Head of Executive Operations (Chief of Staff)

Jiffy.com; United States; Remote; USD 80,000 - 150,000; Full time

Job summary

An innovative e-commerce company is seeking a proactive Head of Executive Operations to support the President and CEO. This role offers a unique opportunity to work closely with top executives, driving strategic initiatives and optimizing operational processes. With a focus on leadership development, candidates will engage in a dynamic environment that fosters growth and innovation. The position promises a rewarding career path, with mentorship from industry leaders and the chance to shape the future of e-commerce solutions. If you're ready to make a significant impact in a rapidly growing company, this role is for you.

Benefits

Mentorship from Industry Leaders

Equity in the Company

Remote Work Flexibility

Opportunity for Product Innovation

Collaborative High-Growth Environment

18-Month Growth Plan

Qualifications

• 2-3 years in top-tier management consulting or VC environment.
• 4-6 years in DTC e-commerce preferred.

Responsibilities

• Work closely with the President and CEO to align on objectives.
• Maximize executive potential by managing lower-priority tasks.
• Collaborate with teams for effective execution of strategic projects.

Skills

Strategic Thinking

Project Management

Communication Skills

Organizational Skills

Adaptability

Process Optimization

Financial Analysis

Emotional Intelligence

Education

Bachelor's Degree in Business

MBA from a Top-Tier Program

Tools

PowerPoint

Job description

Description

JiffyShirts is seeking a dynamic and proactive leader as the Head of Executive Operations (Chief of Staff). This role serves as a close advisor and right hand to the President (Peter Gerstberger, former Chief Digital & Strategy Officer at The Honest Company, ex-Amazon, and ex-Ring leadership) and facilitates the effectiveness of the executive team, including the CEO. The role involves around-the-clock exposure to daily operational functions, ensuring strategic objectives are met, streamlining processes, and optimizing productivity. The Head of Executive Operations will travel globally with the President and CEO, following a demanding schedule across multiple time zones, providing insights into their priorities, communications, strategic thinking, decision-making, management, and leadership. The position involves executing multiple cross-functional strategic initiatives. The ideal candidate will possess strategic thinking, executive presence, organizational skills, process optimization, project management, communication skills, and adaptability to the President’s style and vision. An 18-month growth plan is included, aiming to develop the candidate into a future leader with P&L responsibility within the company.

Candidates must reside in ET or CT timezone.

Key Responsibilities:

1. Work closely with the President and CEO to understand their objectives, priorities, strategic thought process, communication style, and decision-making process.
2. Maximize the President and CEO’s potential by taking ownership of lower-priority tasks to free up their time for high-value activities.
3. Collaborate with cross-functional teams to ensure effective execution of strategic initiatives and projects.
4. Develop a deep understanding of the company's operations, culture, and goals to provide insights and recommendations for sustained growth and innovation.
5. Refine and optimize processes and project management disciplines to enhance organizational efficiency.
6. Analyze financial and operational data to support strategic decisions and identify improvement areas.

Requirements

Preferred Qualifications:

• Bachelor's degree in business, management, or related field; MBA from a top-tier program preferred.
• 2-3 years of experience in a top-tier management consulting firm or VC environment (e.g., Bain, BCG, McKinsey).
• 4-6 years of experience in a DTC e-commerce company is highly preferred.
• Strong written and verbal communication skills, with adaptability to various stakeholders.
• Understanding of end-to-end business operations.
• High emotional intelligence and ability to build positive relationships across all levels.
• Excellent PowerPoint and presentation skills, with experience presenting to senior executives.
• Exceptional organizational and multitasking skills, capable of handling complex projects.
• Proven success in managing special projects, project management, and financial modeling.
• Detail-oriented, process-driven, with a focus on workflow optimization.
• Willingness to operate on an intensive schedule while traveling globally (15%).
• Ability to work independently, take initiative, and make informed decisions.

Benefits

Why you’ll love working here:

• Mentorship and exposure to leaders like Peter Gerstberger and Chris Serflek.
• Equity in a rapidly growing, founder-owned, fully bootstrapped company with a 9-figure topline and 8-figure EBITDA.
• Remote work flexibility with a high-performing team.
• Impact in shaping innovative e-commerce solutions.
• Opportunity to lead product innovation in AI and image processing.
• Collaborative, high-growth environment with strategic influence.
• 18-month growth plan with potential to become a P&L leader.