VP, Chief of Staff (Remote)

TruStage; United States; Remote; USD 180,000 - 240,000; Full time

Benefits offered by this job

Annual bonus

Medical coverage

Dental coverage

Vision coverage

401k plan

Life insurance

Parental leave

Paid time off

Tuition reimbursement

Job summary

TruStage seeks a strategic Chief of Staff to the President & CEO to align enterprise priorities, accelerate execution, and deliver meaningful outcomes across the organization. This role blends advisory, operations, and leadership across functions, boards, and partners, with a development rotation in 12–24 months.

Ideal candidates will have 10–15+ years in insurance/financial services, executive leadership experience in complex settings, and a proven track record of enterprise transformation.

Qualifications

• 10–15+ years of experience in insurance/financial services or related management/consulting background.
• Experience leading organizational or enterprise transformation.
• Executive leadership experience in a complex organization, including work with executive teams or boards.

Responsibilities

• Serve as a trusted advisor to the CEO on enterprise priorities, risks, opportunities, and decisions.
• Shape executive discussions and manage stakeholder engagements with the Executive Team, Board, and partners.
• Drive alignment and execution of enterprise priorities across the organization.

Skills

Strategic thinking

Executive leadership

Cross-functional collaboration

Business acumen

Job description

At 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 recognition

Job 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 governance

Job 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-LT

At TruStage, we believe a sound, inclusive benefits program is of vital importance, along with a flexible workplace that allows for work-life balance, career growth and retirement assistance. In addition to your base pay, your position may be eligible for an annual incentive (bonus) plan. Additional benefits available to eligible employees include medical, dental, vision, employee assistance program, life insurance, disability plans, parental leave, paid time off, 401k, and tuition reimbursement, just to name a few. Beyond pay and benefits, we also recognize that flexibility, including working in a place you prefer, is essential to caring for our employees. We will continue to strive to offer flexibility and invest in technology and other tools that will make hybrid working normal rather than an exception, so that when "life happens," you can focus on what's most important.

Accommodation request

TruStage is a place where everyone can bring their best self and thrive. If you need application or interview process accommodations, please contact the accessibility department.