Vannin Chief of Staff has been retained by a fast-growing compliance training company recognized for award-winning products, workplace culture, and trusted by thousands of organizations worldwide.

Our client is seeking a Chief of Staff to serve as a key member of their leadership team. Reporting directly to the CEO, this role will interface with the executive team, drive strategic initiatives, and ensure accountability for goals across the company. The ideal candidate combines strategic thinking with exceptional execution discipline, possessing strong business acumen and the ability to influence without formal authority.

This is a full-time, fully remote, exempt position offering significant growth opportunity in a fast-paced, PE-backed environment.

Responsibilities

Executive Leadership & Operations (50%):

• CEO Partnership: Act as strategic thought partner to the CEO, assisting with day-to-day operational management and ensuring CEO priorities are effectively executed across the organization

• Meeting Excellence: Enhance effectiveness of executive meetings by setting strategic agendas, driving high-quality content and outputs, and ensuring robust follow-up on action items

• EOS/Traction L10 Facilitation: Lead quarterly OKR processes and Traction EOS implementation

• Operational Rhythm: Own and continuously improve company operating cadence including executive team meetings, leadership offsites, quarterly business reviews, and board meeting preparation

• Performance Management: Develop and monitor key business metrics, KPIs, and scorecards; identify and flag areas of concern with actionable recommendations

• Executive Communications: Lead preparation and development of executive presentations including board meetings, investor relations, all-hands meetings, and external speaking engagements

• Board Support: Drive board meeting preparation, take detailed notes, create follow-up action logs, and track completion of strategic initiatives

Strategic Project Leadership & Special Initiatives (50%):

• Cross-Functional Initiative Ownership: Lead and coordinate complex, multi-functional strategic initiatives under tight timelines, managing competing priorities and driving accountability across teams

• Revenue Organization Focus: Support strategic projects within our 90-person revenue organization, with particular emphasis on customer success, retention, and net revenue retention initiatives

• Interim Leadership: Provide leadership coverage during executive absences or role transitions

• Process Innovation: Identify opportunities for operational improvement and innovation to drive business efficiency and growth

• Special Projects: Execute high-priority initiatives including AI strategy development, market expansion projects, and organizational improvement initiatives

• Change Management: Drive organizational changes and process improvements while maintaining team morale and productivity

• Stakeholder Alignment: Facilitate communications between leadership and the broader organization, ensuring alignment and transparency

Required Qualifications

Education & Experience:

• Bachelor's degree required; MBA preferred

• Must have held a Chief of Staff title previously

• 5+ years of experience including:

  • Investment banking OR management consulting experience

  • Private equity or fast-paced scaling technology company experience

• Experience in customer success or revenue operations functions strongly preferred

Core Competencies:

• Strategic Thinking: Ability to see multiple moves ahead, understand complex trade-offs, and pressure-test executive thinking with structured frameworks

• Execution Discipline: Relentless follow-through with ability to hold senior leaders accountable while maintaining relationships

• Communication & Influence: Exceptional ability to gain buy-in from strong personalities and synthesize complex issues clearly for diverse audiences

• Business Acumen: Deep understanding of P&L drivers, customer dynamics, competitive landscape, and key business metrics

• Confidentiality & Discretion: Proven ability to handle sensitive CEO, board, and personnel matters with absolute confidentiality

Behavioral Requirements:

• Executive Presence: Comfort operating at C-suite and board level with ability to establish credibility and influence without formal authority

• Emotional Intelligence: High EQ with ability to read room dynamics, adapt communication style, and facilitate productive conflict resolution

• Resilience: Comfort with executive-level debate and challenging discussions; ability to maintain composure under pressure

• Proactive Problem-Solving: Identifies and resolves critical issues before escalation; knows when to handle independently vs. escalate

• Energy & Drive: High energy with healthy drive toward accountability and completion of key initiatives

Technical Skills:

• Excellent written, verbal, and presentation communication skills

• Strong quantitative and analytical capabilities with attention to detail

• Experience with EOS/Traction and Ninety 90 software preferred but not required

• Ability to manage multiple time-sensitive workstreams simultaneously

Additional Requirements:

• Travel: ~10%

• Location: 100% remote (Kansas City preference but not required)

Compensation

Base Salary: $175,000 - $200,000 annually

Bonus: 30% target bonus

Benefits: Comprehensive package including medical, dental, vision, 401K with company match, unlimited PTO, 3:00 PM Friday head start, parental leave, and Employee Assistance Program

What to Expect from Our Selection Process:

We are seeking passionate operators who possess the ability to move from strategy to tactical smoothly to join our leadership team. Our selection process is designed to assess the whole candidate and foster a mutual match for you and us. The process includes:

Vannin Screening: 15-minute phone interview & 30-minute video interview

Client Interview 1: Virtual interview with Head of HR

Client Interview 2: Virtual interview with CEO

Client Interview 3: Virtual panel interview with executive leadership team

Client Interview 4: Case study interview with CEO (onsite in Kansas City)


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 group