, and commitment to one TruStage.- Executive leadership experience in a complex organization, including work with executive teams or board governance, preferred.- Experience in financial services, insurance, banking, technology, consulting, or another regulated industry, preferred.- Experience leading organizational, cultural, or enterprise transformation, preferred.#LI-remote#LI-LTIf you’re ready to help make a difference, apply today. A resume is required to apply. TruStage may process applicant information using an Artificial Intelligence (AI) tool. This tool automatically generates a screening score based on how well applicant information matches the requirements and qualifications for the position. TruStage recruiters use the screening score as a guide to further evaluate candidates; the score is one component of an application review and does not automatically determine whether a candidate moves forward. Candidates may choose to opt out of this process.