Head of Executive Operations (Chief of Staff)

Jiffyshirts; United States; Remote; USD 80,000 - 150,000; Full time

Job summary

An innovative company is looking for a proactive leader to serve as the Head of Executive Operations. This role provides a unique opportunity to work closely with top executives, facilitating strategic initiatives and optimizing operational processes. The ideal candidate will possess strong project management and communication skills, with the ability to adapt to a dynamic environment. With mentorship from industry leaders and a growth plan leading to P&L responsibilities, this position offers a chance to make a significant impact in a rapidly growing e-commerce firm. Remote work flexibility and a collaborative culture enhance the appeal of this exciting opportunity.

Benefits

Mentorship from industry leaders

Equity in the company

Remote work flexibility

Opportunity to lead product innovation

Collaborative high-growth environment

18-month growth plan

Qualifications

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

Responsibilities

• Work closely with the President and CEO on strategic objectives.
• Optimize processes and project management disciplines.

Skills

Strategic Thinking

Project Management

Communication Skills

Organizational Skills

Process Optimization

Financial Analysis

Emotional Intelligence

Adaptability

Education

Bachelor's degree in Business

MBA from a top-tier program

Tools

PowerPoint

Job description

JiffyShirts is seeking a dynamic and proactive leader as the Head of Executive Operations (also known as Chief of Staff). This role serves as an extension 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 effectiveness for the executive team, including the CEO.

The role involves around-the-clock exposure to the company’s daily operational functions, ensuring strategic objectives are met while streamlining processes and optimizing productivity. The Head of Executive Operations will travel globally with the President and CEO, following a demanding and intensive schedule across multiple time zones. This provides exposure to the priorities, communications, strategic thinking, decision-making, management, and leadership of the President and CEO.

The Head of Executive Operations will execute across multiple cross-functional strategic initiatives. The ideal candidate will possess strategic thinking, executive presence, organizational prowess, process optimization, project management, and communication skills, with the ability to adapt to the President’s style and vision. An 18-month growth plan is in place for the candidate to develop into a future leader with P&L responsibility within the company.

Candidates must live 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 higher-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.
5. Refine and optimize processes and project management disciplines to enhance efficiency.
6. Assemble and analyze financial and operational data to support strategic decisions and identify improvement areas.

Preferred Qualifications:

1. Bachelor's degree in business, management, or related field; MBA preferred from a top-tier program.
2. 2-3 years of experience in a top-tier management consulting firm or VC environment (e.g., Bain, BCG, McKinsey).
3. 4-6 years of experience in a DTC e-commerce company is highly preferred.
4. Strong written and verbal communication skills, adaptable to various stakeholders.
5. Understanding of end-to-end business operations.
6. High emotional intelligence and ability to build positive relationships at all levels; capable of gaining respect from the Executive Team.
7. Excellent PowerPoint/presentation skills, with experience presenting to senior executives.
8. Exceptional organizational and multitasking skills, with the ability to handle complex projects.
9. Proven success in managing special projects, project management, and financial modeling.
10. Detail-oriented, process-driven mindset focused on workflow optimization.
11. Ability and eagerness to operate on an intensive schedule while traveling globally (approximately 15%).
12. Demonstrated independence, initiative, and decision-making ability.

Why you’ll love working here:

• Mentorship and exposure to leaders like Peter Gerstberger and Chris Serflek, with extensive experience in digital strategy and ecommerce.
• Equity in a hyper-growth, founder-owned, fully bootstrapped company with a nine-figure topline and eight-figure EBITDA.
• Remote work flexibility with a high-performing team.
• Influence in shaping innovative e-commerce solutions.
• Opportunity to lead product innovation in AI and image processing.
• Collaborative, high-growth environment with a direct impact on strategic direction.
• 18-month growth plan with an exit opportunity to become a P&L leader.