The Chief of Staff Association has been retained by a specialty insurance and nonprofit CPA firm known for deep technical expertise, a long-tenured leadership team, and a strong, relationship-driven culture; many of the firm’s partners have been with the firm for 20+ years. The firm’s Innovation and Technology group, led by Chief Innovation Officer, is growing quickly, generating strong ideas for AI and technology adoption and driving the next chapter of the firm’s operational transformation.

Chief of Staff Role

Our client is seeking a chief of staff for a newly created position on the leadership team, reflecting the firm's growing investment in AI and technology transformation. Reporting to the Chief Innovation Officer, this individual will translate his vision into firmwide execution, aligning stakeholders, driving the operating cadence, and delivering critical initiatives across the Innovation and Technology organization. While working closely with the CIO day to day, the role is also accountable for keeping Innovation and Technology initiatives aligned with the firm's strategic plan as set by the Executive Committee. The ideal candidate is a proven leader with a blend of strategic, operational, project management, and leadership skills. Additionally, they should possess exceptional attention to detail, initiative, and critical thinking skills. They are curious, adaptable, and comfortable managing change and ambiguity. They enjoy solving complex problems, are highly collaborative, and operate with a strong bias toward action and results. They exercise exceptional discretion with confidential information, and are comfortable pushing back, with grace, when priorities need to be protected.

This will be a full-time, exempt position based remotely in the Eastern or Central time zone, with up to 10% travel on the East Coast, US.

Responsibilities

Executive Team Leadership and Company Strategy:

• Partner with the Chief Innovation Officer to translate his vision for AI and technology transformation into clear, actionable plans that also reflect the firm's broader strategic direction, helping him prioritize where he spends his time; be a trusted right hand who ensures priorities are being effectively executed and remain aligned with firmwide strategy

• Own prioritization and execution of key technology and AI initiatives, partnering with the CIO and cross-functional teams (including IT, Quality Management, and Audit) to move ideas from concept through completion

• Bring structured judgment and the confidence to push back, evaluating trade-offs when new ideas surface and helping the team stay focused on the highest-priority work and flagging when new ideas may be drifting from the firm's strategic plan

Operations:

• Own and continuously improve the operating cadence within the Innovation and Technology organization, running (not just attending) recurring meetings, tracking action items, and ensuring follow-through

• Lead critical initiative delivery and special projects, such as workflow automation tools supporting the audit framework, coordinating across IT and Quality Management to keep cross-functional work on track

• Manage the technology and AI project pipeline, flag bottlenecks (e.g., engineering capacity constraints), and help build the structure needed to scale as the organization grows

Communications:

• Amplify the CIO’s time and impact by auditing his calendar, filtering out low-value asks, and freeing him to focus on high-value strategic and innovation work

• Distill and translate the CIO’s ideas into clear, actionable messages for stakeholders across the firm, helping communicate the “why” behind change and drive broader adoption and buy-in

• Partner closely with the Chief Operating Officer on cross-functional coordination between Innovation and Technology and the rest of the firm, and with the Managing Partner on communications to the executive committee and partner group

Recommended Minimum Qualifications

• 8+ years of professional experience in management consulting, audit, or a similar professional-services environment

• Proven experience as a chief of staff, business operations leader, or similar role supporting a senior executive, ideally within a technology or AI-driven organization

• 3+ years of project and change management expertise, with a track record of taking initiatives from idea through completion

• Demonstrated analytical and problem-solving skills, with the judgment to evaluate trade-offs and prioritize competing initiatives

• Excellent verbal and written communication skills, with the presence to work directly with C-suite executives

• Excellent Microsoft Office/GSuite skills

• Demonstrated, active fluency with AI tools and technology in daily work (e.g., using AI assistants and modern SaaS tools to manage tasks and communication)

Preferred Skills & Attributes

• Proven ability to juggle multiple projects and meet tight deadlines, showcasing strong ownership, organizational, and time-management capabilities under pressure

• Skilled in professional and diplomatic written and verbal communication, capable of engaging effectively with a diverse range of internal and external stakeholders with high executive presence

• Self-starter and self-motivated with a proactive approach to identifying and addressing issues

• A natural curiosity to deepen knowledge of AI automation and data trends over time, beyond day-to-day tool use

• Comfort in operating with dual accountability, day-to-day partnership with an executive sponsor while keeping outcomes aligned to broader organizational strategy

• The maturity to first learn a new organization's culture and ways of working, then bring fresh perspective and ideas once grounded in how the firm operates as a partner-led organization

• Based in, or willing to work within, the Eastern or Central time zone; open to occasional travel (no more than monthly) for in-person collaboration with the team

Compensation Range: DOE $165,000 - $180,000 USD annual base salary + profit sharing

What Are The Benefits of Working with Our Client?

Our client offers a comprehensive benefits package designed to support employees and their families, including medical, dental, and vision coverage; an employer-funded Health Savings Account; 100% employer-paid life insurance and long-term disability coverage; a 401(k) plan with company match; a Dependent Care Flexible Spending Account; a Lifestyle Spending Account for personal wellbeing; an Employee Assistance Program; and pet insurance, among other offerings.

Beyond the benefits package, employees join a firm known for its long-tenured, relationship-driven culture, where people are genuinely supported and invested in for the long term.

As part of this placement, the new hire will also receive: three months of executive coaching; and a one-year membership in the Chief of Staff Association, with access to executive education and a 1,500+ member peer network.

What to Expect from Our Selection Process

The process includes:

1. The Chief of Staff Association Predictive Index Behavioral Assessment
2. The Chief of Staff Association: 15 min phone interview & 30 min video interview
3. Client Interview 1: Virtual interview with CIO
4. Client Interview 2: Virtual panel interview with COO and Managing Partner
5. Client Interview 3: Virtual case study interview with senior leaders

*Note: The Chief of Staff Association partners with The Predictive Index to align workstyles with the role. All applicants complete this quick, two-question, five-minute assessment, no right or wrong answers, and receive a profile readout.

--> Please take the assessment here as you complete your application. 

Our client is committed to creating and maintaining a diverse and inclusive workplace where our employees can thrive and be themselves! We welcome all persons into our community. We embrace the diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental disabilities, medical condition, genetic characteristic, sexual orientation, marital status, family care or medical leave status, military or veteran status, or perceived membership in any of these groups.