Chief of Staff to the Founder

Role's Mission

Increase the CEO's effectiveness and the company's execution velocity by owning the leadership operating cadence, driving cross-functional initiatives and ensuring decisions translate into measurable outcomes.

Key Responsibilities

• Own executive operating rhythm: agendas, pre-reads, actions, accountability tracking.
• Partner with CEO to define annual/quarterly priorities and translate into OKRs and scorecards.
• Lead cross-functional, high-priority initiatives from scoping through delivery.
• Create decision clarity: write problem statements, options, tradeoffs, recommendations.
• Maintain "single source of truth" on strategic initiatives: roadmap, risks, dependencies.
• Prepare CEO for key meetings; draft comms for board/investors/leadership as needed.
• Identify operational friction and implement process improvements.
• Establish escalation mechanisms and ensure rapid resolution of blockers.

Success Metrics (Examples)

• On time delivery rate of top initiatives; reduction in "stalled" cross functional work.
• Improved meeting quality: fewer recurring issues, clearer decisions, faster cycle times.
• Visibility: accurate dashboards, predictable reporting, fewer surprises.
• CEO leverage: measurable reduction in CEO time spent on coordination/chasing.

Required Qualifications

• 3-5+ years in operating, consulting, banking, strategy, or high growth leadership roles (range depends on company stage).
• Demonstrated ownership of cross functional programs with measurable outcomes.
• Strong structured thinking, financial literacy, and data driven decisioning.
• Exceptional written communication (memos, briefs, narratives).
• High EQ and credibility with senior leaders; can influence without authority.
• Discretion and integrity with confidential information.

Preferred Qualifications

• Experience in the company's industry and/or scaling a private business.
• Experience with operating cadences (OKRs, MBR/QBR), KPI dashboards.
• Prior Chief of Staff (CoS), GM, Strategy & Ops, or Program Leadership experience.

Operating Style Expectations

• Bias to action; comfortable with ambiguity.
• Low ego, high standards.
• Can switch between "big picture" and "in the weeds" quickly.
• Willing to be accountable, not just advisory.

CoS Core Responsibilities CEO "Operating System"

• Run the executive meeting cadence (weekly exec, monthly business review, quarterly planning).
• Build/maintain the CEO's priorities, OKRs, and performance dashboard.
• Ensure decisions get made (clear owners, deadlines, escalation paths).
• Turn strategy into a sequenced execution plan.

Cross functional execution and unblock

• Drive alignment across leaders when work spans multiple functions.
• Identify bottlenecks early; surface tradeoffs and force resolution.
• Follow through: ensure commitments are delivered, not just discussed.

Communications and stakeholder management

• Draft CEO updates: board/investor memos, leadership narratives, critical internal comms.
• Prepare briefing docs for key meetings.
• Ensure messaging consistency across leadership.

Special projects and "keep the trains running"

• Handle urgent, ambiguous problems with incomplete data.
• Create structure where none exists: timelines, RACI, risk logs, decision records.

Common CoS Archetypes

• Execution CoS (Operator): owns key initiatives + drives cadence (most common in private companies).
• Strategy CoS: analysis, market work, narrative, board materials (more common near fundraising/M&A).
• Transformation CoS: process redesign, metrics, systems, cost/margin programs.
• People/Org CoS: org design, performance management, leadership operating model.