Chief of Staff VP Operations Marketing Advertising eCommerce

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Chief of Staff VP Operations Marketing Advertising eCommerce based in United States.

This is a high-impact executive leadership role supporting the CEO and Senior Leadership Team of a rapidly scaling DTC digital marketplace.
You will translate strategic vision into clear priorities, operating rhythms, and measurable execution across the organization.
The role sits at the intersection of strategy, operations, technology, marketing, advertising, and eCommerce.
You will serve as a trusted advisor, sounding board, gatekeeper, and execution leader for the CEO's most critical priorities.
The environment is highly AI-native, with a strong focus on using technology and automation to transform workflows and operating processes.
You will influence company-wide decision-making, executive communication, board engagement, and major strategic initiatives.
This opportunity is ideal for an experienced operator who thrives in fast-growth environments and enjoys turning complex challenges into focused action.

Accountabilities:

You will work closely with the CEO and executive leadership to increase organizational focus, accelerate execution, and ensure strategic priorities translate into measurable business outcomes.

• Translate CEO and Board vision into clear priorities, OKRs, operating plans, and execution roadmaps.
• Drive cross-functional strategic initiatives and establish an effective operating cadence across the Senior Leadership Team.
• Serve as a trusted partner, sounding board, and execution lead for the CEO on sensitive and high-priority matters.
• Prepare the CEO for Board meetings, investor discussions, and key stakeholder engagements, including research, briefing materials, and decision support.
• Provide strategic analysis, research, and recommendations to support complex business decisions.
• Act as a communication bridge across executive functions, ensuring alignment, clarity, and timely follow-through.
• Lead high-impact special projects involving business scaling, M&A, market expansion, organizational transformation, and other strategic priorities.
• Run executive and Senior Leadership Team meetings, ensuring decisions, actions, owners, and deadlines are clearly documented and followed through.
• Track organizational priorities, business metrics, accountability, and execution progress.
• Draft and coordinate internal and external executive communications.
• Coordinate Board and investor materials and ensure senior stakeholders have the information required for effective decision-making.
• Identify and resolve cross-functional blockers while proactively surfacing risks and closing execution gaps.
• Own CEO-specific initiatives from strategy through completion, maintaining momentum and accountability throughout.
• Identify opportunities to leverage AI and emerging technologies to improve executive workflows, operating processes, and organizational efficiency.

Requirements:

The ideal candidate is a highly experienced strategic operator with a strong understanding of digital commerce, customer acquisition, performance marketing, and fast-scaling organizations.

• 7–12+ years of experience supporting CEOs, Founders, or senior executives in fast-scaling small and medium-sized businesses.
• Demonstrated experience helping scale organizations of approximately 100–300 employees, ideally with experience doing so across at least two companies with 3+ years of tenure at each.
• Strong understanding of DTC customer acquisition and retention, eCommerce, performance advertising, and digital marketplace business models.
• Experience with go-to-market and target operating models across digital commerce, advertising, marketing, subscription, or membership businesses.
• Experience with web and/or mobile app-based businesses is highly valued.
• Board-level confidence, including experience preparing meetings and materials, supporting investor interactions, and handling highly confidential information.
• Strong strategic thinking combined with excellent execution, organization, and follow-through.
• Exceptional communication skills and the ability to operate effectively across executive, operational, and functional teams.
• AI-native and highly tech-savvy, with hands-on experience using modern AI tools such as Claude Code or comparable technologies at an intermediate to advanced level.
• Experience working within an AI-native organization or as an early adopter of AI-driven workflows and automation is strongly preferred.
• Ability to identify opportunities where AI can replace or enhance manual processes, SOPs, and workflows.
• Comfortable operating with significant autonomy in a fast-moving, high-growth environment.
• Passion or professional interest in eLearning, online training, sporting goods, health, wellness, fitness, or biohacking is a potential cultural fit.
• Interest in golf is a plus.
• Must be based in the United States or Canada and able to work fully remotely.

Benefits:

• Base salary of $170,000–$240,000 USD .
• Additional performance-based bonus.
• Comprehensive executive-level compensation package.
• Fully remote position.
• Opportunity to work directly alongside the CEO and Senior Leadership Team of a high-growth digital marketplace.
• Exposure to major strategic initiatives including scaling, M&A, market expansion, and AI transformation.
• Opportunity to help shape AI-first operating models and next-generation executive workflows.
• High level of autonomy, influence, and ownership across the organization.
• Permanent full-time leadership opportunity.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

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We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.