Senior Chief of Staff

Job Title: Senior Chief of Staff

About Company:

Our company is leading the transformation of the employee benefits industry by combining innovative technology with personalized, data-driven consulting. Our solutions are designed to be thoughtful, personalized, and engaging. Our approach empowers our clients by simplifying complex information into easy-to-understand insights that benefit companies, their employees, and the families participating in their benefit plans.

Position Overview:

Are you a strategic leader with a knack for turning vision into action, driving operational excellence, and fostering a culture of innovation and accountability? As the Chief of Staff, you will be the driving force behind aligning with the company's vision with actionable plans, ensuring efficient execution across the organization. Partnering closely with the CEO and senior leadership, you will play a pivotal role in fostering a culture of innovation, proactive problem-solving, and promoting innovation and ownership within the team.

This Position is right for you if:

You have a growth mindset and a genuine curiosity about the evolving landscape of employee benefits, technology, and leadership. You continuously seek opportunities for learning and improvement, for both you and those around you. You thrive in a dynamic environment where change is the norm and challenges are seen as opportunities for growth. Your resilience, influence, and adaptability help you navigate uncertainty and keep the team focused on achieving results.

Key Responsibilities:

· Business Acumen: Leverage a deep understanding of business operations, financials, and strategic planning to translate complex challenges into actionable initiatives that drive growth and efficiency.

· Operational Leadership: Ensure alignment across all functions, driving company-wide initiatives, and implementing tech-enabled solutions to enhance efficiency and compliance.

· Project Management & Execution: Oversee and manage complex, cross-functional projects from start to finish, ensuring thorough follow-through and attention to detail.

· Strategic Integration: Act as the key link between vision and execution, refining and implementing strategies that align with organizational goals and ensure seamless execution.

· Executive Leadership: Serve as the CEO’s most trusted advisor, providing strategic

direction, influencing senior leadership, and fostering collaboration among the executive team.

· Cultural Leadership: Promote a culture of intrapreneurship and cross-generational

collaboration, empowering team members to innovate and take initiative in driving success.

· Technology Adoption & Innovation: Lead technology automation and transformation efforts, promoting the use of innovative tools that enhance operational efficiency and drive business outcomes.

· Direct Communication & Conflict Resolution: Leverage your IQ and EQ to facilitate transparent communication across all levels, engage in difficult conversations constructively, and address challenges head-on.

· Stakeholder Management: Build and maintain strong relationships with key stakeholders, including employees, clients, and external partners, ensuring a collaborative and inclusive environment.

· Organizational Agility: Navigate complex situations with resilience and adaptability, maintaining a results-oriented mindset and achieving goals despite challenges.

Qualifications:

· Proven experience in a senior Chief of Staff role or similar operational leadership position, with the ability to act as a trusted advisor and confidant to the CEO.

· Strong project management skills with a track record of executing complex initiatives and achieving results.

· Ability to influence and lead senior leadership teams, providing strategic guidance and driving alignment across functions.

· Proactive mindset and comfort with challenging leadership, offering constructive feedback and driving better decision-making.

· Tech-savvy with experience in technology adoption and promoting innovation within teams.

· Grit, resilience, and adaptability, particularly in fast-paced and dynamic environments. Nice to Haves, but Not Requirements

• Prior business consulting experience coupled with real-world company-side experience and execution.

• Experience in a role as an integrator, operator, and/or Chief of Staff scaling a business (ideally $5-50m).

• Industry experience in employee benefits, tech/digital transformation, insurance, and/or professional services.

• Familiarity with EOS, Scaling Up, Lean Six Sigma or other business operating systems.

Location: Austin, TX

We offer a competitive relocation stipend to help ease the transition for candidates moving

from outside the area. Details of the relocation package will be discussed during the offer

stage and can be tailored to individual needs.

Compensation and Benefits:

· Base Salary: $145,000 $200,000 annually, depending on experience.

· Performance Bonus Eligibility: Annual bonuses tied to personal performance, achieving results, and company success.

· Benefits: Comprehensive health, dental, vision, life, and disability insurance, 401k match, paid time off, and flexible work arrangements.

· Work Environment: Hybrid work schedule with an emphasis on in-office collaboration with the CEO; travel up to 3 days per month.

Join us to be part of a company where your leadership will make a meaningful impact. Apply today and drive innovation in the employee benefits industry!