Chief of Staff Strategy Operations Director VP

Chief of Staff alongside and supporting the CEO Founder, COO, CFO, CMO, COO, CTO, (USA, Remote based). I’m leading an executive search for a $100MM+ high-growth DTC digital marketplace, on a clear path to $500MM+ revenue in the next few years. This role is designed to amplify the CEO and SLT - optimizing time, focus, decision-making, and execution across the Senior Leadership Team.

You operate seamlessly between strategy and action: trusted partner, gatekeeper, sounding board, and execution lead for the CEO’s most sensitive priorities. Those with a career history in digital and eCommerce, advertising and marketing operations will have stand out knowledge as they have a better than agency internal team for those functions.

You’re an AI-native and tech-savvy, using tools like Claude Code or similar daily at an intermediate–advanced level and certainly come from that type of company environment eg AI native or early adopters as this business aims to become AI first (where appropriate). This client has an AI technical team for programming your workflow requirements of the SLT and their teams, where human first SOPs are being replaced.

Your Profile

• Strong D2C customer acquisition and retention, eCommerce, performance advertising and digital marketplace understand and experience of those GTM and TOMs including subscription and membership growth (web or mobile apps)

• Passion for eLearning, online training, sporting goods, health, wellness, fitness, or biohacking could be a good culture fit

• 7–12+ years supporting CEOs/Founders in fast-scaling SMBs

• Experience scaling a 100–300 person company (ideally 2+ examples each with 3+ years tenure)

• Board-level confidence: meetings, materials, investors, confidentiality

• USA/CAN-based, fully remote

• Interested in golf

Core Responsibilities

• Translate CEO & Board vision into priorities, OKRs, and execution plans

• Drive cross-functional initiatives and operating cadence

• Prepare CEO for board, investor, and key stakeholder engagements

• Provide research, analysis, and decision support

• Act as communication bridge across the executive team

• Lead high-impact special projects (scale, M&A, market entry)

Day-to-Day

• Run executive and SLT meetings with clear follow-through

• Track priorities, metrics, and accountability

• Draft CEO communications (internal & external)

• Coordinate board and investor materials

• Resolve cross-functional blockers